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ORGANIC CHEMISTRY

SECOND EDITION
ORGANIC CHEMISTRY
AN INTERMEDIATE TEXT

SECOND EDITION

Robert V. Hoffman
New Mexico State University

A JOHN WILEY & SONS, INC., PUBLICATION

Copyright  2004 by John Wiley & Sons, Inc. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey.

Published simultaneously in Canada.

No part of this publication may be reproduced, stored in a retrieval system, or transmitted in

any form or by any means, electronic, mechanical, photocopying, recording, scanning, or
otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright
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Rosewood Drive, Danvers, MA 01923, 978-750-8400, fax 978-750-4470, or on the web at
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(201) 748-6011, fax (201) 748-6008, e-mail: [email protected].

Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their
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Wiley also publishes its books in a variety of electronic formats. Some content that appears
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Library of Congress Cataloging-in-Publication Data

Hoffman, Robert V.
Organic chemistry : an intermediate text / Robert V. Hoffman.—2nd ed.
p. cm.
Includes bibliographical references and index.
ISBN 0-471-45024-3 (cloth)
1. Chemistry, Organic. I. Title.
QD251.2.H58 2004
547—dc22
2004014949
Printed in the United States of America.

10 9 8 7 6 5 4 3 2 1
To Rose
 CONTENTS

Preface xiii

Preface to the First Edition xv

1 Functional Groups and Chemical Bonding 1

Functional Groups / 1
Orbitals / 5
Bonding Schemes / 7
Antibonding Orbitals / 13
Resonance / 18
Conjugated π Systems / 21
Aromaticity / 23
Bibliography / 26
Problems / 27

2 Oxidation States of Organic Compounds 32

Oxidation Levels / 32
Oxidation States in Alkanes / 34
Oxidation States in Alkenes / 34
Oxidation States in Common Functional Groups / 35
Oxidation Level Changes During Reactions / 35
Bibliography / 41
Problems / 41

3 Acidity and Basicity 47

Bronsted and Lewis Acids and Bases / 47

Acid Strength / 49
Acid–Base Equilibria / 53

vii
viii CONTENTS

Amphoteric Compounds / 56
Structural Effects on Acidity / 56
Electronegativity / 58
Inductive Effects / 59
Resonance Effects / 61
Bibliography / 63
Problems / 63

4 Curved-Arrow Notation 69

Electron Movement / 69
Heterolytic Bond Cleavages / 70
Heterolytic Bond Formation / 71
Homolytic Bond Making and Bond Breaking / 73
Resonance Structures / 75
Depiction of Mechanism / 76
Bibliography / 82
Problems / 82

5 Mechanisms of Organic Reactions 86

Activation Energy / 87
Activated Complex / 88
Reaction Energetics / 89
Structure of the Activated Complex / 91
Hammond Postulate / 96
Reaction Kinetics / 99
Determining Activation Energies / 104
Isotope Effects / 105
Electronic Effects / 110
Hammett Equation / 111
Bibliography / 118
Problems / 118

6 Stereochemical and Conformational Isomerism 124

Stereochemical Structures / 125

Chirality / 128
Configuration of Chiral Centers / 129
Multiple Stereocenters / 132
Optical Activity / 137
Absolute Configuration / 138
Physical Properties of Enantiomers / 139
Resolution of Enantiomers / 140
Stereoselective Reactions / 144
 CONTENTS ix

Formation of Enantiomers / 144

Formation of Diastereomers / 146
Stereochemistry to Deduce Mechanism / 152
Conformational Analysis / 157
Conformational Energies / 164
A Values / 166
Strain in Ring Systems / 167
Stereoelectronic Effects / 172
Bibliography / 176
Problems / 176

7 Functional Group Synthesis 183

Functional Group Manipulation / 183

Carboxylic Acids / 185
Esters / 188
Amides / 190
Acid Chlorides / 191
Aldehydes / 192
Ketones / 194
Imines and Imine Derivatives / 197
Alcohols / 198
Amines / 201
Alkenes / 203
Alkanes / 207
Bibliography / 208
Problems / 209

8 Carbon–Carbon Bond Formation between Carbon

Nucleophiles and Carbon Electrophiles 216

Synthetic Strategy / 217

Nucleophilic Carbon / 218
Electrophilic Carbon / 220
Reactivity Matching / 223
Generation of Nucleophilic Carbon Reagents / 224
Generation of Electrophilic Carbon Reagents / 227
Matching Nucleophiles with Electrophiles / 227
Enolates / 228
Enolate Regioisomers / 234
Diastereoselection in Aldol Reactions / 236
Organometallic Compounds / 239
Neutral Carbon Nucleophiles / 239
C=C Formation / 242
Cyclopropanation Reactions / 244
x CONTENTS

Metal-Catalyzed Carbon–Carbon Bond Formation / 246

Pd(0)-Catalyzed Carbon–Carbon Bond Formation / 247
Heck Reaction / 251
Suzuki Coupling / 253
Stille Coupling / 254
Olefin Metathesis / 256
Bibliography / 261
Problems / 262

9 Carbon–Carbon Bond Formation by

Free-Radical Reactions 272

Free-Radical Reactions / 272

Free-Radical Polymerization / 277
Nonpolymerization Reactions / 278
Free-Radical Initiation / 280
Free-Radical Cyclization / 283
Bibliography / 288
Problems / 288

10 Planning Organic Syntheses 292

Retrosynthetic Analysis / 292

Carbon Skeleton Synthesis / 296
Umpolung Synthons / 302
Acetylide Nucleophiles / 305
Ring Construction / 306
Robinson Annulation / 310
Diels–Alder Reaction / 312
HOMO–LUMO Interactions / 313
Stereoelectronic Factors / 316
1,3-Dipolar Cycloadditions / 319
Bibliography / 323
Problems / 324

11 Structure Determination of Organic Compounds 332

Structure Determination / 332

Chromatographic Purification / 333
Instrumental Methods / 335
Nuclear Magnetic Resonance / 336
Chemical Shift / 338
Spin–Spin Coupling / 344
Descriptions of Spin Systems / 350
 CONTENTS xi

Second-Order Splitting / 354

Structure Identification by 1 H NMR / 355
Carbon-13 NMR / 360
Infrared Spectroscopy / 366
IR Stretching Frequencies / 367
Use of IR Spectroscopy for Structure Determination / 371
Mass Spectrometry / 377
Fragmentation Processes / 384
Bibliography / 388
Problems / 388

Solutions to Chapter Problems 395

Index 471
 PREFACE

In keeping with a mechanistic emphasis, the book was reorganized. The chapter
on mechanism is now Chapter 5 instead of Chapter 10. Thus the first six chapters
focus on the mechanistic and structural underpinnings of organic chemistry.
Synthetic aspects of organic chemistry are then discussed from a mechanistic
and structural point of view. Several new sections have been added and oth-
ers expanded. An expanded discussion of resonance and aromaticity is found
in Chapter 1. A section on organopalladium chemistry and olefin metathesis has
been added to Chapter 8 as they relate to current methods of carbon–carbon bond
formation. Chapter 9 on free-radical reactions for carbon–carbon bond formation
has been revised. The discussion of Diels–Alder chemistry has been moved to
Chapter 10 and expanded. A number of new problems have been added which
serve to further illustrate the principles developed in each chapter. Finally, thanks
to input from many people who have read this text and taught from it, the dis-
cussion has been further honed and errors corrected.
What has evolved is a greater initial emphasis of the mechanistic and struc-
tural approach to organic chemistry. The application of these principles in a
discussion of modern synthetic methodology (functional group manipulation,
carbon–carbon bond formation, retrosynthetic analysis) provides a new orga-
nizational framework for understanding many of the most common and most
important synthetic reactions.
What has not changed is the premise that this text is meant to provide the tools
students need to master the material in advanced courses or compete successfully
in the workplace.

ROBERT V. HOFFMAN

xiii
 PREFACE TO THE
FIRST EDITION

This text was inspired by two observations. The first is that many entering grad-
uate students took organic chemistry as sophomores but since that time have had
little exposure to organic chemistry in a formal sense. Because of this time lapse
in their organic preparation, they often have difficulty performing well when
placed directly into mainstream graduate level organic courses. What is much
more effective is to first place them in a course which will bring them back
up to speed in basic organic chemistry and at the same time introduce many of
the advanced topics which are crucial to understanding current advances in the
field. A course well suited for this purpose is a one-semester, advanced organic
course at the senior undergraduate/beginning graduate level. Most departments,
including ours, have such a course in place. Textbook selection for this course is
problematic, however. If one of the standard advanced texts is used, only a small
part is actually covered and students are not prepared to master the complexities,
whereas if an undergraduate text is used, it often fails to push the students to
the next level. Consequently, there is a real need for a one-semester text which
gives a review of basic principles in addition to an exposure to the ideas which
are currently of great importance in organic chemistry. This text was written to
fill this need.
A second observation instrumental in shaping the approach of this text was
made during group discussions of the organic faculty and students. One common
exercise is to present practice cumulative exam problems to the group and discuss
ways in which they might be solved. It is very common for the students to
analyze the question in terms of reactions and transformations and try to arrive
at a solution based on the question as written. On the other hand, it is very
common for the faculty to ask very simple questions first—for example, “What
is the oxidation change?” “What is the pKa of the acid and what is the base?” and
“What stereochemical changes occur?” It is clear that more experienced organic
chemists begin from a very basic point of view and progress to a more complex
solution, whereas novice organic chemists tend to jump in at a much more difficult
level. It thus appears very important to initially emphasize the basic principles on
which organic chemistry depends and then progress to more specialized topics, all
the while emphasizing their relationship to the basic principles. This text utilizes
this organizational approach.
xv
xvi PREFACE TO THE FIRST EDITION

The result is a textbook designed for a one-semester advanced organic chem-

istry course. First and foremost it is a textbook and not a reference text. There
is plenty of material to fill a semester, but it is not comprehensive in its cov-
erage. Topics were chosen to provide a basic and well-rounded discussion of
ideas important in modern organic chemistry and to provide students with the
necessary tools to succeed in more specialized advanced courses. It is a book
to be taught from; thus instructors should take the opportunity to include spe-
cial or favorite topics at appropriate points. References to alternative textbook
and literature reviews of the subjects are included so that students can go to the
library and get a different explanation. This is important for encouraging students
to do library work as a means to independently gain insight and understanding.
Finally, there are abundant problems included at the end of each chapter so that
students can practice applying what they are learning. Working problems is the
single most effective way to learn and organize the large amount of information
that is encountered in organic chemistry, so there are a large number of practice
problems available at all levels of difficulty.
The goal of this text is to provide senior undergraduate students the organic
background required to move on successfully in their careers. For beginning
graduate students lacking this background, it provides a succinct yet rigorous
preparation for advanced organic courses.

R.V.H.
 1
FUNCTIONAL GROUPS AND
CHEMICAL BONDING

Functional Groups 1
Orbitals 5
Bonding Schemes 7
Antibonding Orbitals 13
Resonance 18
Conjugated π Systems 21
Aromaticity 23
Bibliography 26
Problems 27

FUNCTIONAL GROUPS

There are over 12 million known compounds of which more than 80% are organic
compounds. To make sense out of the nearly 9 million organic compounds and be
able to manipulate them and make new compounds, there must be some system
of organization whereby organic compounds can be categorized by a particular
property or group of properties. A natural method utilized by early practitioners
was to group organic compounds by the reactions that they underwent. Thus there
developed a whole variety of qualitative tests called classification tests which

Organic Chemistry: An Intermediate Text, Second Edition, by Robert V. Hoffman

ISBN 0-471-45024-3 Copyright  2004 John Wiley & Sons, Inc.

1
2 FUNCTIONAL GROUPS AND CHEMICAL BONDING

could be used to systematically categorize the reactivity of a compound and thus

allow it to be grouped with others of similar chemical reactivity. These tests are
still very useful to practicing organic chemists and collectively are known as
organic qualitative analysis.
Classification tests are used to distinguish organic compounds and segregate
them into different functional classes based on their chemical properties. Orig-
inally a group of compounds that showed similar chemical behavior based on
the classification tests were named for a property or behavior (e.g., acids from
acer meaning “sour,” aromatic compounds from their odors). With the evolu-
tion of the science of chemistry and the development of more modern views
of atoms and molecules, a different definition of functional classes is possi-
ble. The behavior of organic compounds is now organized into patterns that are
based on recurrent groups of atoms—functional groups. The sites in molecules
at which chemical reactions occur are localized at the functional groups in the
molecule; the rest of the molecule is the same after the reaction as before.
Thus, instead of thinking of the whole molecule in terms of its chemical reac-
tivity, it is only necessary to recognize what functional group or groups are
present in the molecule. It is then possible to predict the chemical behavior
of the molecule based on the known chemistry of the functional groups that
it contains.
This turns out to be a huge simplification. Since the numbers of functional
groups are relatively small, it is possible to classify a very large number of
individual compounds by a relatively small number of functional groups. So
the first step to enlightenment in organic chemistry is to realize the key role
that functional groups play in simplifying the subject, and the second step is
to learn the functional groups by name, structure, and formula. While a great
number of them may have already been encountered in the introductory organic
course, it is helpful to review them. Table 1.1 is a list of the most common
functional groups. While there are quite a few other functional groups that are
not shown, those found in Table 1.1 are the most common and are present in
the vast majority of organic compounds. Notice that not all functional groups
contain only carbon atoms (e.g., the nitro group and the carbodiimide groups),
and some functional groups differ at atoms other than carbon (compare the nitro
and nitroso groups and the sulfoxide and sulfone groups). Since functional groups
are reference points for predicting and understanding the reactions of individual
organic molecules, it is very important to be able to recognize these functional
groups (and others that might be encountered in the future). It is also useful to
learn normal structural abbreviations that are used to indicate functional groups
that are present in chemical structures. The abbreviations in Table 1.2 correspond
to the groups that are shown in Table 1.1.
A major reason that the behavior of organic compounds can be generalized
in terms of the functional groups they contain is because the bonds holding a
given functional group together are the same regardless of the compound which
contains that functional group. The four compounds shown below all contain the
carboxylic acid functional group, which is highlighted within the boxes. Thus all
Other documents randomly have
different content
there, it is not to be doubted, is a Church of God; for his promise
can never deceive—“where two or three are gathered together in my
name, there am I in the midst of them.”[741] But, that we may have a
clear understanding of the whole of this subject, let us proceed by
the following steps: That the universal Church is the whole
multitude, collected from all nations, who, though dispersed in
countries widely distant from each other, nevertheless consent to the
same truth of Divine doctrine, and are united by the bond of the
same religion; that in this universal Church are comprehended
particular churches, distributed according to human necessity in
various towns and villages; and that each of these respectively is
justly distinguished by the name and authority of a church; and that
individuals, who, on a profession of piety, are enrolled among
Churches of the same description, though they are really strangers
to any particular Church, do nevertheless in some respect belong to
it, till they are expelled from it by a public decision. There is some
difference, however, in the mode of judging respecting private
persons and churches. For it may happen, in the case of persons
whom we think altogether unworthy of the society of the pious, that,
on account of the common consent of the Church, by which they are
tolerated in the body of Christ, we may be obliged to treat them as
brethren, and to class them in the number of believers. In our
private opinion we approve not of such persons as members of the
Church, but we leave them the station they hold among the people
of God, till it be taken away from them by legitimate authority. But
respecting the congregation itself, we must form a different
judgment. If they possess and honour the ministry of the word, and
the administration of the sacraments, they are, without all doubt,
entitled to be considered as a Church; because it is certain that the
word and sacraments cannot be unattended with some good effects.
In this manner, we preserve the unity of the universal Church, which
diabolical spirits have always been endeavouring to destroy; and at
the same time without interfering with the authority of those
legitimate assemblies, which local convenience has distributed in
different places.
X. We have stated that the marks by which the Church is to be
distinguished, are, the preaching of the word and the administration
of the sacraments. For these can nowhere exist without bringing
forth fruit, and being prospered with the blessing of God. I assert
not that wherever the word is preached, the good effects of it
immediately appear; but that it is never received so as to obtain a
permanent establishment, without displaying some efficacy. However
this may be, where the word is heard with reverence, and the
sacraments are not neglected, there we discover, while that is the
case, an appearance of the Church, which is liable to no suspicion of
uncertainty, of which no one can safely despise the authority, or
reject the admonitions, or resist the counsels, or slight the censures,
much less separate from it and break up its unity. For so highly does
the Lord esteem the communion of his Church, that he considers
every one as a traitor and apostate from religion, who perversely
withdraws himself from any Christian society which preserves the
true ministry of the word and sacraments. He commends the
authority of the Church, in such a manner as to account every
violation of it an infringement of his own. For it is not a trivial
circumstance, that the Church is called “the house of God, the pillar
and ground of truth.”[742] For in these words Paul signifies that in
order to keep the truth of God from being lost in the world, the
Church is its faithful guardian; because it has been the will of God,
by the ministry of the Church, to preserve the pure preaching of his
word, and to manifest himself as our affectionate Father, while he
nourishes us with spiritual food, and provides all things conducive to
our salvation. Nor is it small praise, that the Church is chosen and
separated by Christ to be his spouse, “not having spot or
wrinkle,”[743] to be “his body, the fulness of him that filleth all in
all.”[744] Hence it follows, that a departure from the Church is a
renunciation of God and Christ. And such a criminal dissension is so
much the more to be avoided, because, while we endeavour, as far
as lies in our power, to destroy the truth of God, we deserve to be
crushed with the most powerful thunders of his wrath. Nor is it
possible to imagine a more atrocious crime, than that sacrilegious
perfidy, which violates the conjugal relation that the only begotten
Son of God has condescended to form with us.
XI. Let us, therefore, diligently retain those characters impressed
upon our minds, and estimate them according to the judgment of
God. For there is nothing that Satan labours more to accomplish,
than to remove and destroy one or both of them; at one time to
efface and obliterate these marks, and so to take away all true and
genuine distinction of the Church; at another to inspire us with
contempt of them, and so to drive us out of the Church by an open
separation. By his subtlety it has happened, that in some ages the
pure preaching of the word has altogether disappeared; and in the
present day he is labouring with the same malignity to overturn the
ministry; which, however, Christ has ordained in his Church, so that
if it were taken away, the edification of the Church would be quite at
an end. How dangerous, then, how fatal is the temptation, when it
even enters into the heart of a man to withdraw himself from that
congregation, in which he discovers those signs and characters
which the Lord has deemed sufficiently descriptive of his Church! We
see, however, that great caution requires to be observed on both
sides. For, to prevent imposture from deceiving us, under the name
of the Church, every congregation assuming this name should be
brought to that proof, like gold to the touchstone. If it have the
order prescribed by the Lord in the word and sacraments, it will not
deceive us; we may securely render to it the honour due to all
churches. On the contrary, if it pretend to the name of a Church,
without the word and sacraments, we ought to beware of such
delusive pretensions, with as much caution as, in the other case, we
should use in avoiding presumption and pride.
XII. When we affirm the pure ministry of the word, and pure order in
the celebration of the sacraments, to be a sufficient pledge and
earnest, that we may safely embrace the society in which both these
are found, as a true Church, we carry the observation to this point,
that such a society should never be rejected as long as it continues
in those things, although in other respects it may be chargeable with
many faults. It is possible, moreover, that some fault may insinuate
itself into the preaching of the doctrine, or the administration of the
sacraments, which ought not to alienate us from its communion. For
all the articles of true doctrine are not of the same description. Some
are so necessary to be known, that they ought to be universally
received as fixed and indubitable principles, as the peculiar maxims
of religion; such as, that there is one God; that Christ is God and the
Son of God; that our salvation depends on the mercy of God; and
the like. There are others, which are controverted among the
churches, yet without destroying the unity of the faith. For why
should there be a division on this point, if one church be of opinion,
that souls, at their departure from their bodies, are immediately
removed to heaven; and another church venture to determine
nothing respecting their local situation, but be nevertheless firmly
convinced, that they live to the Lord; and if this diversity of
sentiment on both sides be free from all fondness for contention and
obstinacy of assertion? The language of the apostle is, “Let us
therefore, as many as be perfect, be thus minded; and if in any
thing ye be otherwise minded, God shall reveal even this unto
you.”[745] Does not this sufficiently show, that a diversity of opinion
respecting these nonessential points ought not to be a cause of
discord among Christians? It is of importance, indeed, that we
should agree in every thing; but as there is no person who is not
enveloped with some cloud of ignorance, either we must allow of no
church at all, or we must forgive mistakes in those things, of which
persons may be ignorant, without violating the essence of religion,
or incurring the loss of salvation. Here I would not be understood to
plead for any errors, even the smallest, or to recommend their being
encouraged by connivance or flattery. But I maintain, that we ought
not, on account of every trivial difference of sentiment, to abandon
the Church, which retains the saving and pure doctrine that insures
the preservation of piety, and supports the use of the sacraments
instituted by our Lord. In the mean time, if we endeavour to correct
what we disapprove, we are acting in this case according to our
duty. And to this we are encouraged by the direction of Paul: “If any
thing be revealed to another that sitteth by, let the first hold his
peace.”[746] From which it appears, that every member of the Church
is required to exert himself for the general edification, according to
the measure of his grace, provided he do it decently and in order;
that is to say, that we should neither forsake the communion of the
Church, nor, by continuing in it, disturb its peace and well regulated
discipline.
XIII. But in bearing with imperfections of life, we ought to carry our
indulgence a great deal further. For this is a point in which we are
very liable to err, and here Satan lies in wait to deceive us with no
common devices. For there have always been persons, who, from a
false notion of perfect sanctity, as if they were already become
disembodied spirits, despised the society of all men in whom they
could discover any remains of human infirmity. Such, in ancient
times, were the Cathari, and also the Donatists, who approached to
the same folly. Such, in the present day, are some of the
Anabaptists, who would be thought to have made advances in piety
beyond all others. There are others who err, more from an
inconsiderate zeal for righteousness, than from this unreasonable
pride. For when they perceive, that among those to whom the
gospel is preached, its doctrine is not followed by correspondent
effects in the life, they immediately pronounce, that there no church
exists. This is, indeed, a very just ground of offence, and one for
which we furnish more than sufficient occasion in the present
unhappy age; nor is it possible to excuse our abominable inactivity,
which the Lord will not suffer to escape with impunity, and which he
has already begun to chastise with heavy scourges. Woe to us,
therefore, who, by the dissolute licentiousness of our crimes, cause
weak consciences to be wounded on our account! But, on the other
hand, the error of the persons of whom we now speak, consists in
not knowing how to fix any limits to their offence. For where our
Lord requires the exercise of mercy, they entirely neglect it, and
indulge themselves in immoderate severity. Supposing it impossible
for the Church to exist, where there is not a perfect purity and
integrity of life, through a hatred of crimes they depart from the true
Church, while they imagine themselves to be only withdrawing from
the factions of the wicked. They allege, that the Church of Christ is
holy. But that they may also understand, that it is composed of good
and bad men mingled together, let them hear that parable from the
lips of Christ, where it is compared to a net, in which fishes of all
kinds are collected, and no separation is made till they are exposed
on the shore.[747] Let them hear another parable, comparing the
Church to a field, which, after having been sown with good seed, is,
by the craft of an enemy, corrupted with tares, from which it is never
cleared till the harvest is brought into the barn.[748] Lastly, let them
hear another comparison of the Church to a threshing-floor, in which
the wheat is collected in such a manner, that it lies concealed under
the chaff, till, after being carefully purged, by winnowing and sifting,
it is at length laid up in the garner.[749] But if our Lord declares, that
the Church is to labour under this evil, and to be encumbered with a
mixture of wicked men, even till the day of judgment, it is vain to
seek for a Church free from every spot.
XIV. But they exclaim, that it is an intolerable thing that the
pestilence of crimes so generally prevails. I grant it would be happy
if the fact were otherwise; but in reply, I would present them with
the judgment of the apostle. Among the Corinthians, more than a
few had gone astray, and the infection had seized almost the whole
society; there was not only one species of sin, but many; and they
were not trivial faults, but dreadful crimes; and there was not only a
corruption of morals, but also of doctrine. In this case, what is the
conduct of the holy apostle, the organ of the heavenly Spirit, by
whose testimony the Church stands or falls? Does he seek to
separate from them? Does he reject them from the kingdom of
Christ? Does he strike them with the thunderbolt of the severest
anathema? He not only does none of these things, but, on the
contrary, acknowledges and speaks of them as a Church of Christ
and a society of saints. If there remained a church among the
Corinthians, where contentions, factions, and emulations were
raging; where cupidity, disputes, and litigations were prevailing;
where a crime held in execration even among the Gentiles, was
publicly sanctioned; where the name of Paul, whom they ought to
have revered as their father, was insolently defamed; where some
ridiculed the doctrine of the resurrection, with the subversion of
which the whole gospel would be annihilated; where the graces of
God were made subservient to ambition, instead of charity; where
many things were conducted without decency and order;[750] and if
there still remained a Church, because the ministry of the word and
sacraments was not rejected—who can refuse the name of a Church
to those who cannot be charged with a tenth part of those crimes?
And those who display such violence and severity against the
Churches of the present age, I ask, how would they have conducted
themselves towards the Galatians, who almost entirely deserted the
gospel, but among whom, nevertheless, the same apostle found
Churches?[751]
XV. They object that Paul bitterly reproves the Corinthians for
admitting an atrocious offender into their company, and follows this
reproof with a general declaration, that with a man of scandalous life
it is not lawful even to eat.[752] Here they exclaim, If it be not lawful
to eat common bread with him, how can it be lawful to unite with
him in eating the bread of the Lord? I confess it is a great disgrace,
if persons of immoral lives occupy places among the children of God;
and if the sacred body of Christ be prostituted to them, the disgrace
is vastly increased. And, indeed, if Churches be well regulated, they
will not suffer persons of abandoned characters among them, nor
will they promiscuously admit the worthy and the unworthy to that
sacred supper. But because the pastors are not always so diligent in
watching over them, and sometimes exercise more indulgence than
they ought, or are prevented from exerting the severity they would
wish, it happens that even those who are openly wicked are not
always expelled from the society of the saints. This I acknowledge to
be a fault, nor have I any inclination to extenuate it, since Paul
sharply reproves it in the Corinthians. But though the Church may be
deficient in its duty, it does not therefore follow that it is the place of
every individual to pass judgment of separation for himself. I admit
that it is the duty of a pious man to withdraw himself from all private
intimacy with the wicked, and not to involve himself in any voluntary
connection with them. But it is one thing to avoid familiar
intercourse with the wicked; and another thing, from hatred of
them, to renounce the communion of the Church. And persons who
deem it sacrilege to participate with them the bread of the Lord, are
in this respect far more rigid than Paul. For when he exhorts us to a
pure and holy participation of it, he requires not one to examine
another, or every one to examine the whole Church, but each
individual to prove himself. If it were unlawful to communicate with
an unworthy person, Paul would certainly have enjoined us to look
around us, to see whether there were not some one in the multitude
by whose impurity we might be contaminated. But as he only
requires every one to examine himself, he shows that it is not the
least injury to us if some unworthy persons intrude themselves with
us. And this is fully implied in what he afterwards subjoins: “He that
eateth and drinketh unworthily, eateth and drinketh judgment to
himself.”[753] He says, not to others, but to himself, and with
sufficient reason. For it ought not to be left to the judgment of every
individual who ought to be admitted into the Church, and who ought
to be expelled from it. This authority belongs to the whole Church,
and cannot be exercised without legitimate order, as will be stated
more at large hereafter. It would be unjust, therefore, that any
individual should be contaminated with the unworthiness of another,
whose approach it is neither in his power nor his duty to prevent.
XVI. But though this temptation sometimes arises even to good
men, from an inconsiderate zeal for righteousness, yet we shall
generally find that excessive severity is more owing to pride and
haughtiness, and a false opinion which persons entertain of their
own superior sanctity, than to true holiness, and a real concern for
its interests. Those, therefore, who are most daring in promoting a
separation from the Church, and act, as it were, as standard-bearers
in the revolt, have in general no other motive than to make an
ostentatious display of their own superior excellence, and their
contempt of all others. Augustine correctly and judiciously observes
—“Whereas the pious rule and method of ecclesiastical discipline
ought principally to regard the unity of the Spirit in the bond of
peace, which the apostle enjoined to be preserved by mutual
forbearance, and which not being preserved, the medicinal
punishment is evinced to be not only superfluous, but even
pernicious, and therefore to be no longer medicinal; those wicked
children, who, not from a hatred of the iniquities of others, but from
a fondness for their own contentions, earnestly endeavour to draw
the simple and uninformed multitude wholly after them, by
entangling them with boasting of their own characters, or at least to
divide them; those persons, I say, inflated with pride, infuriated with
obstinacy, insidious in the circulation of calumnies, and turbulent in
raising seditions, conceal themselves under the mask of a rigid
severity, lest they should be proved to be destitute of the truth; and
those things which in the Holy Scriptures are commanded to be
done with great moderation, and without violating the sincerity of
love, or breaking the unity of peace, for the correction of the faults
of our brethren, they pervert to the sacrilege of schism, and an
occasion of separation from the Church.” To pious and peaceable
persons he gives this advice: that they should correct in mercy
whatever they can; that what they cannot, they should patiently
bear, and affectionately lament, till God either reform and correct it,
or, at the harvest, root up the tares and sift out the chaff. All pious
persons should study to fortify themselves with these counsels, lest,
while they consider themselves as valiant and strenuous defenders
of righteousness, they depart from the kingdom of heaven, which is
the only kingdom of righteousness. For since it is the will of God that
the communion of his Church should be maintained in this external
society, those who, from an aversion to wicked men, destroy the
token of that society, enter on a course in which they are in great
danger of falling from the communion of saints. Let them consider,
in the first place, that in a great multitude there are many who
escape their observation, who, nevertheless, are truly holy and
innocent in the sight of God. Secondly, let them consider, that of
those who appear subject to moral maladies, there are many who by
no means please or flatter themselves in their vices, but are
oftentimes aroused, with a serious fear of God, to aspire to greater
integrity. Thirdly, let them consider that judgment ought not to be
pronounced upon a man from a single act, since the holiest persons
have sometimes most grievous falls. Fourthly, let them consider, that
the ministry of the word, and the participation of the sacraments,
have too much influence in preserving the unity of the Church, to
admit of its being destroyed by the guilt of a few impious men.
Lastly, let them consider, that in forming an estimate of the Church,
the judgment of God is of more weight than that of man.
XVII. When they allege that there must be some reason why the
Church is said to be holy, it is necessary to examine the holiness in
which it excels; lest by refusing to admit the existence of a Church
without absolute and sinless perfection, we should leave no Church
in the world. It is true, that, as Paul tells us, “Christ loved the
Church, and gave himself for it, that he might sanctify and cleanse
it, by the washing of water by the word, that he might present it to
himself a glorious Church, not having spot, or wrinkle, or any such
thing.”[754] It is nevertheless equally true, that the Lord works from
day to day in smoothing its wrinkles, and purging away its spots;
whence it follows, that its holiness is not yet perfect. The Church,
therefore, is so far holy, that it is daily improving, but has not yet
arrived at perfection; that it is daily advancing, but has not yet
reached the mark of holiness; as in another part of this work will be
more fully explained. The predictions of the prophets, therefore, that
“Jerusalem shall be holy, and there shall no strangers pass through
her any more,” and that the way of God shall be a “way of holiness,
over which the unclean shall not pass,”[755] are not to be understood
as if there were no blemish remaining in any of the members of the
Church; but because they aspire with all their souls towards perfect
holiness and purity, the goodness of God attributes to them that
sanctity to which they have not yet fully attained. And though such
evidences of sanctification are oftentimes rarely to be found among
men, yet it must be maintained, that, from the foundation of the
world, there has never been a period in which God had not his
Church in it; and that, to the consummation of all things, there
never will be a time in which he will not have his Church. For
although, in the very beginning of time, the whole human race was
corrupted and defiled by the sin of Adam; yet, from this polluted
mass, God always sanctifies some vessels to honour, so that there is
no age which has not experienced his mercy. This he has testified by
certain promises, such as the following: “I have made a covenant
with my chosen: I have sworn unto David, my servant, Thy seed will
I establish for ever, and build up thy throne to all generations.”[756]
Again: “The Lord hath chosen Zion; he hath desired it for his
habitation. This is my rest for ever.”[757] Again: “Thus saith the Lord,
which giveth the sun for a light by day, and the ordinances of the
moon and of the stars for a light by night: If those ordinances
depart from before me, saith the Lord, then the seed of Israel also
shall cease from being a nation before me for ever.”[758]
XVIII. Of this truth Christ himself, the apostles, and almost all the
prophets, have given us an example. Dreadful are those descriptions
in which Isaiah, Jeremiah, Joel, Habakkuk, and others, deplore the
disorders of the Church of Jerusalem. There was such general and
extreme corruption in the people, in the magistrates, and in the
priests, that Isaiah does not hesitate to compare Jerusalem to
Sodom and Gomorrah. Religion was partly despised, partly
corrupted. Their manners were generally disgraced by thefts,
robberies, treacheries, murders, and similar crimes. Nevertheless,
the prophets on this account neither raised themselves new
churches, nor built new altars for the oblation of separate sacrifices;
but whatever were the characters of the people, yet because they
considered that God had deposited his word among that nation, and
instituted the ceremonies in which he was there worshipped, they
lifted up pure hands to him even in the congregation of the impious.
If they had thought that they contracted any contagion from these
services, surely they would have suffered a hundred deaths rather
than have permitted themselves to be dragged to them. There was
nothing therefore to prevent their departure from them, but the
desire of preserving the unity of the Church. But if the holy prophets
were restrained by a sense of duty from forsaking the Church on
account of the numerous and enormous crimes which were
practised, not by a few individuals, but almost by the whole nation,
—it is extreme arrogance in us, if we presume immediately to
withdraw from the communion of a Church where the conduct of all
the members is not compatible either with our judgment, or even
with the Christian profession.
XIX. Now, what kind of an age was that of Christ and his apostles?
Yet the desperate impiety of the Pharisees, and the dissolute lives
every where led by the people, could not prevent them from using
the same sacrifices, and assembling in the same temple with others,
for the public exercises of religion. How did this happen, but from a
knowledge that the society of the wicked could not contaminate
those who with pure consciences united with them in the same
solemnities? If any one pay no deference to the prophets and
apostles, let him at least acquiesce in the authority of Christ. Cyprian
has excellently remarked, “Although tares, or impure vessels, are
found in the Church, yet this is not a reason why we should
withdraw from it. It only behoves us to labour that we may be the
wheat, and to use our utmost endeavours and exertions, that we
may be vessels of gold or of silver. But to break in pieces the vessels
of earth belongs to the Lord alone, to whom a rod of iron is also
given. Nor let any one arrogate to himself what is exclusively the
province of the Son of God, by pretending to fan the floor, clear
away the chaff, and separate all the tares by the judgment of man.
This is proud obstinacy and sacrilegious presumption, originating in a
corrupt frenzy.” Let these two points, then, be considered as
decided; first, that he who voluntarily deserts the external
communion of the Church where the word of God is preached, and
the sacraments are administered, is without any excuse; secondly,
that the faults either of few persons or of many, form no obstacles to
a due profession of our faith in the use of the ceremonies instituted
by God; because the pious conscience is not wounded by the
unworthiness of any other individual, whether he be a pastor or a
private person; nor are the mysteries less pure and salutary to a
holy and upright man, because they are received at the same time
by the impure.
XX. Their severity and haughtiness go to still greater lengths.
Acknowledging no church but such as is pure from the smallest
blemishes, they are even angry with honest teachers, because, by
exhorting believers to progressive improvements, they teach them to
groan under the burden of sins, and to seek for pardon all their
lifetime. For hereby, they pretend, the people are drawn away from
perfection. I confess, that in urging men to perfection, we ought to
labour with unremitting ardour and diligence; but to inspire their
minds with a persuasion that they have already attained it, while
they are yet in the pursuit of it, I maintain to be a diabolical
invention. Therefore, in the Creed, the communion of saints is
immediately followed by the forgiveness of sins, which can only be
obtained by the citizens and members of the Church, as we read in
the prophet.[759] The heavenly Jerusalem, therefore, ought first to be
built, in which this favour of God may be enjoyed, that whoever shall
enter it, their iniquity shall be blotted out. Now, I affirm that this
ought first to be built; not that there can ever be any Church without
remission of sins, but because God has not promised to impart his
mercy, except in the communion of saints. Our first entrance,
therefore, into the Church and kingdom of God, is the remission of
sins, without which we have no covenant or union with God. For
thus he speaks by the prophet: “In that day will I make a covenant
for them with the beasts of the field, and with the fowls of heaven,
and with the creeping things of the ground; and I will break the bow
and the sword, and the battle out of the earth, and will make them
to lie down safely. And I will betroth thee unto me for ever; yea, I
will betroth thee unto me in righteousness, and in judgment, and in
loving-kindness, and in mercies.”[760] We see how God reconciles us
to himself by his mercy. So in another place, where he foretells the
restoration of the people whom he had scattered in his wrath, he
says, “I will cleanse them from all their iniquity, whereby they have
sinned against me.”[761] Wherefore it is by the sign of ablution, that
we are initiated into the society of his Church; by which we are
taught that there is no admittance for us into the family of God,
unless our pollution be first taken away by his goodness.
XXI. Nor does God only once receive and adopt us into his Church by
the remission of sins; he likewise preserves and keeps us in it by the
same mercy. For to what purpose would it be, if we obtained a
pardon which would afterwards be of no use? And that the mercy of
the Lord would be vain and delusive, if it were only granted for once,
all pious persons can testify to themselves; for every one of them is
all his lifetime conscious of many infirmities, which need the Divine
mercy. And surely it is not without reason, that God particularly
promises this grace to the members of his family, and commands the
same message of reconciliation to be daily addressed to them. As we
carry about with us the relics of sin, therefore, as long as we live, we
shall scarcely continue in the Church for a single moment, unless we
are sustained by the constant grace of the Lord in forgiving our sins.
But the Lord has called his people to eternal salvation; they ought,
therefore, to believe that his grace is always ready to pardon their
sins. Wherefore it ought to be held as a certain conclusion, that from
the Divine liberality, by the intervention of the merit of Christ,
through the sanctification of the Spirit, pardon of sins has been, and
is daily, bestowed upon us, who have been admitted and ingrafted
into the body of the Church.
XXII. It was to dispense this blessing to us, that the keys were given
to the Church.[762] For, when Christ gave commandment to his
apostles, and conferred on them the power of remitting sins,[763] it
was not with an intention that they should merely absolve from their
sins those who were converted from impiety to the Christian faith,
but rather that they should continually exercise this office among the
faithful. This is taught by Paul, when he says, that the message of
reconciliation was committed to the ministers of the Church, that in
the name of Christ they might daily exhort the people to be
reconciled to God.[764] In the communion of saints, therefore, sins
are continually remitted to us by the ministry of the Church, when
the presbyters or bishops, to whom this office is committed, confirm
pious consciences, by the promises of the gospel, in the hope of
pardon and remission; and that as well publicly as privately,
according as necessity requires. For there are many persons who, on
account of their infirmity, stand in need of separate and private
consolation. And Paul tells us that he “taught,” not only publicly, but
also “from house to house, testifying repentance toward God, and
faith toward our Lord Jesus Christ;”[765] and admonished every
individual separately respecting the doctrine of salvation. Here are
three things, therefore, worthy of our observation. First, that
whatever holiness may distinguish the children of God, yet such is
their condition as long as they inhabit a mortal body, that they
cannot stand before God without remission of sins. Secondly, that
this benefit belongs to the Church; so that we cannot enjoy it unless
we continue in its communion. Thirdly, that it is dispensed to us by
the ministers and pastors of the Church, either in the preaching of
the gospel, or in the administration of the sacraments; and that this
is the principal exercise of the power of the keys, which the Lord has
conferred on the society of believers. Let every one of us, therefore,
consider it as his duty, not to seek remission of sins any where but
where the Lord has placed it. Of public reconciliation, which is a
branch of discipline, we shall speak in its proper place.
XXIII. But as those fanatic spirits, of whom I spoke, endeavour to
rob the Church of this sole anchor of salvation, our consciences
ought to be still more strongly fortified against such a pestilent
opinion. The Novatians disturbed the ancient Churches with this
tenet; but the present age also has witnessed some of the
Anabaptists, who resemble the Novatians by falling into the same
follies. For they imagine that by baptism the people of God are
regenerated to a pure and angelic life, which cannot be
contaminated by any impurities of the flesh. And if any one be guilty
of sin after baptism, they leave him no prospect of escaping the
inexorable judgment of God. In short, they encourage no hope of
pardon in any one who sins after having received the grace of God;
because they acknowledge no other remission of sins than that by
which we are first regenerated. Now, though there is no falsehood
more clearly refuted in the Scripture than this, yet because its
advocates find persons to submit to their impositions, as Novatus
formerly had numerous followers, let us briefly show how very
pernicious their error is both to themselves and to others. In the first
place, when the saints obey the command of the Lord by a daily
repetition of this prayer, “forgive us our debts,”[766] they certainly
confess themselves to be sinners. Nor do they pray in vain, for our
Lord has not enjoined the use of any petitions, but such as he
designed to grant. And after he had declared that the whole prayer
would be heard by the Father, he confirmed this absolution by a
special promise. What do we want more? The Lord requires from the
saints a confession of sins, and that daily as long as they live, and
he promises them pardon. What presumption is it either to assert
that they are exempt from sin, or, if they have fallen, to exclude
them from all grace! To whom does he enjoin us to grant forgiveness
seventy times seven times? Is it not to our brethren? And what was
the design of this injunction, but that we might imitate his
clemency? He pardons, therefore, not once or twice, but as often as
the sinner is alarmed with a sense of his sins, and sighs for mercy.
XXIV. But to begin from the infancy of the Church: the patriarchs
had been circumcised, admitted to the privileges of the covenant,
and without doubt instructed in justice and integrity by the care of
their father, when they conspired to murder their brother. This was a
crime to be abominated even by the most desperate and abandoned
robbers. At length, softened by the admonitions of Judah, they sold
him for a slave. This also was an intolerable cruelty. Simon and Levi,
in a spirit of nefarious revenge, condemned even by the judgment of
their father, murdered the inhabitants of Sichem. Reuben was guilty
of execrable incest with his father’s concubine. Judah, with an
intention of indulging a libidinous passion, violated the law of nature
by a criminal connection with his son’s wife. Yet they are so far from
being expunged out of the number of the chosen people, that, on
the contrary, they are constituted the heads of the nation.[767] What
shall we say of David? Though he was the official guardian of
justice, how scandalously did he prepare the way for the gratification
of a blind passion, by the effusion of innocent blood! He had already
been regenerated, and among the regenerate had been
distinguished by the peculiar commendations of the Lord; yet he
perpetrated a crime even among heathens regarded with horror, and
yet he obtained mercy.[768] And not to dwell any longer on particular
examples, the numerous promises which the law and the prophets
contain, of Divine mercy towards the Israelites, are so many proofs
of the manifestation of God’s placability to the offences of his
people. For what does Moses promise to the people in case of their
return to the Lord, after having fallen into idolatry? “Then the Lord
thy God will turn thy captivity, and have compassion upon thee, and
will return and gather thee from all the nations, whither the Lord thy
God hath scattered thee. If any of thine be driven out unto the
outmost parts of heaven, from thence will the Lord thy God gather
thee.”[769]
XXV. But I am unwilling to commence an enumeration which would
have no end. For the prophets are full of such promises, which offer
mercy to the people, though covered with innumerable crimes. What
sin is worse than rebellion? It is described as a divorce between God
and the Church: yet this is overcome by the goodness of God. Hear
his language by the mouth of Jeremiah: “If a man put away his wife,
and she go from him, and become another man’s, shall he return
unto her again? Shall not that land be greatly polluted? But thou
hast played the harlot with many lovers, and thou hast polluted the
land with thy whoredoms and with thy wickedness. Yet return again
to me, thou backsliding Israel, saith the Lord, and I will not cause
mine anger to fall upon you; for I am merciful, saith the Lord, and
will not keep anger for ever.”[770] And surely there cannot possibly be
any other disposition in him who affirms, that he “hath no pleasure
in the death of the wicked, but that the wicked turn from his way
and live.”[771] Therefore, when Solomon dedicated the temple, he
appointed it also for this purpose, that prayers, offered to obtain
pardon of sins, might there be heard and answered. His words are,
“If they sin against thee, (for there is no man that sinneth not,) and
thou be angry with them, and deliver them to the enemy, so that
they carry them away captives unto the land of the enemy, far or
near; yet if they shall bethink themselves, and repent in the land
whither they were carried captives, and repent and make
supplication unto thee in the land of those that carried them
captives, saying, We have sinned, and have done perversely, we
have committed wickedness; and pray unto thee toward the land
which thou gavest unto their fathers, the city which thou hast
chosen, and the house which I have built for thy name; then hear
thou their prayer and their supplication in heaven, and forgive thy
people that have sinned against thee, and all their transgressions
wherein they have transgressed against thee.”[772] Nor was it without
cause that in the law the Lord ordained daily sacrifices for sins; for
unless he had foreseen that his people would be subject to the
maladies of daily sins, he would never have appointed these
remedies.[773]
XXVI. Now, I ask whether, by the advent of Christ, in whom the
fulness of grace was displayed, believers have been deprived of this
benefit, so that they can no longer presume to supplicate for the
pardon of their sins; so that if they offend against the Lord, they can
obtain no mercy. What would this be but to affirm, that Christ came
for the destruction of his people, and not for their salvation; if the
loving-kindness of God, in the pardon of sins, which was continually
ready to be exercised to the saints under the Old Testament, be
maintained to be now entirely withdrawn? But if we give any credit
to the Scriptures, which proclaim that in Christ the grace and
philanthropy of God have at length been fully manifested, that his
mercy has been abundantly diffused, and reconciliation between God
and man accomplished,[774] we ought not to doubt that the clemency
of our heavenly Father is displayed to us in greater abundance,
rather than restricted or diminished. Examples to prove this are not
wanting. Peter, who had been warned that he who would not
confess the name of Christ before men would be denied by him
before angels, denied him three times in one night, and
accompanied the denial with execrations; yet he was not refused
pardon.[775] Those of the Thessalonians who led disorderly lives, are
reprehended by the apostle, in order to be invited to repentance.[776]
Nor does Peter drive Simon Magus himself to despair; but rather
directs him to cherish a favourable hope, when he persuades him to
pray for forgiveness.[777]
XXVII. What are we to say of cases in which the most enormous sins
have sometimes seized whole Churches? From this situation Paul
rather mercifully reclaimed them, than abandoned them to the
curse. The defection of the Galatians was no trivial offence.[778] The
Corinthians were still less excusable, their crimes being more
numerous and equally enormous.[779] Yet neither are excluded from
the mercy of the Lord: on the contrary, the very persons who had
gone beyond all others in impurity, unchastity, and fornication, are
expressly invited to repentance. For the covenant of the Lord will
ever remain eternal and inviolable, which he has made with Christ,
the antitype of Solomon, and with all his members, in these words:
“If his children forsake my law, and walk not in my judgments; if
they break my statutes, and keep not my commandments; then will
I visit their transgression with the rod, and their iniquity with stripes.
Nevertheless my loving-kindness will I not utterly take from him.”[780]
Finally, the order of the Creed teaches us that pardon of sins ever
continues in the Church of Christ, because, after having mentioned
the Church, it immediately adds the forgiveness of sins.
XXVIII. Some persons, who are a little more judicious, perceiving the
notion of Novatus to be so explicitly contradicted by the Scripture,
do not represent every sin as unpardonable, but only voluntary
transgression, into which a person may have fallen with the full
exercise of his knowledge and will. These persons admit of no
pardon for any sins, but such as may have been the mere errors of
ignorance. But as the Lord, in the law, commanded some sacrifices
to be offered to expiate the voluntary sins of believers, and others to
atone for sins of ignorance, what extreme presumption is it to deny
that there is any pardon for voluntary transgression! I maintain, that
there is nothing more evident, than that the one sacrifice of Christ is
available for the remission of the voluntary sins of the saints, since
the Lord has testified the same by the legal victims, as by so many
types. Besides, who can plead ignorance as an excuse for David,
who was evidently so well acquainted with the law? Did not David
know that adultery and murder were great crimes, which he daily
punished in others? Did the patriarchs consider fratricide as lawful?
Had the Corinthians learned so little that they could imagine
impurity, incontinence, fornication, animosities, and contentions, to
be pleasing to God? Could Peter, who had been so carefully warned,
be ignorant how great a crime it was to abjure his Master? Let us
not, therefore, by our cruelty, shut the gate of mercy which God has
so liberally opened.
XXIX. I am fully aware that the old writers have explained those
sins, which are daily forgiven to believers, to be the smaller faults,
which are inadvertently committed through the infirmity of the flesh;
but solemn repentance, which was then required for greater
offences, they thought, was no more to be repeated than baptism.
This sentiment is not to be understood as indicating their design,
either to drive into despair such persons as had relapsed after their
first repentance, or to extenuate those errors, as if they were small
in the sight of God. For they knew that the saints frequently stagger
through unbelief; that they sometimes utter unnecessary oaths; that
they occasionally swell into anger, and even break out into open
reproaches; and that they are likewise chargeable with other faults,
which the Lord holds in the greatest abomination. They expressed
themselves in this manner, to distinguish between private offences
and those public crimes which were attended with great scandal in
the Church. But the difficulty, which they made, of forgiving those
who had committed any thing deserving of ecclesiastical censure,
did not arise from an opinion that it was difficult for them to obtain
pardon from the Lord; they only intended by this severity to deter
others from rashly running into crimes, which would justly be
followed by their exclusion from the communion of the Church. The
word of the Lord, however, which ought to be our only rule in this
case, certainly prescribes greater moderation. For it teaches, that
the rigour of discipline ought not to be carried to such an extent, as
to overwhelm with sorrow the person whose benefit we are required
to regard as its principal object; as we have before shown more at
large.
 CHAPTER II.
THE TRUE AND FALSE CHURCH COMPARED.

We have already stated the importance which we ought to attach to

the ministry of the word and sacraments, and the extent to which
our reverence for it ought to be carried, so as to account it a
perpetual mark and characteristic of the Church. That is to say, that
wherever that exists entire and uncorrupted, no errors and
irregularities of conduct form a sufficient reason for refusing the
name of a Church. In the next place, that the ministry itself is not so
far vitiated by smaller errors, as to be considered on that account
less legitimate. It has further been shown, that the errors which are
entitled to this forgiveness are those by which the grand doctrine of
religion is not injured, which do not suppress the points in which all
believers ought to agree as articles of faith, and which, in regard to
the sacraments, neither abolish nor subvert the legitimate institution
of their Author. But as soon as falsehood has made a breach in the
fundamentals of religion, and the system of necessary doctrine is
subverted, and the use of the sacraments fails, the certain
consequence is the ruin of the Church, as there is an end of a man’s
life when his throat is cut, or his heart is mortally wounded. And this
is evident from the language of Paul, when he declares the Church
to be “built upon the foundation of the apostles and prophets, Jesus
Christ himself being the chief corner-stone.”[781] If the foundation of
the Church be the doctrine of the prophets and apostles, which
enjoins believers to place their salvation in Christ alone, how can the
edifice stand any longer, when that doctrine is taken away? The
Church, therefore, must of necessity fall, where that system of
religion is subverted which alone is able to sustain it. Besides, if the
true Church be “the pillar and ground of truth,”[782] that certainly can
be no Church where delusion and falsehood have usurped the
dominion.
II. As this is the state of things under the Papacy, it is easy to judge
how much of the Church remains there. Instead of the ministry of
the word, there reigns a corrupt government, composed of
falsehoods, by which the pure light is suppressed or extinguished.
An execrable sacrilege has been substituted for the supper of the
Lord. The worship of God is deformed by a multifarious and
intolerable mass of superstitions. The doctrine, without which
Christianity cannot exist, has been entirely forgotten or exploded.
The public assemblies have become schools of idolatry and impiety.
In withdrawing ourselves, therefore, from the pernicious
participation of so many enormities, there is no danger of separating
ourselves from the Church of Christ. The communion of the Church
was not instituted as a bond to confine us in idolatry, impiety,
ignorance of God, and other evils; but rather as a mean to preserve
us in the fear of God, and obedience of the truth. I know that the
Papists give us the most magnificent commendations of their
Church, to make us believe that there is no other in the world; and
then, as if they had gained their point, they conclude all who dare to
withdraw themselves from that Church which they describe, to be
schismatics, and pronounce all to be heretics who venture to open
their mouths in opposition to its doctrine. But by what reasons do
they prove theirs to be the true Church? They allege from ancient
records what formerly occurred in Italy, in France, in Spain; that they
are descended from those holy men, who by sound doctrine founded
and raised the Churches in these countries, and confirmed their
doctrine and the edification of the Church by their blood; and that
the Church, thus consecrated among them, both by spiritual gifts,
and by the blood of martyrs, has been preserved by a perpetual
succession of bishops, that it might never be lost. They allege the
importance attached to this succession by Irenæus, Tertullian,
Origen, Augustine, and others. To those who are willing to attend
me in a brief examination of these allegations, I will clearly show
that they are frivolous, and manifestly ridiculous. I would likewise
exhort those who advance them, to pay a serious attention to the
subject, if I thought my arguments could produce any effect upon
them; but as their sole object is to promote their own interest by
every method in their power, without any regard to truth, I shall
content myself with making a few observations, with which good
men, and inquirers after truth, may be able to answer their cavils. In
the first place, I ask them, why they allege nothing respecting Africa,
and Egypt, and all Asia. It is because, in all those countries, there
has been a failure of this sacred succession of bishops, by virtue of
which they boast that the Church has been preserved among them.
They come to this point, therefore, that they have the true Church,
because from its commencement it has never been destitute of
bishops, for that some have been succeeded by others in an
uninterrupted series. But what if I oppose them with the example of
Greece? I ask them again, therefore, why they assert that the
Church has been lost among the Greeks, among whom there has
never been any interruption of that succession of bishops, which
they consider as the sole guard and preservative of the Church?
They call the Greeks schismatics. For what reason? Because, it is
pretended, they have lost their privilege by revolting from the
Apostolical see. But do not they much more deserve to lose it, who
have revolted from Christ himself? It follows, therefore, that their
plea of uninterrupted succession is a vain pretence, unless the truth
of Christ, which was transmitted from the fathers, be permanently
retained pure and uncorrupted by their posterity.
III. The pretensions of the Romanists, therefore, in the present day,
are no other than those which appear to have been formerly set up
by the Jews, when they were reproved by the prophets of the Lord
for blindness, impiety, and idolatry. For as the Jews boasted of the
temple, the ceremonies, and the priesthood, in which things they
firmly believed the Church to consist; so, instead of the Church, the
Papists produce certain external forms, which are often at a great
distance from the Church, and are not at all necessary to its
existence. Wherefore we need no other argument to refute them,
than that which was urged by Jeremiah against that foolish
confidence of the Jews: “Trust ye not in lying words, saying, The
temple of the Lord, the temple of the Lord, the temple of the Lord,
are these.”[783] For the Lord acknowledges no place as his temple,
where his word is not heard and devoutly observed. So, though the
glory of God resided between the cherubim in the sanctuary, and he
had promised his people that he would make it his permanent seat,
yet when the priests had corrupted his worship by perverse
superstitions, he departed, and left the place without any sanctity. If
that temple which appeared to be consecrated to the perpetual
residence of God, could be forsaken and desecrated by him, there
can be no reason for their pretending that God is so attached to
persons or places, or confined to external observances, as to be
constrained to remain among those who have nothing but the name
and appearance of the Church. And this is the argument which is
maintained by Paul in the Epistle to the Romans, from the ninth
chapter to the twelfth. For it had violently disturbed weak
consciences, to observe that, while the Jews appeared to be the
people of God, they not only rejected, but also persecuted, the
doctrine of the gospel. Therefore, after having discussed that
doctrine, he removes this difficulty; and denies the claim of those
Jews, who were enemies of the truth, to be considered as the
Church, though in other respects they wanted nothing that could be
requisite to its external form. And the only reason for this denial
was, because they did not receive Christ. He speaks rather more
explicitly in the Epistle to the Galatians,[784] where, in a comparison
between Ishmael and Isaac, he represents many as occupying a
place in the Church, who have no right to the inheritance, because
they are not the children of a free mother. Hence he proceeds to a
contrast of the two Jerusalems, because as the law was given on
Mount Sinai, but the gospel came forth from Jerusalem, so many
who have been born and educated in bondage, confidently boast of
being the children of God and of the Church, and though they are
themselves a spurious offspring, look down with contempt on his
genuine and legitimate children. But as for us, on the contrary, who
have once heard it proclaimed from heaven, “Cast out the
bondwoman and her son,” let us confide in this inviolable decree,
and resolutely despise their ridiculous pretensions. For if they pride
themselves on an external profession, Ishmael also was circumcised.
If they depend on antiquity, he was the first born. Yet we see that
he was rejected. If the cause of this be inquired, Paul tells us that
none are accounted children but those who are born of the pure and
legitimate seed of the word.[785] According to this reason, the Lord
declares that he is not confined to impious priests, because he had
made a covenant with their father Levi to be his angel or messenger.
[786]
He even retorts on them their false boasting, with which they
were accustomed to oppose the prophets, that the dignity of the
priesthood ought to be held in peculiar estimation. This he readily
admits, and argues with them on this ground, because he was
prepared to observe the covenant, whereas they failed of
discharging the correspondent obligations, and therefore deserved to
be rejected. See, then, what such succession is worth, unless it be
connected with a continual imitation and conformity. Without this,
the descendants, who are convicted of a departure from their
predecessors, must immediately be deprived of all honour; unless,
indeed, because Caiaphas was the successor of many pious priests,
and there had been an uninterrupted series even from Aaron to him,
that execrable assembly be deemed worthy to be called the Church.
But it would not be tolerated even in earthly governments, that the
tyranny of Caligula, Nero, Heliogabalus, and others, should be called
the true state of the republic, because they succeeded the Bruti, the
Scipios, and the Camilli. But in regard to the government of the
Church, nothing can be more frivolous than to place the succession
in the persons, to the neglect of the doctrine. And nothing was
further from the intentions of the holy doctors, whose authority they
falsely obtrude upon us, than to prove that Churches existed by a
kind of hereditary right, wherever there has been a constant
succession of bishops. But as it was beyond all doubt that, from the
beginning even down to their times, no change had taken place in
the doctrine, they assumed, what would suffice for the confutation
of all new errors, that they were repugnant to the doctrine which
had been constantly and unanimously maintained even from the
days of the apostles. They will gain nothing, therefore, by persisting
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