QB-HC-1

HC

1.

Which of the following alkene, has the slowest rate of the hydrogenation?
C C C

C (III)

C (I)

(II)

(A) I (C) III

(B) II (D) IV

2.

The organic compounds A and B are obtained by subjecting 1 butene to HBO and OMDM, respectively.  (HBOHydroboration  oxidation and OMDM oxymercuration demercuration). A and B can be distinguished by (A) Iodoform test (B) Fehling solution test of the dehydrogenated products of A and B (C) Tollen s reagent test of the dehydrogenated products of A and B (D) All the three tests : A, B and C

3.
OH H CH3
E
2

P
S

Br

N2

(Optically active)

The correct statement about the products of the two parallel reactions is: (A) The product P is optically inactive due to internal compensation while Q is optically inactive due external compensation. (B) The product P is racemic mixture while Q is a meso compound (C) Both P and Q are achiral molecule and hence optically inactive (D) Both P and Q are optically active. 4. A mixture of methane, ethylene and acetylene gases are passed through a woulf bottle containing ammonical Cu2Cl2 . The gas coming out is (A) Methane (C) Methane and ethylene 5. (B) Acetylene (D) The original mixture

A 10 gm mixture of butane and 2butene reacts with 8.0 gm of bromine dissolved in CCl4 . Calculate the percentage of butane in the mixture (A) 72% (C) 50% (B) 28% (D) 68%

(IV)

QB-HC-2

6.

1butene subjected to HBO and OMDM separately will yield products that can be distinguished by

(A) Tollends reagent test after subjecting the products to dehydrogenation (B) Iodoform test (C) Fehling solution test after subjecting them to dehydrogenation (D) All the three 7. In the reaction
M  |  t p Br p
Na  liq. NH

the product P is: (A) A pure compound which is optically inactive due to internal compensation (B) A binary mixture which is optically inactive due to external compensation (C) A binary mixture which is optically active (D) A pure compound which is optically inactive due to absence of chiral reaction 8. Arrange the CH bonds labelled 1, 2, 3 and 4 in the molecule (given below) in increasing order of their ease for homolytic fission.
H H H 3 3 2 H 2 H 1 H CH3

(A)

3 1

(C) 4 1 2 3 9. The compound with the highest boiling point is: (A) n- Hexane (C) 2,2- Dimethyl propane

10.

The maximum number of isomers for an alkene with the molecular formula C4H8 is: (A) 2 (C) 4 (B) 3 (D) 5

11.

The compound 1,2- butadiene has: (A) Only sp - hybridised carbon atoms (C) Both sp - sp2 hybridized carbon atoms (B) Only sp2- hybridized carbon atoms (D) sp, sp2 and sp3 - hybridized carbon atoms

r or mixt r )

(B) 1 3 (D) 2

4 1 3

(B) n- Pentane (D) 2- Methyl butane

QB-HC-3

12.

When propyne is treated with aqueous H2SO4 in presence of HgSO4 the major product is (A) Propanal (C) Propyl hydrogen sulphate (B) Acetone (D) Propanol

13.

In the following reaction

3 3 CH3  CH ! CH2 A B p p

A and B are,
H3C

(A)
H3C

B , 3

H3C CH3 O CH3 O B , 3 H3C CH3

(B)

H3C

CH2

CH2

B , 3

(C)

H3C

CH2

CH2

H3C

O B , H3C CH3

(D)
H3C

14.

Addition of hypochlorous acid to propyne gives

(A)

Cl2HC H

(C)

H3C CHCl2

15.

Which of the following dienes is expected to have least value of enthalpy of hydrogenation? (A)
H2C CH2

H2C

(C)
CH3

CH2

BH

CH C

H3C

Cl

(B)

H3C

Cl H3C OH Cl HO

(D)

Cl

(B)

CH2 H2C

(D)

H2C

CH2

QB-HC-4

16.

The alkene C7H12 producing CH3 (A) Hept-3-ene (C) Cycloheptene

O || C (CH2)4

O || C

H on ozonolysis is

(B) Hept-1-ene (D) 1-methyl cyclohex-1-ene

17

O
h ! NBS 3CH3 p x 1 qal p Y. Y is CH i nt

Br

(A)

Br

(C)

Br

18.

H3C OH
HBr p X, X is

H3C

Br OH

(A)

H3C

(C)
OH Br

19.

The catalytic hydrogenation is more easier in case of which alkene?

H3 C H3 C CH2 H3 C H3 C CH3 CH3 H CH3 CH3

(A)

(C)
H CH3

20.

H 2C

CH3

CH3

Which is not true about the above alkene? (A) It is not capable to show geometrical isomerism. (B) It is optically active and on hydrogenation it produces optically inactive product.

Br

(B)

CH3

(D)

Br

CH3

H3C

(B)

Br

H3C

Br OH

(D)

(B)
H H3 C

(D)
H3 C

QB-HC-5

(C) On treatment with hot acidic KMnO 4 it produces resolvable acid. (D) On treatment with HOBr it produces 1 bromo 3 methyl 2 pentanol. 21.
H3 C CH3
(major )

CH3 CH3
Cl

(A)

H 3C HO OH

(C)

H 3C Cl

22.

H3 C H

H
4

CH3

Which is true about the above reaction? (A) Bromine addition take place in syn manner (B) Product is optically inactive due to external compensation (C) Addition take place via free radical formation (D) Product is optically inactive due to internal compensation 23. Which of the following alkene has the lowest heat of hydrogenation?
H H
CH2

(A)
H H

H3C

(C)
H3C H

24.

What will the correct product (A) and (B) respectively of the following reaction?
R

H2 ( 1 le) p Ni (200-300)

Br2 (1 mol ) (B)

2 p CCl

Br


Cl

EtOH HOCl Alk n p p KOH, (

 

(B)
OH

(D)

H 3C O Cl

(B)
H

CH3 H

CH3 H

(D)
H3C



QB-HC-6
R H H H R Br , Br
R Br R Br H R H H R Br Br , , H

R R H Br , Br

(A)

(B)

(C)

(D)

25.

Which of the following will be the correct product (P) of the reaction
H 3C CH2
NBS P ? p

(A)

Br H3 C
Br

(B)

H 3C Br

CH2

(C)
H 3C CH2

(D)

Br CH2

26.

E R  C | C  R Rate ! r1 p


E R2C ! CR2 Rate ! r2 p

The relation between r1 and r2 if R is an alkyl group is: (A) r1 = r2 (C) r1 " r2 (B) r1 ! (D) r1
1 r2 2

r2

27.
O3 / Zn p ( ) H O
2

O H3C

. ( ) is
H

(A)
CH3 CH3

(B)
CH3 CH3

(C)
CH3

(D)

QB-HC-7

28.

H / KMnO 4 3 (B) n ( ) p (B) H O (

2

O .Zn

Structure of (A) is likely to be

H3C CH3 CH3 CH3 CH3 CH3 CH3

(A)
H3C CH3

(B)

H3C

(C) None of the above

(D) Both the above

29.
H2 C Cl

Cl

H3 C p
Cl

HCl H2 O2

The intermediate likely to be involved in this reaction is: (A)

H3C Cl Cl

(B)

H2C Cl

(C)

H2 C Cl

(D)

H3C Cl

H3C Br CH
H3C

(A)
H H C 6 H5 CH3

(C)
H5 C6 C6 H5

31.

HBO, OMDM and acid catalysed hydration will give same product in (A) (B)

H3C

(C)

 
H H
alcoholic KOH A. A is p E
2

30.

CH

 
C 6 H5 H3C C6 H5

(B)
H5 C6 H

(D)

None is correct

CH2

CH2

CH3

(D)

QB-HC-8

32.

The ozonolysis of 1,2dimethyl benzene i.e. o xylene gives (B) Methyl glyoxal (D) All the three above

(A) Glyoxal (C) Dimethyl glyoxal

33.

Match the LIST  X with LIST  Y LIST  X (Reactants)

F
et anolic p KOH

LIST  Y(Major Product) / Mechanism Hoffmann product with 3E hydrogens

(A)
H3C

E1CB

(A)

CH3 CH3

(B)

ethanolic p KOH

Saytzeff product

E1

(B)

CH3

(C)

H3C Cl H3C CH3 CH3 H

Pot. tert p Butoxide

Hoffmann product with 2E hydrogens

E1CB

(C)

(D)
H3C CH3

Cl

ethanolic KOH p

Hoffmann product with 4E hydrogens

E1

(D)

(A) AC, BA, CB, DD (C) AC, BA, CD, DB 34. Match LIST  X with LIST  Y LIST  X (A)
CH2
BH / THF
2 2

(B) AD, BC, CA, DA (D) AA, BB, CD, DB

LIST  Y (A) Alcohol which has six membered ring

3 p H O / OH

(B)

CH2

2 4 p

dil. H SO

(B) Alcohol which can undergo reaction with NaOI to give yellow ppt.

(C)

CH2

Hg(OAc )2 THF p NaBH

4

(C) Alkane

(D) (A) AC BA CD DC (C) AA BB CD DC

CH2

BH3 / THF p CH COOH

3

(D) Alcohol which will undergo reaction with pcc. (B) AD BA CB DC (D) AD BA CD DC

QB-HC-9

35.

The order of stability of the alkenes

R 2C ! CR 2
(1)

R 2C ! CHR
(2)

R 2C ! CH2
(3)

RCH ! CHR
( 4)

RCH ! CH2
(5)

(A) 1 " 2 " 3 " 4 " 5 (C) 1 " 2 " 4 " 3 " 5 36.

(B) 1 = 2 " 3 " 4 " 5 (D) 5 " 4 " 3 " 1 " 2

The most reactive alkene towards the addition of HBr is

CH3 CH3

(A)
OH CH3

(B)
O 2N

CH3

(C)
HO

(D)

CH3

37

H3C CH3 CH2

p
NaBH 4

RO  / Hg 2  / H

CH3

CH3

(A)

H3C CH3 CH3 O

(B)

H 3C CH3 OR

CH3

CH3

CH3

(C)

H3C CH3 OH

(D)

H3C CH3 OR

38.

When acetylene is passed through conc. solution of Cu2Cl2 and ammonium chloride containing some dil HCl and the substance formed reacts with dil HCl at 160rC, if forms another substance which then polymerizes. The polymer formed is (A) Benzene (C) Neoprene (B) Polyisoprene (D) PMMA

39.

Arrange (I) CH2 = CH - CH3, (II) CH2 = CH - C6H5, (III) CH 2 = CH - Cl in increasing order of ease of cationic polymerization. (A) III < II < I (C) III < I < II (B) I < II < III (D) II < I < III

40.

In the reaction sequence

QB-HC-10
Br

Product will be (A) cis alkene (C) mixture of cis and trans alkene 41. In the reaction sequence
CH3 I ( i ) BH 3 CH3  CH ! CH2 p[ x ] will be
( ii ) CH 3 COOH

(A) 2-methl propane (C) 2- methyl -2- propanol

42.

H
KNH 2 p . (

Br

Ph

H
Ph

(A)
Ph Ph O H

(C)
Ph OH

43.

Which among the following compound will give 1,4-addition reaction (A)
CH2 H2C
CH3

(C)

H2C O

44.

In the reaction sequence

CH 2I2 Zn CH3 CH = CH CH3 /  Cu p( )

! "

H3 C

C H

(B) trans alkene (D) mixture of diastereomers

(B) 2- methyl propanone (D) 2- methyl propanal

will be

(B)
Ph

Ph

Ph

(D)
H Br

(B)

H2C

CN

(D)

All of these

# $

" !

H C

CH3

alc KOH . p C6H5 (CH3 )C ! C(CH3 )C H

% %

QB-HC-11

X will be (A) 2-methylbutane derivative (C) Cyclopropane derivative 45. In the reaction sequence (B) Pentane derivative (D) All of these

H3C H3C

O O O

CH3 H
4 p ro

NaBH

ct will be

H3C

CH3 an O H3C CH2 H3C CHO

(C)
H3C

OH an

H3C OH

(D)

an

46.

Which among the following compounds are reduced by Na/NH3(l)

H3C
CH3

(A)
CH3

(B)

(C) 47

H2C CH2

(D)

All of these

In the reaction sequence

H3C CH2
SeO 2 p( )

X will be
OH OH

(A)
CH3 OH

(B)
H 3C

CH2

OH

(C)

HO

CH2

(D)
H3C CH3

48

Consider the reaction:

H P

HCl p P

CH2

The product P is:

&

H3C

&

(A)

(B)

CH3COOCH3 and CH3COOH

H2C

CH2

&

'

P Cl

(A)

H Me (d-for )

(B)

Cl Me (l-for )

(C)

An equi molecular mixture of (A) (D) and (B)

CH2Cl

49.

Identify Z in the following reaction sequence:

CH2 H3C
C2 HBr / Peroxide p H5 ONa p et er

(A)

CH3 H3C

(B)

H3C

CH3

(C)
CH3

CH3

(D)

CH2 H3C

50.

Which of the following will undergo faster dehydro-bromination?

Br Br

(A)

(B)

Br

Br

(C)

(D)

51.

Which of the following carbides on hydrolysis gives propyne? (A) Be2C (C) CaC2 (B) Al4C3 (D) Mg2C3

52.
O 2N C CH3
O O
Hg / H p P, P is :
2 

(A)

O2 N H3C

(B)

O 2N CH3 O

(
H

QB-HC-12

CH3

QB-HC-13

(C)

O 2N O H3C

(D)

None of these

53.

H /( ( ) p

CH3 H3C

3 p( Y ). ( ) and ( Y ) are

H O

( ) isomers (C) eit er ( ) or (B) 54.

NaOMe CH2O p( )  (B ) . ( ) and (B) are MeOH

(B) identical (D) neit er ( ) nor (B)

( ) HCO2Me and CH 3OH (C) HCO2H and CH 3ONa+

(B) HCO2Na+ and CH3OH (D) HCO2H and CH 3OH

HI p( A ). ( A ) is

55.
H3C CH3

(A)

H3C I

CH3

(B)

H3C I

CH3

(C)
H3C CH3

(D)

I H3C