Vidyamandir Classes

VMC/Organic Concepts 1 HWT-6/Chemistry

DATE : TIME : 30 Minutes MARKS : [ ___ /15] TEST CODE : ORG CT [1]
START TIME : END TIME : TIME TAKEN: PARENTS SIGNATURE :
This test contains a total of 15 Objective Type Questions. Each question carries 1 mark. There is NO NEGATIVE marking.
Choose the correct alternative. Only one choice is correct.
1. The total number of contributing structures showing hyperconjugation
(involving C H bonds) for the following carbocation is :
(A) three
(B) five
(C) eight
(D) six
2. Inductive effect involves
(A) delocalization of electrons o (B) displacement of electrons o
(C) delocalization of electrons t (D) displacement of electrons t
3. Electromeric effect is :
(A) permanent effect (B) temporary effect (C) resonance effect (D) inductive effect
4. Hyperconjugation involves overlap of the following orbitals.
(A) o o (B) p o (C) p p (D) t t
5. The correct stability order for the following species as :
(A) II > IV > I > III (B) I > II > III > IV (C) II > I > IV > III (D) I > III > II > IV
6. The electrophile, E

attacks the benzene ring to generate the intermediate complex o . Of the following, which complex o is
of lowest energy?
(A) (B) (C) (D)
7. Orbital interaction between the bonds o of a substituent group and a neighbouring orbital t is known as :
(A) hyperconjugation (B) inductive effect (C) steric effect (D) electric qudrapole interactions
8. Mesomeric effect involves delocalisation of :
(A) pi-electrons (B) sigma electrons (C) protons (D) None of these
9. Which of the following species does not exert a resonance effect?
(A) C
6
H
5
NH
2
(B)
6 5 3
C H NH
+
(C) C
6
H
5
OH (D) C
6
H
5
Cl
10. CH
3
CH
2
Cl undergoes homolytic fission, producing:
(A)
3 2
CH CH and Cl
- -
(B)
3 2
CH CH and Cl

(C)
3 2
CH CH and Cl
-
(D)
3 2
CH CH and Cl
-
Vidyamandir Classes
VMC/Organic Concepts 2 HWT-6/Chemistry
11. The rate of the reaction,
is influenced by the hyper conjugation effect of group R. If R sequentially is :
I.
3
CH II.
3 2
CH CH III.
3
3
H C CH
|
CH

IV.
3
3
3
CH
|
H C C
|
CH

the increasing order of speed of the above reaction is :
(A) IV, III, II, I (B) I, II, III, IV (C) I, IV, III, I (D) III, II, I, IV
12. Among the following the least stable resonance structure is :
(A) (B) (C) (D)
13. +I effect is shown by :
(A)
3
CH (B) Br (C) Cl (D)
2
NO
14.
HBr
3 2
R N CH CH product

= . Predominant product is :
(A)
3 3
R N CH CH
|
Br

(B)
3 2 2
R N CH CH Br (C)
2 3
CH CH NR Br

=

(D) no reaction
15. C H bond energy is about 10 kcal/mol for methane, ethane and other alkanes but is only 77 kcal/mol for C H bond of CH
3
in
toluene. This is because :
(A) of inductive effect due to
3
CH in toluene
(B) of the presence of benzene ring in toluene
(C) of resonance among the structures of benzyl radical in toluene
(D) aromaticity of toluene
Vidyamandir Classes
VMC/Organic Concepts 3 HWT-6/Chemistry
DATE : TIME : 25 Minutes MARKS : [ ___ /15] TEST CODE : ORG CT [2]
START TIME : END TIME : TIME TAKEN: PARENTS SIGNATURE :
This test contains a total of 15 Objective Type Questions. Each question carries 1 mark. There is NO NEGATIVE marking.
Choose the correct alternative. Only one choice is correct.
1. The correct order of homolytic bond dissociation energies ( H A in kcal/mol) for CH
4
(A), C
2
H
6
(B) and CH
3
Br (C), under identical
experimental conditions is:
(A) C > B > A (B) B > C > A (C) C > A > B (D) A > B > C
2. Which of the following resonating structures of 1-methoxy-1, 3-butadiene is least stable?
(A)
2 3
CH CH CH CH O CH

= =

(B)
2 2 3
CH CH CH CH O CH

= =

(C)
2 3
CH CH CH CH O CH

(D)
2 3
CH CH CH CH O CH

3. Which of the following is the most stable cation?

(A)
3 2
F C CH

(B) , )
3
2
CH CH

(C)
3
CH

(D)
3
CF

4. Consider thiol anion (RS )

and alkoxy anion (RS )

.
Which of the following statements is correct?
(A) RS

is less basic and less nucleophilic than RO

(B) RS

is less basic but more nucleophilic than RO

(C) RS

is more basic but more uncleophilic than RO

(D) RS

is more basic but less nuclephilic than RO

5. Which one of the nitrogen atoms in

2 2
I II
O
||
H N NH C NH
is the most nucleophilic?
(A) III (B) I (C) II (D) all three N atoms
6. Which of the following is not true for carbanions?
(A) The carbon carrying the charge has eight valence electrons
(B) They are formed by heterolytic fission
(C) They are paramagnetic
(D) The carbon carrying the charge is sp
3
hybridised
7. Geometry of methyl free radical is
(A) pyramidal (B) planar (C) tetrahedral (D) linear
8. Relative stabilities of the following carbocations will be in the order
3 3 2 2 3
A B C
CH CH CH CH OCH

(A) C > B > A (B) C < B < A (C) B > C > A (D) C > A > B
9. Which one of the following carbanions is the least stable?
(A)
3 2
CH CH

(B) HC C

(C) , )
6 5
3
C H C

(D) , )
3
3
CH C

Vidyamandir Classes
VMC/Organic Concepts 4 HWT-6/Chemistry
10. The compound which gives the most stable carbocation on dehydration is :
(A) CH
3
CH(CH
3
)CH
2
OH (B) (CH
3
)
3
COH
(C)
2 2 2
cH CHCH CH OH = (D)
3 2 3
CH CHOHCH CH
11. With a change in hybridization of the carbon bearing the charge, the stability of a carbanion increase in the order
(A) sp < sp
2
< sp
3
(B) sp < sp
3
< sp
2
(C) sp
3
< sp
2
< sp (D) sp
2
< sp < sp
3
12. Which of the following intermediate have the complete octet around the carbon atom?
(A) Carbocations (B) Carbanion (C) Free radical (D) Carbene
13. Which one of the following is not true for the hydrolysis of t-butyl bromide with aqueous NaOH?
(A) Reaction occurs through the S
N
1 mechanism
(B) The intermediate formed is a carbocation
(C) Rate of the reaction doubles when the concentration of alkali is doubled
(D) Rage of the reaction doubles when the concentration of t-butyl bromide is doubled
14. t-butyl chloride preferably undergo hydrolysis by
(A) S
N
1 mechanism (B) S
N
2 mechanism (C) Any of (A) and (B) (D) None of the above
15. Which of the following statement regarding the S
N
1 reaction shown by alkyl halide is not correct?
(A) The added nucleophile plays no kinetic role in S
N
1 reaction.
(B) The S
N
1 reaction involves the inversion of configuration of the optically active substrate
(C) The S
N
1 reaction on the chiral starting material ends up with racemization of the product
(D) Polar protic solvent increases the rate of S
N
1 reaction.
Vidyamandir Classes
VMC/Organic Concepts 5 HWT-6/Chemistry
DATE : TIME : 25 Minutes MARKS : [ ___ /15] TEST CODE : ORG CT [3]
START TIME : END TIME : TIME TAKEN: PARENTS SIGNATURE :
This test contains a total of 15 Objective Type Questions. Each question carries 1 mark. There is NO NEGATIVE marking.
Choose the correct alternative. Only one choice is correct.
1.
3 3
CH Br OH CH OH Br

+ + reaction proceeds by S
N
2 mechanism. Its rate is dependent on the concentration of
(A)
3
CH Br, OH (B)
3
CH Br only (C) OH only (D)
3 3
CH Br, CH OH
2. The given compound : on hydrolysis inaqueous acetone will give :
[K]
[L]
[M]
(A) Mixture of (K) and (L) (B) Mixture of (K) and (M)
(C) Only (M) (D) Only (K)
3. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH is :
(A) 1 (B) 3 (C) 5 (D) 7
4. Consider the following bromides
(a) (b) (c)
The correct order is S
N
1 reactivity is :
(A) b > c > a (B) b > a > c (C) c > b > a (D) a > b > c
5. Which one of the following has the most nucleophilic nitrogen?
(A) (B) (C) (D)
6. The correct sequence of steps involved in the mechanism of Cannizzaros reaction is :
(A) nucleophilic attack, transfer of H

and transfer of H
+
(B) transfer of H

, transfer of H
+
and nucleophilic attack
(C) transfer of H
+
, nucleophilic attack and transfer of H

(D) electrophilic attack by OH

, transfer of H
+
and transfer of H

Vidyamandir Classes
VMC/Organic Concepts 6 HWT-6/Chemistry
7. Iso-propyl chloride undergoes hydrolysis by:
(A) S
N
1 mechanism (B) S
N
2 mechanisms
(C) S
N
1 and S
N
2 mechanisms (D) Neither S
N
1 nor S
N
2 mechanism
8. In cannizzaro reaction given:
OH
2 2
2PhCHO PhCH OH PhCO +

The slowest step is:

(A) the attack of : :OH ion

at the carboxyl group (B) transfer of hydride ion to the carbonyl group
(C) the abstraction of proton from the carboxylic group (D) the deprotonation of PhCH
2
OH
9. The least active electrophile is:
(A) (B) (C) (D)
10.
2 5 2 5
C H Cl aq. NaOH C H OH NaCl; + + This reaction is:
(A) electrophilic substitution of I order (B) electrophilic substitution of II order
(C) nucleophilic substitution of I order (D) nucleophilic substitution of II order
11. Which of the following would react most readily with nucleophilies?
(A) (B) (C) (D)
12. Dehydration of alcohol usually goes by
(A) E1 mechanism (B) E2 mechanism (C) E1 cb mechanism (D) S
N
2 mechanism
13. Arrange the following compounds in order of their decreasing reactivity with an electrophile, E

.
(a) Chlorobenzene (b) 2, 4-dinitrochlorobenzene (c) p-nitrochlorobenzene
The correct choice is :
(A) c > b > a (B) b > c > a (C) a > c > b (D) a > b > c
14. The electrophile involved in the sulphonation of benzene is :
(A)
3
SO
+
(B)
2
3
SO

(C)
3
H O
+
(D) SO
3
15. (I)
LAH
3 2 2 6
CH CH Br C H and
(II) , )
LAH
3
3
CH CBr alkene , The reason for this is
(A) (I) S
N
2, (II) E1 mechanism (B) (I) S
N
1, (II) E2 mechanism
(C) (I) S
N
1, (II) E1 mechanism (D) (I) S
N
2, (II) E2 mechanism
Vidyamandir Classes
VMC/Organic Concepts 7 HWT-6/Chemistry
DATE : TIME : 30 Minutes MARKS : [ ___ /15] TEST CODE : ORG CT [4]
START TIME : END TIME : TIME TAKEN: PARENTS SIGNATURE :
This test contains a total of 15 Objective Type Questions. Each question carries 1 mark. There is NO NEGATIVE marking.
Choose the correct alternative. Only one choice is correct.
1. Protic solvent is :
(A) diethyl ether (B) n-hexane (C) acetone (D) ethanol
2. Which of the following shows S
N
1 reaction most readily?
(A) (B) (C) (D)
3. In a compound electrophilic substitution has occurred. The substituent-E are: CH
3
, CH
2
Cl, ..; the increasing order
towards electrophilic substitution is as follows:
(A)
3 2 2 3
CH CH Cl CHCl CCl < < < (B)
3 2 2 3
CH CHCl CH Cl CCl < < <
(C)
3 2 2 3
CCl CH Cl CHCl CH < < < (D)
3 2 2 3
CCl CHCl CH Cl CH < < <
4. Which one of the following compounds is most reactive towards nucleophilic addition?
(A) CH
3
CHO (B) PhCOCH
3
(C) PhCOPh (D) CH
3
COCH
3
5. Following reaction:
, ) , )
3 2 3
3 3
CH CBr H O CH COH HBr + + ;
is an example of
(A) solvolysis (B) free radical substitution
(C) nucleophilic substitution (D) electrophilic substitution
6. Which of the following is the correct order of decreasing S
N
2 reactivity? (X = a halogen)
(A) RCH
2
X > R
3
CX > R
2
CHX (B) RCH
2
X > R
2
CHX > R
3
CX
(C) R
3
CX > R
2
CHX > RCH
2
X (D) R
2
CHX > R
3
CX > R
2
CH
2
X
7. The S
N
1 reactivity of the following halides will be in the order
I. (CH
3
)
3
CBr II. (C
6
H
5
)
2
CHBr III. (C
6
H
5
)
2
C(CH
3
)Br IV. (CH
3
)
2
CHBr
The correct choice is :
(A) IV > I > II > III (B) II > I > III > IV
(C) I > III > II > IV (D) III > II > I > IV
8. The Kolbes electrolysis proceeds via
(A) nucleophilic substitution mechanism (B) electrophilic addition mechanism
(C) free radical mechansim (D) electrophilic substitution reaction
Vidyamandir Classes
VMC/Organic Concepts 8 HWT-6/Chemistry
9.
The electrophile is involved in the above reaction is :
(A) dichloromethyl cation
2
(CHCl )

(B) dichlorocarbene (: CCl

2
)
(C) trichloromethyl anion
3
(CCl ) (D) formyl cation (CHO)

10. Which of the following is arranged according to the nature indicated?

(A) Electrophile
2 3 3
NO , Br , Nucleophile CH OH, N
+
+

(B) Electrophile
2 3 3
NO , CH OH, Nucleophile Br , N
+
+

(C) Electrophile
3 3 2
CH OH, N . Nucleophile NO , Br
+ +

(D) Electrophile
3 3 2
Br , N , Nucleophile CH OH, NO
+
+

11. Which of the following solvents are aprotic?
(a) THF (b) SO
2
(c) CH
3
CN (d) CH
3
CO
2
H
The correct choice is :
(A) A, B, C (B) A, C, D (C) B, C (D) A, C
12. Which of the following is most reactive towards nuclephilic substitution reaction?
(A)
2
CH CH Cl = (B) C
6
H
5
Cl (C) C
6
H
5
CH
2
Cl (D)
2 2
ClCH CH CH =
13. Vinyl chloride undergoes :
(A) Only addition undergoes (B) Only elimination reactions
(C) Both (A) and (B) (D) Substitution reactions
14. Which of the following is an electrophile?
(A) H
2
O (B) SO
3
(C) NH
3
(D) ROR
15. Which of the following compounds will be most reactive towards nucleophilic addition reaction?
(A) CH
3
COCH
2
CH
2
CH
2
CH
3
(B) CH
3
CH
2
COCH
2
CH
2
CH
3
(C) CH
3
CH
2
CH
2
CH
2
CH
2
CHO (D)
3 2 3
3
CH CH CO CH CH
|
CH