Corrected

Alkyl and Aryl Halides

Level 1

Test
Friday 29th April, 2016
Name:
Roll Number:

The hybridization of carbon attached to the halogen in alkyl halide and aryl halide respectively is
A

sp3 , sp2

A
4

sp2 , sp3

chloramphenical

sp3 , sp3

sp2 , sp2

aspirin

thyroxine

teflon

1chloropropene

chloroethene

Which of these is allylic halide?

B

4chlorocyclohexene

3chloropropene

The order of dipole moment amongst methyl halides is

A
B
C
D

Which of these compounds does not contain halogen?

A

CH3 F > CH3 Cl > CH3 Br > CH3 I

CH3 F > CH3 Br > CH3 I > CH3 Cl
CH3 Cl > CH3 F > CH3 Br > CH3 I
CH3 I > CH3 Br > CH3 Cl > CH3 F

The best method amongst these to prepare alkyl iodide from alcohol will be
B

A Heating with sodium or potassium iodide in 95% phosphoric acid

C heating with SO2 + I2
Constant boiling with concentrated HI and Red Phosphorus
D Heating with sodium or potassium iodide in 98% sulphuric acid

6
How many compounds are possible (including stereoisomers) on mono chlorination of isopentane?
0 1 2 3 4 5 6 7 8 9
7

The product of the following reaction

CH3
F e,dark

+ Br2
A

B benzyl bromide
mixture of o, m and p-bromotoluene
D mixture of o and p-bromotoluene

m-bromotoluene

Corrected
8

Which of these reaction will not produce a haloarene?

+
N2 X
KI

+
N2 X

Cu Br

Cu Cl

2
2

B
9

+
N2 X

+
N2 X

2
2

Cu F

2
2

Which of these reactions gives alkyl iodide as the organic product?

A
B

Sandmeyers reaction
Finkelstein Reaction

Gatermann Reaction

Swarts Reaction

10
An alkane of molecular formula C5 H12 , on photochemical mono chlorination gives a single product. The
alkane is
A
11

cyclopentane

neopentane

isopentane

npentane

Gem dibromide is
A

12

B CH2 BrCH2 Br
CH2 (Br)CH2 CH2

CH3 CH(Br)OH(Br)CH3
D

CH3 CBr2 CH3

Benzylidene chloride is
A

C6 H5 CCl3

C6 H5 CH2 Cl

C6 H5 CHCl2

C6 H4 ClCH2 Cl

13
Number of bonds present in B.H.C. (Benzene hexachloride) are
0 1 2 3 4 5 6 7 8 9
14

Preparation of alkyl halides in laboratory is least preferred by

A

B Treatment of alcohols
C Direct halogenation of alkanes
D Addition of hydrogen halides to alkenes

Halide exchange

15
The product of the following reaction :
CH2 = CH CCl3 + HBr
A

BrCH2 CHCl CHCl2

D

16

CH3 CH2 CCl3

Which of the following would be produced when acetylene reacts with HCl
A

17

B CH3 CH(Br) CCl3

CH2 (Br) CH2 CCl3

CH2 = CHCl

CHCl = CHCl

CH3 CH2 Cl

Which of the following does not decolourise bromine solution in carbon disulphide
Propyne

Propene

Ethane

Acetylene

CH3 CHCl2

Corrected
18
What is the chief product obtained when nbutane is treated with bromine in the presence of light at
130o C
CH3
A

CH3

CH2

CH

Br

CH3

CH3
D
19
A

20

A
23

CH3

CH3
CH2 CH2 Br

B 2bromo2methylbutane
D 1bromo2methylbutane

2bromo3methylbutane

Br

CH3

1bromo3methylbutane

Addition of bromine to 1, 3butadiene gives

1, 2 addition at low temperature and 1, 4 addition product at high temperature
1, 2 addition at high temperature and 1, 4 addition product at low temperature
C 1, 4 addition product only
D 1, 2 addition product only

The intermediate during the addition of HCl to propene in the presence of peroxide is

A
22

CH2

CH2 Br

2Methylbutane on reacting with bromine in the presence of sunlight gives mainly

A
B

21

CH3

CH

CH3 CH2 CH2

CH3 CHCH3

CH3 CHCH2 Cl

CH3 CH2 CH2

How many gm of bromine will react with 21 gm C3 H6

160

80

320

240
Pyridine

The following reaction is known as C2 H5 OH + SOCl2 C2 H5 Cl + SO2 + HCl

A

Kharasch eect

Hunsdiecker synthesis reaction

D Darzens procedure

Williamsons synthesis

+
N2 BF4

24

In the above process product A is

A
25

1, 3difluorobenzene

Fluorobenzene

1, 4difluorobenzene

Benzene

CS

2
Silver acetate+ Br2 .
The main product of this reaction is

CH3 COI

None of these

CH3 COOH

CH3 Br

Corrected
26
In methyl alcohol solution, bromine reacts with ethylene to yield BrCH2 CH2 OCH3 in addition to 1,
2dibromoethane because
A

27

B The reaction follows Markownikos rule

This is a freeradical mechanism
C The methyl alcohol solvates the bromine
D The ion formed initially may react with Br or CH3 OH

The final product obtained by distilling ethyl alcohol with the excess of chlorine and Ca(OH)2 is
A

CHCl3

CCl3 CHO

CH3 CHO

(CH3 )2 O

28
Which one of the following processes does not occur during formation of CHCl3 from C2 H5 OH and
bleaching powder
A
29

Oxidation

Chlorination

Reduction

Hydrolysis

Which compound does not form iodoform with alkali and iodine
A

Isopropyl alcohol

Acetone

Diethyl ketone

Ethanol

30 How many total products are formed (including stereo isomers) when a mixture of cis and trans pent2ene
is treated with bromine in carbontetrachloride?
0 1 2 3 4 5 6 7 8 9
31

Find the major product in the following reaction

CH3
CH3

CH

ZnCl2

CH3 + HCl

CH3 OH
CH3
A

CH3

CH3Cl
CH

CH3

CH3

Cl CH3
CH3
B

CH3

CH

CH3

CH3

CH3

Cl

CH3

CH3

The order of dipole moment amongst methyl halides is

A
B
C
D

33

CH3Cl
CH3Cl

CH3Cl
32

CH3 I > CH3 Br > CH3 Cl > CH3 F

CH3 F > CH3 Cl > CH3 Br > CH3 I
CH3 F > CH3 Br > CH3 I > CH3 Cl
CH3 Cl > CH3 F > CH3 Br > CH3 I

The lowest boiling point amongst these compound is of

2bromo2methylpropane

bromopentane

bromobutane

2bromobutane

Corrected
34

Highest melting point is of

A

35

orthodichlorobenzene

para dichlorobenzene
D chlorobenzene

meta dichlorobenzene

Which of these reactions is not shown by alkyl halides?

A

36

B Nuleophillic substitution
D Elimination reactions

Nucleophillic Addition

Reaction with metals

Reaction of bromoethane with KCN produces

A

37

propanenitrile

ethanenitrile

ethylisocyanide

nitrate

propaneisonitrile

Which of these is NOT an ambident nucleophile

A

38

cyanide

nitrite

thiocyanate

The reaction of silver carboxylate with alkyl halide produces an

A

39

alkane

anhydride

ester

ether

The product for the following reaction will be

CH 3
C2H
H5

2Rbutan2ol

40

I + OH N

racemic butan2ol

S 2

2methylpropan2ol

2Sbutan2ol

Which of these compounds will favour the SN 2 reaction the most?

A

iodoethane

2methyl2iodopropane

chloromethane

iodomethane

41
What should be the solvent if the reaction of (2R)2bromobutane with KCN gives racemic 2
methylbutanenitrile?
A

DMSO

antimony pentafluoride

water

ethanol

42
The penta coordinated structure that the carbon has to pass through in the SN 2 pathway is termed a
transition state because
C

A it is a bulky structure
B it is highly reactive and exists for a very small interval
D it cannot be and hence has not been isolated
carbon is pentacoordinated and its valence is 4

Corrected
43
Assertion: More stable is the intermediate carbocation, faster is the SN 1 reaction.
Reason: More stable carbocation reacts faster.
A If assertion is false but reason is true.
B If the assertion and reason both are false.
C If both assertion and reason are true but reason is not the correct explanation of the assertion.
D If assertion is true but reason is false.
E If both assertion and reason are true and the reason is the correct explanation of the assertion.
44

The order of reactivity of the four isomeric bromobutanes in SN 1 reaction will be

A
B
C
D

45

CH3 CH2 CH2 CH2 Br

CH3 CH2 CH2 CH2 Br
CH3 CH2 CH2 CH2 Br
CH3 CH2 CH2 CH2 Br

< (CH3 )2 CHCH2 Br < CH3 CH2 CH(Br)CH3

< CH3 CH2 CH(Br)CH3 < (CH3 )2 CHCH2 Br
> CH3 CH2 CH(Br)CH3 > (CH3 )2 CHCH2 Br
> (CH3 )2 CHCH2 Br > CH3 CH2 CH(Br)CH3

< (CH3 )3 CBr

< (CH3 )3 CBr
> (CH3 )3 CBr
> (CH3 )3 CBr

The instrument used to detect and measure optical activity is

A

46

polarimeter

optometer

Nicol prism

spectrophotometer

What can be said with certainty for (+)butan2ol

A

B It rotates the plane of plane polarized light towards right.

It belongs to D family
C Its absolute configuration is R
D Its a racemic mixture

47
When ()-2-methylbutan1ol is heated with concentrated hydrochloric acid, it forms (+)-1-Chloro-2methylbutane. What can be said about the reaction?
A The reaction proceeds by SN 2 mechanism but there is no change at the stereocentre
The reaction proceeds by SN 2 mechanism and there is complete stereochemical inversion at the chiral centre
C The reaction proceeds by the SN i mechanism and there is complete retention due to same side attack
D The reaction proceeds by the SN 1 mechanism and there is complete stereochemical inversion at the chiral centre
B

48

Hydrolysis of optically active (+)-2-bromobutane proceeds through SN 1 mechanism. The product is

A

49

(+)-butan-2-ol

2methylpropan2ol

()-butan-2-ol

()-butan-2-ol

The major product in reaction of 2-bromopropane with sodium ethoxide is

A

50

2-ethoxypropene

propene

ethoxypropane

2-ethoxypropane

The major product obtained in the reaction of 2-bromobutane with sodium tert-butoxide is
A

2-methylpropene

2-(tert-butoxy)butane

but-2-ene

but-1-ene

51
A solution of (+) -2-chloro-2-phenylethane in toluene racemises slowly in the presence of small amount
of SbCl5 , due to the formation of
A

carbocation

free-radical

carbene

carbanion

Corrected
52

Which of the following has the highest nucleophilicity?

OH

A
53

N H2

The order of reactivities of the following alkyl halides for a SN 2 reaction is

A

54

CH3

B
D

RF > RBr > RCl > RI

RI > RBr > RCl > RF

RF > RCl > RBr > RI

RCl > RBr > RF > RI

An SN 2 reaction at an asymmetric carbon of a compound always gives

A a mixture of diastereomers
B an enantiomer of the substrate
C a product with opposite optical rotation
D a single steroisomer

55
The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH is
0 1 2 3 4 5 6 7 8 9
56

Which of these will show nucleophilic substitution by hydroxyl group most easily?
Cl

Cl

Cl

NO2
A

NO2

Cl
NO2

NO2

NO2

NO2

57 Assertion: Presence of N O2 at the meta position has no eect on reactivity of haloarene in the nucleophilic
substitution reaction
Reason: N O2 at meta position is an electron donating group.
A

If both assertion and reason are true but reason is not the correct explanation of the assertion.
B If assertion is true but reason is false.
C If both assertion and reason are true and the reason is the correct explanation of the assertion.
D If assertion is false but reason is true.
E If the assertion and reason both are false.
58

The predominant electrophilic substitution reaction on chlorobenzene takes place at

A

59

para

both ortho and meta

meta

ortho

2-methyl butanoic acid is formed by the reaction CHCl3 , NaOH and

A

60

Propene

Ethene

1-Pentene

2-Butene

CCl4 + KOH (excess) end product of the reaction is:

A

HCOOK

CO2

K2 CO3

C(OH)4

Corrected
61

Nitrochloroform is prepared by the action of chloroform and:

A Hot concentrated nitric acid
Hot aqueous solution of NaNO2

B
D

Hot aqueous solution of KNO3

Hot dilute HCl + aq. NaNO2 solution

O
62

CH3 MgBr + CH2

A

CH3

CH2

CH

H O

H 2 product(major) is

CH2

CHO

none is correct

CH2

CH

CH

CH

CH3

OH

OH
D

CH2

CH3
63

Which is incorrect about Hunsdicker reaction?

A

64

The reaction proceeds through free radical

C Only Cl2 can give alkyl halide
For

I2 will give ester when treated with RCOOAg

D F2 cannot give alkyl halide

CH3 Br + OH CH3 OH + Br

The rate of reaction is given by the expression:

A

65

rate = k [CH3 Br][OH ]

Ethyl ether

Ethoxy ethene

All of these

Ethanol

All of these

Ethanol

Ethyl ether

Ethoxy ethene

Ethyl alcohol

Ethyl amine

Ethyl chloride

Ethane

Which of the following statement is wrong:

A

D
69

rate = k [CH3 Br]

The compound added to chloroform to remove phosgene is

A

68

When ethyl bromide is treated with dry Ag2 O, main product is:
A

67

rate = k[CH3 Br] [OH ]

D rate = k[OH ]

When ethyl bromide is treated with moist Ag2 O, main product is:
A

66

All carbonyl compounds of the general structure CH3 CO R give a positive iodoform test
B The only aldehyde giving iodoform reaction is acetaldehyde.
C All secondary alcohols give iodoform reaction
Alkanols of the structure CH3 CH(OH)R (where R = H, alkyl or aryl) give iodoform reaction.

Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH gives
A

p-cresol

Benzoic acid

o-cresol

2,4-dihydroxytoluene

Corrected
70
When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is mbromonitrobenzene. Statements which are related to obtaining the m-isomer are
A
C

Easier loss of H+ to regain aromaticity from the meta position than from otho and para positions.
B The electron density on meta carbon is more than on ortho and para position
The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least destabilized.
D Loss of aromaticity when Br+ attacks at the ortho and para position and not at meta position

71

(CH3 )3 CMgCl reaction with D2 O produces:

A

72

(CD3 )3 COD

(CD3 )3 CD

(CH3 )3 CD

Benzyl chloride (C6 H5 CH2 Cl) can be prepared from toluene by chlorination with:
A

73
group

SOCl2

NaOCl

SO2 Cl2

Cl2

Toluene, when treated with Br2 / Fe, gives p-bromotoluene as the major product, because the CH3

74

(CH3 )3 COD

deactivates the ring

activates the ring by hyperconjugation

D is para directing

is meta directing

The major product in the reaction

CH3 CH2 CH2 M gBr + CO

followed by hydrolysis is
A

Butanal

Butanoic acid

Butanaone

Propanal

75
The major product of reaction of excess methyl magnesium bromide with methyl methanoate followed
by hydrolysis is
A
76

acetaldehyde

isopropyl alcohol

acetone

tert-butyl alcohol

If CCl4 is used in Reimer Tiemann reaction, the final product obtained is

A

77

Salicylaldehyde

p-hydroxybenzoic acid
D Salicylic Acid

p-hydroxybenzaldehyde

What would be the final product for the following reaction sequence
benzaldehyde

bromobenzene + M g/ether A B
H+

red P/HI

B C D
A

bisphenylmethanol

Toluene

Benzyl alcohol

Match the reaction in Column I with the mechanism in Column II

bisphenylmethane

Corrected
Column I
CH3 CHBr CD3 on treatment with
alc. KOH gives CH2 = CH CD3
as a major product.
B P h CHBr CH3 reacts faster than
P h CHBr CD3
C P h CH2 CH2 Br on treatment with
C2 H5 OD/C2 H5 O gives P h CD = CH2
as the major product.
D P hCH2 CH2 Br and P hCD2 CH2 Br
react with same rate.
78 A P Q R S
A

79

B P Q R S

80

C P Q R S

81

D P Q R S

Column II
E1 reaction

E2 reaction

E1CB reaction

First order reaction