Jee 2014 Booklet6 Hwt Organic Compounds

Vidyamandir Classes DATE :

TIME : 30 Minutes

MARKS : [ ___ /15]

TEST CODE : ORG CT [1]

START TIME :

END TIME :

TIME TAKEN:

PARENT’S 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

(B)

displacement of   electrons

delocalization of   electrons

(D)

displacement of   electrons

(C)

resonance effect

(D)

inductive effect

pp

(D)



II > I > IV > III

(D)

I > III > II > IV

(C) 3.

4.

5.

Electromeric effect is : (A) permanent effect

temporary effect

Hyperconjugation involves overlap of the following orbitals. p (A) (B) (C)  The correct stability order for the following species as :

(A) 6.

(B)

II > IV > I > III

(B)

I > II > III > IV

(C)

The electrophile, E  attacks the benzene ring to generate the intermediate   complex . Of the following, which   complex is of lowest energy?

(A)

(B)

(C)

(D)

7.

Orbital interaction between the   bonds of a substituent group and a neighbouring   orbital 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

9.

(C)

protons

(D)

None of these

C6H5OH

(D)

C6H5Cl

Which of the following species does not exert a resonance effect? 

(A) 10.

C6H5NH2

(B)

(C)

C6 H 5 N H 3

CH3CH2Cl undergoes homolytic fission, producing: 

(A)



CH3 C H 2 and Cl (B)

VMC/Organic Concepts







CH3 C H 2 and Cl (C)

1



CH3 C H 2 and Cl (D)





CH3 C H 2 and Cl

HWT-6/Chemistry

Vidyamandir Classes 11.

The rate of the reaction,

is influenced by the hyper conjugation effect of group R. If R sequentially is : CH3  CH 2 

III.

H3C  CH  | CH3

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

CH3 

I.

12.

II.

(B)

+I effect is shown by : (A) CH3 

14.

(D)

III, II, I, IV

Among the following the least stable resonance structure is : (A)

13.

IV.

CH3 | H3C  C  | CH3

(B)

(C)

Br

(C)

(D)

Cl

(D)

 NO 2

HBr

R 3 N  CH  CH 2   product . Predominant product is : 

(A) 15.

R 3 N  CH  CH3 (B) R 3 N  CH 2  CH 2  Br (C) | Br





CH 2  CH  N R 3 Br (D)

no reaction

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 CH3 in toluene. This is because : (A) of inductive effect due to CH3 in toluene (B) (C) (D)

of the presence of benzene ring in toluene of resonance among the structures of benzyl radical in toluene aromaticity of toluene

VMC/Organic Concepts

2

HWT-6/Chemistry

Vidyamandir Classes DATE :

TIME : 25 Minutes

MARKS : [ ___ /15]

TEST CODE : ORG CT [2]

START TIME :

END TIME :

TIME TAKEN:

PARENT’S 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 in kcal/mol) for CH4(A), C2H6 (B) and CH3Br (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 (A)

3.

(B)

C H 2  CH 2  C H  CH  O  CH 3

(D)

C H 2  CH  C H  C H  O  CH 3

(C)

CH3





C H 2  C H  CH  CH  O  CH3



Which of the following is the most stable cation? (A)

4.





C H 2  CH  CH  CH  O  CH3 

(C)

1-methoxy-1, 3-butadiene is least stable?





F3C  CH  2

 CH3 2 CH

(B)

(D)

CF3

II

(D)

all three N atoms

tetrahedral

(D)

linear

(C)

B>C>A

(D)

C>A>B

(C)

 C6H5 3 C

(D)

 CH3 3 C

Consider thiol anion (RS ) and alkoxy anion (RS ) . Which of the following statements is correct?

5.

(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

Which one of the nitrogen atoms in

O || is the most nucleophilic? H 2 N  NH  C  NH 2 I

(A)

III

(B)

II

I

(C)

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 sp3 hybridised

7.

Geometry of methyl free radical is (A) pyramidal (B)

8.

(C)

Relative stabilities of the following carbocations will be in the order 

(A) 9.

planar





C H3

CH3 C H 2

A

B

C>B>A

C H 2OCH3 C

(B)

Ca (B) b>a>c 5.

c>b>a

(D)

a>b>c

Which one of the following has the most nucleophilic nitrogen? (A)

6.

(C)

(B)

(C)

(D)

The correct sequence of steps involved in the mechanism of Cannizzaro’s 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 

VMC/Organic Concepts

5

HWT-6/Chemistry

Vidyamandir Classes 7.

8.

Iso-propyl chloride undergoes hydrolysis by: (A) SN1 mechanism (C) SN1 and SN2 mechanisms OH

the attack of : :OH  ion at the carboxyl group the abstraction of proton from the carboxylic group

(B)

13.

14.

15.

(C)

electrophilic substitution of I order nucleophilic substitution of I order

(D)

(B) (D)

electrophilic substitution of II order nucleophilic substitution of II order

Which of the following would react most readily with nucleophilies?

(A)

12.

transfer of hydride ion to the carbonyl group the deprotonation of PhCH2OH

C2H5Cl  aq.NaOH   C2H5OH  NaCl; This reaction is: (A) (C)

11.

(B) (D)

The least active electrophile is:

(A) 10.

SN2 mechanisms Neither SN1 nor SN2 mechanism

In cannizzaro reaction given: 2PhCHO  PhCH 2OH  PhCO 2 The slowest step is: (A) (C)

9.

(B) (D)

(B)

Dehydration of alcohol usually goes by (A) E1 mechanism (B) E2 mechanism

(C)

(D)

(C)

E1 cb mechanism (D)

SN2 mechanism

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 The electrophile involved in the sulphonation of benzene is : (A)

SO3

(I)

CH3CH 2 Br  C2 H 6 and

(II)

LAH  alkene , The reason for this is  CH3 3 CBr 

(A) (C)

(I) SN2, (II) E1 mechanism (I) SN1, (II) E1 mechanism

(B)

SO32 

(C)

H3O 

(D)

SO3

LAH

VMC/Organic Concepts

(B) (D)

6

(I) SN1, (II) E2 mechanism (I) SN2, (II) E2 mechanism

HWT-6/Chemistry

Vidyamandir Classes DATE :

TIME : 30 Minutes

MARKS : [ ___ /15]

TEST CODE : ORG CT [4]

START TIME :

END TIME :

TIME TAKEN:

PARENT’S 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.

2.

Protic solvent is : (A) diethyl ether

5.

(B)

In a compound

(C)

acetone

(D)

ethanol

(C)

(D)

electrophilic substitution has occurred. The substituent-E are: CH3, CH2Cl, …..; the increasing order

towards electrophilic substitution is as follows: (A) CH3   CH 2Cl   CHCl 2   CCl3

(B)

CH3   CHCl2   CH 2Cl   CCl3

CCl3   CH 2Cl   CHCl 2   CH 3

(D)

CCl3   CHCl2   CH 2Cl   CH 3

(C) 4.

n-hexane

Which of the following shows SN1 reaction most readily?

(A)

3.

(B)

Which one of the following compounds is most reactive towards nucleophilic addition? (A) CH3CHO (B) PhCOCH3 (C) PhCOPh (D)

CH3COCH3

Following reaction:

 CH3 3 CBr  H 2O   CH3 3 COH  HBr ; is an example of (A) solvolysis (C) nucleophilic substitution

(B) (D)

free radical substitution electrophilic substitution

6.

Which of the following is the correct order of decreasing SN2 reactivity? (X = a halogen) (A) RCH2X > R3CX > R2CHX (B) RCH2X > R2CHX > R3CX (C) R3CX > R2CHX > RCH2X (D) R2CHX > R3CX > R2CH2X

7.

The SN1 reactivity of the following halides will be in the order I. (CH3)3CBr II. (C6H5)2CHBr III. The correct choice is : (A) IV > I > II > III (B) (C) I > III > II > IV (D)

8.

The Kolbe’s electrolysis proceeds via (A) nucleophilic substitution mechanism (C) free radical mechansim

VMC/Organic Concepts

(B) (D)

7

(C6H5)2C(CH3)Br IV.

(CH3)2CHBr

II > I > III > IV III > II > I > IV

electrophilic addition mechanism electrophilic substitution reaction

HWT-6/Chemistry

Vidyamandir Classes

9. The electrophile is involved in the above reaction is : 

(A)

dichloromethyl cation (C HCl2 )

(B)

dichlorocarbene (: CCl2)

(C)

trichloromethyl anion (CCl3 )

(D)

formyl cation (C HO)



10.

Which of the following is arranged according to the nature indicated? 

(A)

Electrophile N O 2 , Br  , Nucleophile  CH3OH, N3

(B)

Electrophile N O 2 ,CH3OH, Nucleophile  Br  , N3

(C)

Electrophile CH3OH, N3 .Nucleophile  NO2 , Br 

(D)

Electrophile Br  , N3 , Nucleophile  CH3OH, N O 2





11.

12.

13.

14.

15.

Which of the following solvents are aprotic? (a) THF (b) SO2 The correct choice is : (A) A, B, C (B) A, C, D

(c)

CH3CN

(d)

CH3CO2H

(C)

B, C

(D)

A, C

(D)

ClCH 2  CH  CH 2

Which of the following is most reactive towards nuclephilic substitution reaction? (A) (B) C6H5Cl (C) C6H5CH2Cl CH 2  CH  Cl Vinyl chloride undergoes : (A) Only addition undergoes (C) Both (A) and (B)

(B) (D)

Only elimination reactions Substitution reactions

Which of the following is an electrophile? (A) H2O (B) SO3

(C)

NH3

(D)

ROR

Which of the following compounds will be most reactive towards nucleophilic addition reaction? (A) CH3COCH2CH2CH2CH3 (B) CH3CH2COCH2CH2CH3 (C)

CH3CH2CH2CH2CH2CHO

VMC/Organic Concepts

(D)

8

CH3  CH 2  CO  CH  CH3 | CH3

HWT-6/Chemistry