Organic Chemistry Reaction Mechanisms Quiz
Organic Chemistry Reaction Mechanisms Quiz
Level-1
SECTION - A
3. C = CH2 HCl The major product of the
Straight Objective Type |
CH3
This section contains multiple choice questions. Each reaction is :
question has 4 choices (A), (B), (C) and (D) for its
answer, out of which ONLY ONE is correct.
(A) (B)
1. Which one of the following compounds undergoes Cl Cl
bromination of its aromatic ring at the fastest rate?
(C) (D)
(A) (B)
NH Cl Cl
(C) (D) F F F F F
NH NH
4.
O HC
3
O2N O ON
2 NO2
NO2
2. Identify the set of reagents/reaction-conditions ‘X’ I II III IV V
and ‘Y’ in the following set of transformation
Br Ease of nucleopilic substitution among these
|
X Y
: CH3 CH2 CH2Br Pr oduct CH3 CH CH3 compounds will be in the order.
(A) X = dilute aqueous NaOH, 20°C; Y = HBr/ (A) II > III > IV > I (B) I > II > III > IV > V
CH3COOH. 20°C
(C) V > II > III > I > IV (D) IV > III > II > I > V
(B) X = conc. alcoholic NaOH, 80°C; Y = HBr/
CH3COOH 5. Which of the following compounds has a C–H
bond with the lowest bond dissociation energy ?
(C) X = dilute aqueous NaOH, 20°C; Y =
BrCHCl3, 20°C (A) C2H6 (B) C6H6
(1)
11. 2- Methylpent - 2, 3-diene is achiral because it
C CH
has
+
Hg+2/H (i) NaOH + I2
6. A + B . Then B (A) a centre of symmetry
H2O (ii) H3O
is
(B) a plane of symmetry
O CH 2 COOH
(C) a C2 axis of symmetry
(A) C CH3 (B)
(D) both centre and a plane of symmetry
O O 1. B2D6
12. CH3–CH=CH 2
C COOH C OH 2. H2O 2/OH –
(C) (D)
X is :
7. Which of the following alcohols is dehydrated
most readily with conc. H2SO4? (A) H3C—CH—CH2D (B) H 3C—CH—CH 2OH
OH D
(A) p–NO2C6H4 CH(OH)CH3
(C) H 3C—CH—CH 3 (D) None of the above.
(B) p–CH3OC6H4CH(OH)CH3
OD
(C) p–Cl C6H4 CH(OH) CH3 NH4Cl
product
13. CH CH Cu2Cl2
I II III IV V CH
C
(A) IV > V > II > III > I (B) I > II > III > V > IV HOBr (excess)
14.
(C) III > I > III > V > IV (D) V > IV > II > III > I
(A) I < IV < II < III (B) IV < I < II < III
(C) IV < I < III < II (D) IV < II < I < III.
(A) CH3CCH3,(CH3)3CHO D
O
CH3
dil H2SO4
P2
(B) CH 3CCH 3,(CH 3)3C – COOH
D
O
OH H
(C) CH3COH,(CH)3CCOOH
CH3 CH3
(D) None is correct
(A) and
D D
16. Compound ‘A’ (C16H16) on ozonolysis gives only
H OH
one product ‘B’, (C 8H 8O). ‘B’ gives positive
lodoform test and forms sodium benzoate as one
of the product. Identify the structure of ‘A’. H OH
CH3 CH3
(A) Ph–CH2–CH = CH–CH2–Ph
(B) and
CH3 Ph D D
(B) CH3–C = C – Ph OH H
OH OH
(C) Ph – C = C – Ph
CH3 CH3
CH3 CH3
(C)
CH3 and
D H
(D) Ph – CH = C – CH 2 – Ph H D
CH3 C NH 2
||
H H
17. Br
Mg / dry ether
(X)
O
(Y ) H D
(D)
and
The structures of (X) and (Y) respectively are H OH
CH3 H
(A) X = MgBr ; Y= OH
CH3 H 18
(i) CH3COOOH
19. X
(ii) H3 O
(B) X= Br ; Y= OH
H CH3
Mg OH
(C) X = MgBr ; Y=
CH3 CH3
18 18
H OH H OH
(D) X = BrMg MgBr ; Y = HO OH (A) (B) HO H
H OH
CH3 CH3
(3)
CH3 CH3 25. The correct order of stabi lity of f ollowing
18 carbocation is :
H OH H OH
(C) H (D) H 18
OH OH
CH3 CH3 (I) (II)
OH OH (III) (IV)
(A) (B)
OH OH
(A) (III) > (II) > (I) > (IV)
O (B) (II) > (III) > (I) > (IV)
(C) (D)
(C) (I) > (III) > (IV) > (II)
22. W hi ch of the f ollowing set of groups are (A) I and IV (B) I and II
deactivating but ortho-para directing?
(C) II and III (D) III and II
(A) –CHCl2, –CH2Cl (B) –CCl3, –NO2
27. A hydrocarbon (C 6H 8) absorbs two moles of
(C) –Cl (D) –NH2, –OCH3 hydrogen in the presence of a platinum catalyst.
The reduction product is inert to bromine and
KMnO4 solution. The hydrocarbon on ozonolysis
23. produces malonic acid only. The structure of
hydrocarbon is
(A) (A) CH2 = CH – CH = CH – CH = CH2
H3C
(B)
(B)
(C)
(C)
(D)
(A) C6H6 (B) C6D6 34. An alkyl halide (X) having molecular formula
••
C6H13Cl reacts with (CH3)3 COK+ to form two
(C) C6T6 (D) Same in all
isomeric alkenes (Y) and (Z) of molecular formula
C6H12. Both alkenes gives 2, 3-dimethyl butane on
CH3
1) Hg(OAc)2/H2 O hydrogenation. The halide (X) is ?
30. CH3–CH–CH=CH2 Major product is?
2) NaBH4
CH3
CH3 CH3 (A) CH3 – CH – CH – CH2 – Cl
CH3
(A) CH3–C–CH–CH2 (B) CH3–C–CH–CH3
H H OH H OH (B) CH3 – CH2 – CH2 – CH – CH2 – CH3
Cl
CH3 CH3
(C) CH3 –C – CH2 – CH3 (D) CH2 –C – CH2 – CH3 CH3 CH3
OH OH H (C) CH3 – C – CH – CH3
31. On monochlorination of Methylcyclohexane, the Cl
total number of structural isomers produced is
CH3
(A) 2 (B) 5 (D) CH3 – C – CH2 – CH2 – CH3
(C) 6 (D) 8 Cl
(5)
36. Which of the following majorly formed during this CH 3
reaction? H OH
(C) (r) Optically active
H OH
CH3
H3O
OH H H
(D) C C C C (s) Optically inactive
OH Cl
Cl
C CH 3
to internal (A) CH 2 .C H 3
(p) Birch
CI HO
compensation reduction
O
compensation intermediate
D2
(C) Me–C C– Me (r) W olf -Kishner
(C) (r) Product has two
Ni reduction
chiral centre O
Br2
(D) (s) Clemmensen
(D) H2O
(s) Diastereomers will be
reduction
formed
X Y Z (vi) and
0 0 0
1 1 1
H
2 2 2
(vii) H and H
3 3 3
H
4 4 4 H H
H
5 5 5 (viii)
and
6 6 6
7 7 7
8 8 8 OH OH
9 9 9
and
(ix)
Cl F
41. Among the various acid pairs, in how many pairs
former acid is having more stable conjugate base
than later one? COOH
COOH
and
OH (x)
COOH
(ii) CF3COOH and CH3COOH 42. The total number of products (excluding
stereoisomers) possible by monohalogenation of
isopentane are ______.
(iii) CH2 = CH–COOH and CH C – COOH 43. Hydration using H3O+ introduces OH at carbon
OH OH ..................... in the following :
NO2
(iv) 6
and
7 5
2
NO2 8 4 3 1
9
COOH COOH
44. The addition of bromine to 3-Methyl Cyclohexene
CH3 produces ____ dibromo derivatives:
(v) and
CH3
(7)
45. How many 1, 2-Shifts are involved during the 46. A compound of carbon, Hydrogen and nitrogen
course of following reaction : contains the element in the ratio of 18 : 2 : 7 (by
mass). Find the ratio between molecular mass and
+ empirical mass (molecular mass = 108).
+ 47. Number of monochlorinated product obtained by
monochlorination of 2, 2, 3, 3 - tetramethyl butane
is
H
SECTION - A Et Me
Me Et
Straight Objective Type (A) (B)
This section contains multiple choice questions. Each
question has 4 choices (A), (B), (C) and (D) for its
answer, out of which ONLY ONE is correct.
(C) C2H4 (D)
1. Consider the following reaction :
H3PO4
+ 4. Which of the following compounds is formed in a
OH Heat major quantity when reacted with H+ ion ?
Which response contains all the correct statement
HC—CH—CH—CH CH2
about this process? 2 2
1. Dehydration CH3
H+ major product
2. E2 mechanism
3. Carbon skeleton migration
4. Zaitsev elimination as major product
H2C
5. Primary Kinetic Isotope Effect CH2
(A) 1, 3 (B) 1, 2, 3 (A)
CH–CH3
(C) 1, 2, 5 (D) 1, 3, 4
2. Identify correct order of reactions in following H2C–CH3
sequence of organic synthesis.
OM e O
(B)
1. AICI3 Zn(Hg)
+ O [A] HCl [B]
2. H3O+
O O Me Et
MeO H3 PO4 (C) Both (A) and (B)
COOH
(B)
, Friedel-Crafts (C) (D)
COOH
COOH
O3, Zn / HO
2
(C) 3-Oxobutanal only
, Diels Alder 10. [X]
COOH
H2/ Ni Cl2 /hv
Y
COOH
Four monochloro
(D) structural
, Friedel-Crafts
COOH isomeric products
Compound ‘X’ is :
7. Find the incorrect observation :
(A) 1-Methylcyclopropene
(A) 1, 1 - or 2, 3 - or 1, 2 or 2, 2 - dibromo
(B) 1, 4-Dimethylcyclohexa-1, 4-diene
pentane on heating with KOH give pent-2-yne
(C) 1, 4-Dimethylcyclohexa-1, 3-diene
(B) CH2 = C(CH3) – CH = CH2 reacts with HCl
only through a 3° - allylic carbocation (D) 1, 2-Dimethylcyclohexa-1, 4-diene.
1. CF3COOH
(II) CH3
(Catalytic amount)
(C) OH 2. B H /THF
2 6
–
3. H2O2/OH
(III)
Br
(A) I, III (B) II, III
(D) OCH3
(C) I only (D) III only HBr/CH3OH
13. W hich of the following can be used for the
nitration of Benzene 16. The following compound generally gives anti-
addition of Br2. But, on increasing the polarity of the
(A) NO2 CIO4 (B) N2O5 solvent the extent of anti-addition decreases. What
might be the possible reason?
(C) (1) and (2) both (D) N2H4
[Link] Cl2 1 eq [Link] (B) Highly polar solvent prevents the nucleophile to
(B) *CH3I [Link]
3.*CH3I
h [Link]
3.*CH3I attack from the back
Na Cl2 Na
(C) Highly polar solvent destabilises the benzyl
(C) *CH3I ether h ether carbocation to be formed
Cl2
* *
CH3 –CH2 – I (D) Steric crowding of the substrate alters the
(D) *CH I Na
3 ether h Na/ether reaction mechanism
17. Following are some reactions related to reactions
15. Your job is to synthesis few compounds starting
of alkadiene and alkyne. Find which is incorrectly
from methylenecyclopentane
(reaction/comment) shown?
CH2 CH3
CH2
HBr
(1 equivalent)
(A) (PhCO)2O 2 h Br
Thermodynamic
The targets and the required regents are given. product
Find the wrong match.
O COOH
CH3
(A)
1. Catalytic amount of CF3COOH
2. Hot alkaline KMnO4
+
3. H
(11)
CH2Br
(A)
(B) CH2 = CH – C = CH2 CH 3
HCl
(1 equivalent) Br
CH3
(B) CH2
Cl
CH 3
CH2 = CH – C – CH3
(C) CH2
CH3
CH 3 Br
(Kinetic product)
19. Which of the following product(s) is (are) formed in (D) P1 can also be obtained by ozonolysis of 2, 3-
the given reaction? dimethylbut-2-ene.
CH3 CH3
(C) : 1, 4-addition
(C) CH3–CH (D) CH3–CH
| |
CH3 CH3
(D) : 1, 4-addition
Cl Paragraph for Question Nos. 25 and 26
Compounds A and B are one pair of ring-chain isomers
SECTION - C
of hydrocarbon. Similarly, C and D form another pair. A
is quite stable to oxidation in presence of alkaline
Linked Comprehension Type
KMnO4 while ‘C’ undergoes oxidation without any loss
of carbon atoms. Compounds B and D on ozonolysis
This section contains paragraphs. Based upon this consume 1 mole of O3 each. ‘D’ gives two moles of
paragraph, some multiple choice questions have to be acetaldehyde on ozonolysis while ‘B’ gives only one
answered. Each question has 4 choices (A), (B), (C) and mole. Note that ‘D’ is just one carbon higher homologue
(D) for its answer, out of which ONE/MORE is/are correct. of ‘B’
25. Addition of HCl follows Markovnikov’s rule in
Paragraph for Question Nos. 23 and 24 compound
(A) Only B (B) Only C
(C) Both ‘B’ and ‘C’ (D) Both ‘A’ and ‘B’
CH3 H 1. M g/ether
PCC 26. Which of the followig reagents give identical products
C=C A
O CH 2Cl2
CH 3 CH 2 – Br 2. when react with ‘C’ and ‘D’ separately?
3. H3 O
+ CH3 (A) H2/Ni (B) Cl2/CCl4
(C) DCl (D) None of these
SECTION-D
[Link] 3/THF
B C
2.H2 O2 /NaOH Matrix-Match Type
3. PCC/CH2 Cl2
This Section D have “match the following” type question.
Question contains two columns, Col-I and Col-II. Match
23. Product ‘A’ contains the entries in Col-I with the entries in Col-II. One or more
entries in Col-I may match with one or more entries in
(A) One double bond and one –OH group Col-II.
(B) Only one double bond 27. Match the following question Column–I with
Column–II :
(C) Only one –OH group
Column-I Column-II
(D) One double bond and one –CHO group
Br
HCOOH
24. Product ‘C’ can also be obtained (along with some (A) H 25°C (p) Ei
other byproduct) from ozolysis of which of the CH 3
following alkene
–
(B) CHBr/OH
3 (q) Substitution
(13)
28. How many of the following are more stabilized in
their Gauche conformation instead of their Anti–
(C) (r) Cyclopropane ring condormation.
+
formation
N OH – ClCH2CH2Cl; CH3CH2CH2CH3 ; FCH2CH2F
H 3C CH3
H H H2NCH2CH2OH; NH2CH2–CH2–COOH;
(D) H 3C Ph (s) SN1
+
HOOCCH2CH2COOH (at low pH)
N (CH3) 2
Ph
O
–
29. How many products will be formed excluding
stereo when cis-1, 3, 5-trimethyl cyclohexene
(t) E2 reacts with NBS?
4) Acetic acid
X Y Z
5) Phenol
0 0 0
1 1 1 6) Acetylene
2 2 2
3 3 3 O
4 4 4 7) Cl3 S OH
5 5 5 O
6 6 6
7 7 7 8) CF3COOH
8 8 8
9 9 9
9)
LEVEL-1
13. (B) 14. (A) 15. (B) 16. (C) 17. (C) 18. (B)
19. (A) 20. (D) 21. (A) 22. (C) 23. (A) 24. (B)
25. (D) 26. (C) 27. (C) 28. (B) 29. (D) 30. (B)
31. (B) 32. (A) 33. (B,C) 34. (C) 35. (A,C,D) 36. (D)
40. (A-r,B-r,C-p,q,D-r,s) 41. (3) 42. (4) 43. (3) 44. (4)
LEVEL-2
13. (C) 14. (B) 15. (D) 16. (A) 17. (D) 18. (B,D)
19. (A,B,C,D) 20. (A,C,D) 21. (A,B,D) 22. (B,D) 23. (A) 24. (B)
25. (C) 26. (A) 27. (A-q,s,B-r,C-t,D-p) 28. (3) 29. (3)
30. (9)
(15)