DATE.

NO,
problem 1-I
a. O H- H .I F 5t .C
CỘH-N
H
e 0. H3C- CI
C. - +
n. H,N - OH

Problem 1-16.
Give each aton hte appropriate formal charge.

a.r CH3-Q-CH3 -6 3-2=1 b. M - C H- 4 - 3 - 2 ==1

CH3
.C CH3 - N - CH3 5-4=1 ? H- N- B-H =N 5 - 4 =
CH3
+ H H. =B 3-4= =1

Problem 1-17.
Praw the Lewis structure for each of the folowing
a. Nº3° b. NO2* .C CH5 +d c ,
-0-N-0 O=N=0 H- C - C : - C*
H

.C H
C NH, f. NaOH 9. HCO5 .h HCO2
+

H- C - N - H
H

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DATE.

Problem 1-22.
Change the folowina condensed structues ot kekulé structures.
a.CH3 NHCCH); CH3. .b (CH3)2 CHC).
H

CH3 M
'
{
CH3
1 - C- N- C - C - M 043- C- Cl
HH

.C (CH.)3 CBr. d . (CH,), C(CH); C

CH3 C- = Br. CH3 - C - C- C - C -

Problem 1-27
What orbitals are used to form the ol sgima bonds ni propane?
H H M 10 S P,
H- C- C- C- 1 . [5P3)
п н н

Prodem 1-32.
.4 42C0г. 2. HCN• 3. CCl 4. C03.

CI
0 1

H- C-OH H- C E N O-C-
SP
di
SP2.
SP3 SP2
 DATE NO

Problem 1-33
Predict the approximate bond angles in
a methyl cation b". methyl radical. C.' methyl anion.

H- C-H. H- C - N

8=120° Đ22/0°, 0<120° 0 ~ 101.3°

Problem 1-39.
lfi nig compen.
Descrbie het orbitals used ni bondnig and hte band anglesni het m
. 30. - b . СОг. C. EH C
O
SP3, O~ 109.5° 0=(=0 SP, 0=180° SP2, 02120°
1 - CoM
H
=0 GH

d. Nz e . BF
NEN SP, 9=180° SP2, 0=120°

Problem 1-45
Predict hte approximate band andles To.r
0~ 109. 5°
CH - N-H. 0 ~ 107. 3°
6i
-j

013
02 /07- 3° d. 8~104.5°
4- C - C - N :
H

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Probem 1-46
Whchi of het folbring mecules woudl you expect ot have a dpioel of ser?
l Sonilg Strategy.
oT anower parts of and h, you may ned reveiw hte Porbem
a. CHC
, Hs. .b H2C=0 C
. CH2C/2. .d NHs/

c. H2C=CH2 A HC
, =CHBr. 2. Bela h. BF 3

Problem 1-170
Indicate het formal charge no each carbon htat has one. lAenle pasi ear nhsi
4- 3-2
- C
H 4-3 14- C • 4 - 3 - 1 1-C-h 422
H 4 [0)

=, = =,
10
 DATE. NO

Problem 2-3.
Draw the products of the acid - base reaction when.
a. acid-HCl, Base- NH .s b. acid - 12o, base - NHa.
C +NH, >= NHÀ +CI
H H20 + NHE =>. WH3 +H
O

Problem 2-7.
Butric a c i d, hte compound responsible for hte unpleasant odor and taste of
sour milk, has a pla value of 4.82. What si its ta valve? Is ita
stranger acid or weaker acid htan vitamin C ?

a 104:82 ,
K C ka= 10:4/m
Pka .

Problem 2-10
Draw the convaate act of each of the folving.
a. CH3CH20H: b. CH3 CH20 C . 0

*, CH3c20
CHs

:d 3 NHz e. 0
.
t0 - н
TI
2 NH3
CH, C
H /
→ C
CH3CHг ОН. L
H
CH,C
H

Problem. 2-13
Whcih is a stranger base: CHa C
OU ar HCOO? CH3 C00
1 / 1, “ (/ 1 : 10. or NH2? -N
H 2.
1 " - H20 3 ? H20

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Problem 2-17
Darw hte caratin, showne equilibion arrows that incicate whehter
reactants at products are favored, for the acid-base reaction of ehtnewhti
а НО- b.
M =C
2/ +Ò
C2H o
H +M

C, 10 MH .

Problem 2-23.
c.i Draw the prodcts of the folowing readions
A HC= + , , 5 T CaH +CH3CH3
В Н
Е
С =СН НСЕС → ПС=СН + НСЕСН
C Os 3+ HC 2 OiCe+ HC
b. Whcih of hte reactims favor famation of hte produets?
CH1-C
, 1, . A

Pablem 2-27.
Whcih si a stranger acid?
a . HC o r HBr .6 Ch, , , Ch ,Cn.
, , ,o 2
4414
H-c-C-c- 0-1

d. C 3 2 CHaCH2OHSH
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Problem 2 - 3 2
Whcih is a stranger borse?
:b
CH3 CHCO 0 0304t0
CL

BrCH,CH,CO- CH3CH, O
C c ha te,o-
Problem 2-34.
For each of the falwing compands, indicate hte atom that is protonated
when an acid si outed to a solution of t h e compound
a.
N, 0.
١
CH|3 003 CHl3 NH2.
0-
N, 0.
N
CH
S
Problem 2-49.
. N .
C.

CH, 04
C o
CHICH
TNH3
NH2.
e. .
f, C
.

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O

Problem 2-48
P woudl you make hte water layer ot cause hte cabroxy cil
a. What H
acid ot dissolve ni hte water layer and hte amine ot dissolve
ni hte ether lover?
ph 68. .

.b P 87 .

Problem 2-51
Darw hte products of hte folwng reactions. U
es curved arows ot show
Where the pair ofelectrons starts and where it ends up.
17 -

6. Febra + B
L
: ← Fe - B
Br

Problem 2-54.
Praw caned arrows ot show where the electrons and whore they end ni hte
followiz reactions.

a. NHs +H-CI:
b. H20:+ FeBr H2O- Febr3
+0
(. + H- C1 +: c/