Cls Jeead-17-18 Xi Che Target-4 Set-2 Chapter-13

Chapter 13
Hydrocarbons
Solutions
SECTION - A
Objective Type Questions (One option is correct)
1. The minimum number of carbon atoms in alkane molecule to show chain isomerism is
(1) 2 (2) 3 (3) 4 (4) 5
Sol. Answer (3)
Butane can form n-butane and isobutane.
2. Alkanes can be iodinated in the presence of

(1) HI (2) I2 and P (3) I2 + HIO3 (4) PI3
Sol. Answer (3)
HIO3 and HNO3 being oxidants oxidize HI and prevent the backward reduction of RI.
3. In the complete combustion of hydrocarbon (CnH2n+2) the number of oxygen molecules required per mole of
hydrocarbon is
n (n  1) (3n  1) ⎛ 1⎞
(1) (2) (3) (4) ⎜ n  ⎟
2 2 2 ⎝ 2 ⎠
Sol. Answer (3)

3n  1
CnH2n 2  O2  nCO2  nH2O (Eudiometric equation)
2
4. Highest boiling point is expected for

(1) 2, 2-dimethyl butane (2) 2, 3-dimethyl butane (3) 3-methyl pentane (4) 2-methyl pentane
Sol. Answer (4)
Due to largest surface area.
5. (CH3)3CMgCl on reaction with D2O produces

(1) (CH3)3CD (2) (CH3)3COD (3) (CD3)3CD (4) (CD3)3COD
Sol. Answer (1)
(CH3)3 CMgCl + D2O  (CH3)3CD + MgODCl
Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
98 Hydrocarbons Solutions of Assignment (Set-2)
6. Consider the folllowing reaction

CH 3 CH CH CH3 + Br X + HBr
D CH 3

Identify the structure of the ( X )
(1) CH 3 CH CH CH2 (2) CH3 CH C CH3

D CH3 D CH3
(3) CH3 C CH CH3 (4) CH3 CH CH CH3
D CH3 CH3
Sol. Answer (2)
The reaction proceeds in a direction to give most stable free radical as reaction intermediate.
7. In the given reaction

O
x
CH3 C C2H5  CH3 CH2 C2H5
‘X’ will be
(1) LiAlH4 (2) NaBH4
_
(3) BCl3SnH (4) NH2 NH2 OH , glycol
Sol. Answer (4)
It is Wolff-Kishner reduction.
8. 2.8 g of pure alkene containing only one double bond per molecule, reacts completely with 8 g of bromine in
an inert solvent. The molecular formula of alkene is
(1) C2H4 (2) C4H8 (3) C3H4 (4) C6H12
Sol. Answer (2)
C4H8  Br2  C4H8Br2
2.8 gram 8 gram 10.8 gram
∵ 8 g Br2 reacts with 2.8 g alkene

2.8  160 g
160 g Br2 reacts with = g alkene = 56 g alkene
8
Hence alkene is C4H8
9. Consider the following statements : a hydrocarbon of molecular formula C5H10 may be

(I) Mono-substituted alkene
(II) di-substituted alkene
(III) tri-substituted alkene
Which of the above statements are correct?
(1) I, II and III (2) I and II but not III (3) II and III but not I (4) I and III but not II
Sol. Answer (1)
CH3  CH2  CH2  CH 
CH2 CH3 – CH  CH – CH2 –CH3
monosubstituted disubstituted
CH3 — C CH — CH3
CH 3
Trisubstituted
with respect to presence of alkyl groups.
Solutions of Assignment (Set-2) Hydrocarbons 99
10.
The most suitable sequence of reagents to perform this conversion is

(1) HBr then (CH3 )3 COK /(CH3 )3 C  OH (2) NBS then alcoholic KOH
(3) HBr–peroxide then CH3 CH2OK / CH3 CH2OH (4) HBr–peroxide then (CH3 )3 COK / (CH3 )3 COH
Sol. Answer (4)
HBr (CH3)3COK
Peroxide Br
11. The compound having only primary hydrogen atoms is

(1) Isobutene (2) 2, 3-dimethyl butene-2 (3) Cyclohexane (4) Propyne
Sol. Answer (2)
CH 3 CH3
C=C It contains only primary hydrogen
CH3 CH3
12. Which equation does not represent an example of Friedel-Crafts reaction?

AlCl3
(1) C6H6  C2H5Cl (  C6H5C2H5  HCl
Anhy )
ZnCl2
(2) C 2H5 OH  HCl   C 2H5 Cl  H2O
AlCl
(3) C 6H6  CHCl3 
3
(C 6H5 )3 CH
( Anhy )
Anhy
(4) C6H6  CH3CH2COCl  C 6H5 COCH2CH3  HCl
AlCl3
Sol. Answer (2)

Friedel Crafts alkylation involve conversion of Arene into alkyl arene in the presence of acids (Lewis acid as
mineral acid). But in example (2). Alkyl halide is obtained from alcohol.
13. In the reactions,
CH2 CH2 OH
   M 
Hypochlorous R
CH2 acid CH2 OH

M and R are respectively
(1) CH3 CH2Cl and NaOH (2) CH2Cl  CH2OH and aq NaHCO3
CH2 CH2
(3) CH3 CH2OH and HCl (4) and heat
O
Sol. Answer (2)
CH 2 HOCl CH2OH Aq NaHCO3 CH2–OH

CH2 CH2Cl CH2–OH
14. Arrange the following compounds in increasing order of reactivity towards the addition of HBr
CH2
RCH CHR , , R 2C CHR , R2C CR2
CH2
CH2
(1) < RCH CHR < R2C CHR< R2C CR2
CH2
(2) R 2C CHR < RCH CHR < CH2 CH2< R2C CR2
(3) R 2C CR 2 < R2C CHR < RCH CHR < CH2 CH2
(4) R2C CR2< CH 2 CH2 < RCH CHR < R2C CHR
Sol. Answer (1)
Due to formation of most stable carbocation.
15. Among the following compounds, the decreasing order of reactivity towards electrophilic substitution is
CH3 O CH3 CF3

I II III IV
(1) III > I > II > IV (2) IV > I > II > III (3) I > II > III > IV (4) II > I > III > IV
Sol. Answer (1)
OCH3 CH3 CF3
> > >

+ M effect Hyperconjugation – I effect
Me
⎡ ⎤
N
⎢n-Bu

Me⎥

16. OH 
⎣ Et ⎦
The alkene formed as a major product in the above elimination reaction is
CH2 Me Me
(1) (2) (3) (4)
CH2
Sol. Answer (2)
OH
H (More acidic)
CH3
CH2 CH2
N H (Less acidic)
CH2 CH CH CH
CH3
N
CH2 CH2 CH2 CH
17. HBr reacts with CH2 at room temperature to give

II
CH OCH3
(1) CH3 CHO and CH3OH (2) BrCH2CHO and CH3 OH
(3) BrCH2 CH2 O CH3 (4) H3C CHBr OCH3

Sol. Answer (4)
MeO CH CH 2 MeO CH CH 3
H Br
Br
MeO CH CH3
Br
18. Colouration of Br2 / CCl4 will be discharged by
CH = CH – COOH COOH
(1) (2)
Cinnamic acid Benzoic acid
O
COOH
(3) (4) C – CH3
COOH
Phthalic acid Acetophenone
Sol. Answer (1)
CH CH—C—OH
It is an unsaturated acid hence shows addition with bromine
19. CH2 CH CH CH2 

Zn, CH3OH
  Product
Br Br
The predominating product is
(1) (2) CH2 C C CH2 (3) CH 2 CH CH CH 2 (4)
Sol. Answer (3)

Br
CH2 CH CH CH2
Br
Zn
CH 2 CH CH CH2 + ZnBr 2
(i) O3/(CH3)2S
20. (ii) H2O/Zn
product
The ozonolysis product is

COCH 3
CHO CH3 CO CHO
(1) (2)
CHO
O O
(3) H C CH3 (4) H C C CH3

O
Sol. Answer (2)
O3
Zn – H2O
O
CHO
21. Consider the following reaction
CC
Na/NH3
H
C=C
H
The reactive intermediate involved in this reaction is

(1) Carbanion (2) Carbocation (3) Free radical anion (4) Free radical cation
Sol. Answer (3)
R
R C C R C C
e R
(Radical anion) – a reactive intermediate
22. Most probable product of the addition of one molecule of Br2 on Hexa-1, 3, 5-triene is
(1) Br — CH2 — CH CH — CH CH—CH2Br (2) CH2 — CH — CH — CH — CH — CH2
Br Br
Br
(3) CH2 — CH — CH — CH — CH — CH2 (4) CH — CH2 — CH — CH — CH — CH
Br
Br Br
Sol. Answer (1)
Conjugated diene is more stable than isolated or cumulated dienes.
23. The intermediate during the addition of HCl to propene in the presence of peroxide is
 
(1) CH3 — C H — CH2Cl (2) CH3 — C H — CH3
 
(3) CH — CH — C H (4) CH — CH — C H
3 2 2 3 2 2
Sol. Answer (2)

As HCl does not give peroxide effect the reaction of HCl even under the presence of peroxide proceeds through
ionic mechanism.
Cl
 Cl
CH3 – CH = CH2 CH3 – CH – CH3 CH3 – CH – CH3
reactive
H – Cl
intermediate
24. Which of the following compound is most reactive towards an electrophile (E+)?
(1) (2) (3) (4)
Sol. Answer (1)



E E
most stable
benzyl carbocation
Other unsaturated compounds give less stable reactive intermediate when treated with electrophile.
25. The reaction

CH3 CHBr — CH2Br  2KOH(alc )

 CH3 C  CH  2KBr  2H2O is called
(1) Dehalogenation (2) Dehydrohalogenation (3) Decarboxylation (4) Dehydration
Sol. Answer (2)
Removal of Br and H from  &  carbon is called dehydrohalogenation
26. Compound A (i) decolourises Baeyer’s reagent (ii) on hydroxylation and further oxidation with KMnO4 gave formic
acid and acetone (iii) on ozonolysis gave one molecule of acetone and one molecule of formaldehyde. A is
(1) Propylene (2) Ethylene (3) n-Butylene (4) iso-Butylene
Sol. Answer (4)
H3C H3C H
(i) O 3
C = CH2 (ii) Zn – H 2O
C = O+ O= C
H3C H
H3C
isobutylene (A)
KMnO4 ,

CH3
Give +ve test with
Baeyer's reagent HCOOH + O = C
CH3
27. Which of the following alkene on acid catalysed hydration form 2-methyl propan-2-ol ?
(1) (CH3)2C CH2 (2) CH3 — CH CH2
(3) CH3 — CH CH — CH3 (4) CH3 — CH2 — CH CH2
Sol. Answer (1)

H H
H O OH
H O H –H
H3C C CH2 H3C C CH3 H3C C CH3 H 3C C CH3
CH3 CH3 CH3 CH3
28. The reaction of chlorine water with propene gives
(1) ClCH2 — CH(OH)CH3 (2) CH2(OH)CH(Cl)CH3
(3) ClCH2CH2CH2OH (4) ClCH(OH)CH2CH3
Sol. Answer (1)

Cl2/H2O
CH3 – CH = CH2 CH3 – CH – Cl2
OH Cl
29. The reaction of one equivalent of HBr with H2C CH — C CH at relatively high temperature gives which
of the following as major product?
(1) CH2 CH — CBr CH2 (2) CH3 — CHBr — C CH
(3) CH2 CH — CH CHBr (4) CH3 — CH2 — C C — Br
Sol. Answer (1)
HBr
CH2 = CH – C  CH CH2 = CH – C = CH2
Br
Conjugated diene
30. Point out A in the given reaction sequence
O3/H2O2 
A B 2CH 3COOH + CO 2
(1) (2) (3) (4)
Sol. Answer (3)
O3 COOH 
2CH2 2CH3COOH + 2CO2
H2O2 COOH
31. In the following reaction,
O
conc. HNO3
N X
H conc. H2SO4
the structure of the major product ‘X’ is [IIT-JEE-2007]
O2N
O O
(1) (2)
NO2
N N
H H
O O
(3) (4)
N O2N N
H NO2 H
Sol. Answer (2)
O
N
1
H 2
Ring 1 is activated by NH group
32. The reagent(s) for the following conversion. [IIT-JEE-2007]
?
Br H H
Br
is/are
(1) Alcoholic KOH (2) Alcoholic KOH followed by NaNH2
(3) Aqueous KOH followed by NaNH2 (4) Zn/CH3OH
Sol. Answer (2)
33. The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne.
The bromoalkane and alkyne respectively are [IIT-JEE-2010]
(1) BrCH2CH2CH2CH2CH3 and CH3CH2C  CH (2) BrCH2CH2CH3 and CH3CH2CH2C  CH
(3) BrCH2CH2CH2CH2CH3 and CH3C  CH (4) BrCH2CH2CH2CH3 and CH3CH2C  CH
Sol. Answer (4)

Br
CH2—CH2—CH2 —CH3
NH2
CH3—CH2—CC—H CH3—CH2—CC CH 3—CH2—CC—CH2—CH 2—CH2—CH 3
3-octyne
34. The compounds P, Q and S
O
COOH OCH3
C
O
HO H3C
P Q S
were separately subjected to nitration using HNO3/H2SO4 mixture. The major product formed in each case
respectively, is [IIT-JEE-2010]
O O
COOH OCH3 COOH OCH3
C C
(1) O (2)
HO H3C O
HO NO2 H3C
NO2 NO2 O2N NO2 NO2
O NO2 O
COOH OCH3 COOH OCH3
C C
(3) O (4) O NO2
HO H3C NO2 HO H3C NO2
NO2 NO2
Sol. Answer (3)

COOH COOH
HNO3/H2SO4
HO HO
NO2
OCH3 HNO3/H2SO4 OCH3
H3C H3C NO2
O O NO2
C HNO3/H2SO4
C
O O
35. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure.
and and
(I) (II)
(III)
The correct order of their boiling point is [JEE(Advanced)-2014]
(1) I > II > III (2) III > II > I (3) II > III > I (4) III > I > II
Sol. Answer (2)
As branching increases boiling point decreases, so order of boiling point is III > II > I.
36. In the following reaction, the major product is
CH3
CH2 [JEE(Advanced)-2015]
1 equivalent HBr
H2C
CH3 CH3
CH3 CH3 CH3
(1) H2C (2) H C (3) Br
(4) Br
3
Br H2C H3C
Br
Sol. Answer (4)
CH3
CH2 1 equiv. HBr –
Br
 Br
H2C H
+
H3C 
(Major)
SECTION - B
Objective Type Questions (More than one options are correct)
1. Which of the following alkanes will give more than one monochloro product?
(1) (2) (3) (4)
Sol. Answer (1, 2, 4)

Only in neopentane all H’s are equivalent. Therefore it will give only one monochloro derivative. Other alkane
will give more than one monochloro derivatives.
2. Which of the following name reaction is used to prepare alkane containing new carbon-carbon bond?
(1) Wurtz reaction (2) Corey House synthesis
(3) Sabatier and Senderns reaction (4) Clemmensen’s reduction
Sol. Answer (1, 2)
Sabatier – Sanderen’s reaction forms alkene to alkane with same number of C-atoms
Clemmenson reduction is for aldehyde and ketone to form alkane with same number of C-atoms
3. In which of the following cases product will contain more number of carbon atoms than do present in reactant
molecule?
R R'
(1) C C + H2 A heat
(2) RCOOK + OH–   B
H H CaO
(4) RX  Na     D
Electrolysis dry ether
(3) RCOOK  H2O    C
Sol. Answer (3, 4)
H2O
R – COOK R–R
electrolysis
Na
R–X R–R
ether
4. The photochemical chlorination of paraffins occurs by a free radical mechanism. From the following set of
reactions, pick out the chain propogation steps
h
(1) Cl2   2 Cl (2) CH4  Cl  
  CH3  HCl
(3) H3 C   Cl2  H3 C — Cl  Cl (4) Cl   Cl   Cl

2
Sol. Answer (2, 3)
Steps where one free radical is converted to another free radical are known as propagation steps.
5. The concentrated aq. solution of pottasium salts of acetic acid and propanoic acid are electrolysed. Which
of the following are produced?
(1) CH3CH2CH2CH2CH3 (2) CH3CH2CH2CH3 (3) CH3CH2CH3 (4) CH3CH3
Electrolysis
H3C – COOK + CH3 – CH 2 – COOK CH 3 – CH 3 + CH 3 – CH 2 – CH 3 + CH 3 – CH 2 – CH 2 – CH 3
6. Predict the product of given reaction
CH3 H CH2N2
C—C  
H H
CH3 H
(1) CH3CH2CH2CH3 (2) C—C
H H
C
H2
CH3 H CH 3 — CH2 H
(3) C—C (4) C C
H CH2 — H H H
CH2N2 cannot change unsaturation.
7. Which of the following reagents on reaction with acetylene yield same product?
(1) O3/H2O + H+ (2) KMnO4/OH–/H2O (cold) (3) SeO2 (4) O3 + H2O/Zn
O3/H2O COOH
HC CH +
H COOH
–
KMnO4/O H /H2O(c old) CHO
or CHO
SeO2
or
O3/Zn–H2 O
8. In which of the following case product of oxidative and reductive ozonolysis is/are different?
R R R'
(1) C CH — R (2) C6H10 (Cyclohexene) (3) CH2 CH2 (4) C C
R R'' R'''
R O /Zn–H2O R
C = CH – R 3 C = O + R – CHO
R R
O3/H2O R
C = O + R – COOH
R
O 3/Zn – H2O CHO

CHO CH2 = CH 2 2HCHO
,
O 3 / H2 O COOH 2HCOOH
COOH
9. Structures of -complex formed during nitration of Anisole would be
OMe OMe OMe OMe

H
H
(1) NO2 (2) (3) (4)
NO2 H NO2 H NO2
Sol. Answer (1, 3)
As MeO – group is ortho-para director the problable -complexes in electrophilic substitution of anisole are
OMe
ortho attack
 
of E
OMe E
H
OMe
para attack
of electrophile

H
O2N
10. Which of the following reagents can be used to prepare 2-butyne by simple organic transformations?
Cl Cl Br
| | |
(1) (2) CH3 — C — C — CH3 (3) CH3CH2 — C — CH3 (4) CH3 — CCl3
| | |
Cl Cl Br
No elimination is possible in
11. Which of the following will give Acetophenone as major product when treated with Benzene and AlCl3?
O O O
(1) Ac2O (2) CH 3 — C — NH 2 (3) CH 3 — C — Cl (4) CH3CH2 — C — Cl
Sol. Answer (1, 3)
O
Ac2O and CH3 – C – Cl will generate acylcarbocation with Lewis acid and hence acyl carbocation will give
acetophenone with benzene.
12. Alkenes give addition reaction with
(1) HCN (2) (BH3)2 (3) Br2 (4)
Sol. Answer (2, 3)

HCN is weak acid and cannot attack to alkenes
13. Friedel-Crafts alkylation is expected to proceed through carbocationic intermediate. What would be the alkylation
products when Benzene reacts with cyclopropyl chloride under the presence of anhydrous AlCl3?
Me
(1) CH2 (2) (3) (4)
Sol. Answer (2, 4)

+
Rearrangement 
CH2 = CH – CH2
14. Which of the following statements is/are correct regarding catalytic hydrogenation?
(1) It is an exothermic reaction
(2) It is syn addition
(3) Reactive intermediate is carbocation
(4) Reactive intermediate is free radical
Sol. Answer (1, 2 )
Hydrogenation follows true radical mechanism
15. For which of the following compounds degree of unsaturation is 3?
(1) (2) (3) (4)
Sol. Answer (1, 4)

Both can absorb 3 mole H2 to form a straight alkanes.
16. In the Newman projection for 2, 2-dimethylbutane [IIT-JEE-2010]
X
H3C CH3
H H
Y
X and Y can respectively be

(1) H and H (2) H and C2H5 (3) C2H5 and H (4) CH3 and CH3
Sol. Answer (2, 4)
X H3C CH3
H3C CH3
X C
C
H H H HY
Y
When X = H & Y = C2H5
H3C CH3
H C
2
C C2H5
H 1 H
2, 2- dimethyl butane
When X = CH3 and Y = CH3
H3C CH3
C2
4CH3
C CH3
H 3 H 1
2, 2-dimethyl butane
17. The reactivity of compound Z with different halogens under appropriate conditions is given below :
OH monohalosubstituted
derivative when X2 = I2
X2
dihalosubstituted
derivative when X2 = Br2
C(CH3)3
Z
trihalosubstituted
derivative when X2 = Cl2
The observed pattern of electrophilic substitution can be explained by [JEE(Advanced)-2014]

(1) The steric effect of the halogen (2) The steric effect of the tert-butyl group
(3) The electronic effect of the phenolic group (4) The electronic effect of the tert-butyl group
O–H
(I) (III)
(II)
(I), (II) and (III) are probable positions as per electronic effect of OH group where electrophile can attack and
due to steric hindrance at (II) and (III) positions bulky electrophiles are not preferred like I only preferred at
position I, Bromine at positions II and I while chlorine at all three positions.
18. Among the following, reactions(s) which gives (give) tert-butyl benzene as the major product is(are)
[JEE(Advanced)-2016]
Br
Cl OH
(1) (2) (3) (4)
NaOC2H5 AlCl3 H2SO4 BF3OEt2
Br
+
NaOEt
–
AlCl3 + 1, 2 H +
Shift
Cl
+
H +
BF3 1, 2 H
–
+
+
O–H Shift
H
19. The correct statement(s) for the following addition reactions is(are) [JEE(Advanced)-2017]
H3C H
Br2/CHCl3
(i) M and N
H CH3
H3C CH3
Br2/CHCl3
(ii) O and P
H H
(1) O and P are identical molecules
(2) (M and O) and (N and P) are two pairs of enantiomers

(3) (M and O) and (N and P) are two pairs of diastereomers
(4) Bromination proceeds through trans-addition in both the reactions

Sol. Answer (3, 4)
CH3 CH3
H3C H Br2/CHCl3 H Br Br H
(i) C=C +
H CH3 H Br Br H
Trans CH3 CH3
Meso (M and N)
CH3 CH3
CH3 CH3 Br2 H Br Br H
(ii) C=C +
H Br H H Br
H
Cis CH3 CH3
O P
Pair of enantiomers
Cis anti Racemic
M and N are meso (identical)
O and P are pair of enantiomers

(3) (M and O) and (N and P) are two pairs of diastereomer.
(4) Bromination proceeds through anti addition.
SECTION - C
Linked Comprehension Type Questions
Comprehension-I
If we see the reaction of methane with halogen, the rate determining step for chlorination is, endothermic
reaction of the chlorine atom with methane to form methyl radical and a molecule of HCl. So free radical is
the intermediate of the reaction. Formation of free radical depends upon the energy required to break a bond
between a hydrogen atom and a carbon atom. Chlorination of propane and Bromination of propane, when
compared it is found that bromination is more selective than chlorination. The probability factor for
3°, 2°, 1° H atom is 5.0 : 3.8 : 1.0 at 25°C for chlorination.
1. Isobutane when reacts with chlorine in presence of ultra violet radiations yield 2 products primary hydrogen
substituted and 3° hydrogen substituted. Find their % in product mixture
(1) 64%, 36% (2) 72%, 28% (3) 36%, 64% (4) 30%, 70%
Sol. Answer (1)
CH3
CH3 – CH – CH3
9 1
%1º product =  100 
64%
9 1 5
%3º Product = 100 – 64 = 36%
2. When the given compound is subjected to chlorination and Bromination, what are the major product, A and B
respectively?
Cl2 / h
A
Br2 / h
B
(1) (2) & Br

Cl & Br
Cl
& Br
(3) Cl & (4)
Br Cl
Sol. Answer (2)
Cl2/h
Its % formation is maximum
Cl
Br2/h
Br due to formation of most stable radical

 A  
 B.
2 Br Na
3. hv dry ether
Major product B is
(1) (2) (3) (4)
Sol. Answer (1)

Br
Br2
h
Comprehension-II
Addition of water molecule across double bond to yield Antimarkownikov’s product, can be accomplished by
Hydroboration followed by oxidation. Reaction follows as:
| | H C —C
C— C + BH3 —C—C—B
| | H
H
| | C —C | |
— C —C — B H — C —C — B
| | | |
H 2 H 3
H2O2/OH–
| |
—C—C—
| |
H OH
1. Product of hydroboration oxidation of 1-methyl cyclopentene is

(1) cis-1-methyl cyclopentanol (2) cis-2-methyl cyclopentanol
(3) trans-1-methyl cyclopentanol (4) trans-2-methyl cyclopentanol
Sol. Answer (4)
CH3
H OH
H = trans-2-methylcyclo pentanol
2. Which of the following statement is true about the given reaction?

(1) Hydroboration step of the reaction proceed through Markovnikoff’s addition
(2) The reaction is neither stereoselective nor regioselective
(3) It is stereoselective but non-regioselective
(4) Hydroboration step of the reaction proceeds through Anti-Markovnikoff’s addition
Sol. Answer (1)
Hydroboration step of the reaction proceeds through Markovnikoff’s addition, but the overall reaction gives
anti-Markovnikoff’s product.
3. BH3, is behaving as
(1) Electrophile (2) Nucleophile (3) Catalyst (4) Substrate
Sol. Answer (1)
BH3 is a Lewis acid (electrophile) due to incomplete octet.
Comprehension-III
-Farnesene is a terpene found in the oil of citronella, refer to the structure of -farnesene to answer the
following questions
1. How many stereoisomers are possible for farnesene?
(1) 2 (2) 4 (3) 8 (4) 16
Sol. Answer (2)
Farnesene has two stereocenters hence-four stereoisomers are possible.
2. If -fernesene is reacted with an excess of ICl. What would be the major product?
Cl Cl Cl Cl I
I I I
(1) (2) I (3) Cl (4)
I Cl I I I
I I
Cl Cl Cl I Cl I I Cl I
I I
I
Cl Cl I
Sol. Answer (1)
ICl  I  Cl , Cl– attacks on more stable carbocation.
3. One mole of farnesene will absorb ...... moles of H2 gas in the presence of Ni2B catalyst under normal conditions
(1) 0 (2) 2 (3) 4 (4) 6
Sol. Answer (1)
C=C are not hydrogenated under the presence of Ni2B or Lindlar’s catalyst.
Comprehension-IV
Hydration reaction of alkene is catalyzed by dilute acid. Selection of acid is important. Conjugate base of
the acid should not interfere in the reaction. There are other means by which alkenes can be converted to
alcohols. Oxymercuration demercuration gives Markovnikoff’s alcohol while hydroboration oxidation give
Anti Markovnikoff’s alcohol.
1. The reagent required to perform the given transformation is
CH2 CH2
OH
Ph Ph Ph Ph
(1) H2SO4/H2O (2) HCl/H2O

(3) Hg(OAc)2/H2O then NaBH4 (4) BH3/THF then OH/H 2O 2
Sol. Answer (3)
Oxymercuration-demercuration gives alcohol without rearrangement.
2. Which of the following reagent cannot be used to obtain product predominantly from the given reactants?
CH2 CH3
OH
(1) HBr/H2O (2) H2SO4/H2O
(3) H3PO4/H2O (4) Hg(OAc)/H2O then NaBH4
Sol. Answer (1)
Conjugate base of HBr is a strong nucleophile hence it interferes in the reaction.
3. When subjected to acid catalyzed hydration which of the following alkene will give rearrangement alcohol as the
predominant product?
CH2 Ph
(1) (2) (3) (4)

CH —
— CH2
O
Sol. Answer (1)
Ring expansion.
Comprehension-V
An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the
following sequence of ractions, in which Q is an intermediate organic compound. [IIT-JEE-2011]
(i) conc. H2SO4
(catalytic amount) O
(i) dil. H2SO4 / HgSO4 (–H2O)
P Q 2 C
(ii) NaBH4 /ethanol (ii) O3
(C6H10)
(iii) dil. acid (iii) Zn /H2O H3C CH3
1. The structure of compound P is

(1) CH3CH2CH2CH2 – C  C – H (2) H3CH2C – C  C – CH2CH3
H3C H3C
(3) H – C – C  C – CH3 (4) H3C – C – C  C – H
H3C H3C
2. The structure of the compound Q is
H3C OH H3C OH
(1) H – C – C – CH2CH3 (2) H3C – C – C – CH3
H3C H H3C H
H3C OH OH
(3) H – C – CH2CHCH3 (4) CH 3CH 2CH 2CHCH 2CH 3
H3C
Solutions of Comprehension-V
1. Answer (4)
2. Answer (2)
O (i) NaBH4 OH
H3C H3 C H3C
Hg2 +/H3O+ (ii) dil H
+
H3C C – C C–H H3C C – C H3C C – C – H

H3C H3 C CH3 H3C CH3
H3 C H H3C H
–H   H
C – C – CH3 H3 C C – C
H3 C CH3 H3C CH3
H3C CH3 (i) O3 CH3

(ii) Zn–H2O
C C 2 C O
H3C CH3 CH3
SECTION - D
Assertion-Reason Type Questions
1. STATEMENT-1 : Alkynes are more reactive than alkene towards HBr.
and
STATEMENT-2 : Alkynes have higher degree of unsaturation than alkenes.
Sol. Answer (4)
Alkynes are less reactive than alkenes towards electrophilic addition reactions.
2. STATEMENT-1 : n-pentane has higher boiling point than neopentane.

and
STATEMENT-2 : Larger surface area is responsible for greater van der Waal's force of attraction.
Sol. Answer (1)
Surface area deceases with increase in branching
3. STATEMENT-1 : Addition of HBr on CH2 = CH – NO2 follows anti-Markovnikoff's rule.

and
STATEMENT-2 : Electron withdrawing NO2 group destabilizes carbocation on the adjacent carbon.
Sol. Answer (1)
Question is self explanatory.
4. STATEMENT-1 : Nitrobenzene does not give Friedel-Craft reaction.

and
STATEMENT-2 : Nitro group is meta directing group.
Sol. Answer (2)
Nitro group is highly deactivating group
5. STATEMENT-1 : Hydroboration followed by oxidation of propene gives anti-Markovnikoff's alcohol.

and
STATEMENT-2 : Hydroboration reaction proceeds through Markovnikoff's addition.
Sol. Answer (2)
1st step is according to Markownikov’s rule
6. STATEMENT-1 : Anthracene and phenanthrene are isomers.

and
STATEMENT-2 : Anthracene and phenanthrene both have 14  electron each.
Sol. Answer (2)
&
are position isomers
7. STATEMENT-1 : Ethyne is stronger acid than ethene.

and
STATEMENT-2 : C–H bond in ethyne is formed by sp-sp overlap.
Sol. Answer (3)
Due to 50% s-character of triple bonded carbon hydrogen becomes acidic and C — H bond is formed by
sp-s linkage.
8. STATEMENT-1 : In Friedel-Craft’s acylation reaction multiple acyclation product is obtained.

and
STATEMENT-2 : Introduction of alkyl group activates benzene ring.
Sol. Answer (4)
Multiple alkylation is present in Friedel-Crafts alkylation not in acylation.
9. STATEMENT-1 : Vinyl chloride is more reactive than ethylene.

and
STATEMENT-2 : Addition of HBr on vinyl chloride follows Markovnikoff’s addition.
Sol. Answer (4)
Due to presence of electron withdrawing group vinyl chloride is less reactive than ethylene.
10. STATEMENT-1 : Benzyne reacts with 1,3-butadiene to give new six membered ring.
and
STATEMENT-2 : It is an example of Diels-Alder reaction.
Sol. Answer (2)
Both statements are correct.
11. STATEMENT-1 : Acid catalyzed hydration of (I) involves rearrangement .
and
STATEMENT-2 : The formed intermediate has potential for rearrangement.
Sol. Answer (1)
1, 2-Hydride
H shift
+H
H
12. STATEMENT-1 : Among isomeric pentanes 2, 2-dimethyl propane has highest melting point.
and
STATEMENT-2 : Due to lowest surface area it will involve weakest van der Waal’s interaction.
Sol. Answer (2)
13. STATEMENT-1 : readily gives electrophilic addition reaction.
and
STATEMENT-2 : It is a non-aromatic compound.
Sol. Answer (2)
SECTION - E
Matrix-Match Type Questions
1. Match the given compounds in Column-I to their total possible halogenated product (number) in
Column-II
Column-I Column-II
(A) 2 methyl butane (p) 1
(B) Toluene (q) 3

(C) 2-methyl propane (r) 4
(D) 2, 2-dimethylpropane (s) 2

Sol. Answer A(r), B(r), C(s), D(p)
CH3
(1) CH3
CH3 CH3
(2)
(3) , CH3 — CH — CH3 , CH3 — C — CH3
(4) (1) (2)
CH3
(only 1)
2. Match the following

Column-I Column-II
Br2
(A) 1-butene  (p) Syn addition
KMnO 4
(B) cis-2-butene    (q) Anti addition
OH
RCO 3H
(C) trans-2-butene   (r) Meso form
Li / liq. NH3
(D) 2, 3-dimethyl-2-butene     (s) Racemic mixture
Sol. Answer A(q), B(p, r), C(q, r), D(q)
Br2, RCO3H/H2O/H+ & Li/liq. NH3 are antiaddition type reagents Baeyer’s reagent (KMnO4/OH–) is a syn
addition reagent.
3. Match the reaction given in Column-I to its name in Column-II

Column-I Column-II
CH3 CH3 CH3

| | |
(A) CH3 — C — CH — CH2   CH3 — C — CH — CH3 (p) Oxymercuration-demercuration
| |
CH3 OH
CH3 CH3
| |
(B) CH3 — C — CH — CH2   CH3 — C — CH — CH3 (q) Alkoxymercuration-demercuration
| | |
CH3 CH3 OH
CH3 CH3
(C) CH3 — C — CH — CH2  CH3 — C — CH2 — CH2OH (r) Acid catalysed hydration
CH3 CH3
CH3 CH3
| |
(D) CH3 — C — CH — CH2  CH3 — C — CH — CH3 (s) Hydroboration oxidation
| | |
CH3 CH3 OR
Sol. Answer A(r), B(p), C(s), D(q)

Oxymercuration demercuration follow Markownikov’s addition of H 2 O without forming Carbocation
Alkoxymercuration forms ethers without forming carbocation
Acidified hydrolysis follows carbocation mechanism hydroboration forms anti-Markownikoff product.

Column-I Column-II
(Compounds) (Effect exerted by substituent)
Cl
(A) (p) – I effect
CH3
O
(B) (q) Deactivating group
NO2
(C) (r) + R effect
OH
(D) (s) Activating group
Sol. Answer A(p, q, r), B(p, r, s), C(p, q), D(p, r, s)
In Cl, –I effect predomination over + R effect
–OCH3 is a group of +R and activating towards substitution electrophilic reaction
–NO2 is a group of –R effect and deactivating towards substitution electrophilic reaction
–OH is a group of +R effect and activating towards substitution electrophilic reaction

Column-I Column-II
CH3
(A) (p) Markovnikov's addition of HCl

CH3
CH3
(B) (q) Chiral centre is generated when
H hydrolysed with dil. H2SO4
CH–CH3
(C) (r) Can show gometrical isomerism
CH=CH–CH3
(D) (s) Degree of unsaturation is 2
(t) Chiral molecule
Sol. Answer A(q, r, s, t), B(p, r, s), C(p, q, r, t), D(r, s)
Markownikov’s addition is possible in unsymmetrical alkenes if there is no rearrangement. For optical

activity there should by chirality. Geometrical isomerism is due to hindered rotation.
6. Match the column
Column-I Column-II
(A) CH2 C CH CH2 (p) Can absorb at least 4 H2 molecules.

|
CH3
CH3
(B) (q) Decolourises bromine water
CH–CH3
(C) (r) 1, 4-addition of HCl is possible
(D) (s) Oxalic acid is formed after oxidative

ozonolysis
(t) Forms acetaldehyde as a product on

reductive ozonolysis
Sol. Answer A(q, r), B(p, s), C(p, q, r, t), D(p, q, r)
Compounds having 4 unsaturation factors can absorb four H2 molecules. Except benzene all given
compounds can decolourise bromine water.

Column-I Column-II
Hg /H 2 
(A) CH3  C  CH   (p) Electrophilic addition
CH3
|
HCl
(B) CH3  CH  
CH CH2   (q) Nucleophilic addition
Br /Fe
(C) 
2
 (r) Rearrangement takes place
CH3
| 
OH  aq
(D) CH3  C  CH2  Cl   (s) Optically inactive product
|
CH3
(t) Carbocation is formed

Sol. Answer A(q, s), B(p, r, t), C(s, t ), D(r, s, t)
In alkynes, nucleophilic addition takes place due to presence of Hg+2. In carbocations, rearrangements are
possible to gain more stability. Optical isomerism is observed due to presence of chirality.
SECTION - F
Integer Answer Type Questions
CH2
1. The unsaturation factor of is
CH2
Sol. Answer (6)
No. of H in CnH2n 2  no. of H in compound  no. of x

U.F. 
2
2. The total number of isomeric alkenes possible by C4H8 are ____.

Sol. Answer (4)
1-butene, isobutene & cis-trans -2-butene
3. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH
is [IIT-JEE-2011]
Sol. Answer (5)
Br Alc. KOH
+ +
(E + Z) (E + Z)
3-bromo-3-cyclopentylhexane
1 + 2 + 2
Total =5
Note : Dehydrobromination of alkyl bromides in the presence of alc. KOH follows E2 mechanism. Hence
no rearrangement in alkyl chain is possible
4. The number of hydroxyl group(s) in Q is [JEE(Advanced)-2015]
H 
H 
 P 
aqueous dilute KMnO4 (excess)
Q
heat 0 C
HO
H3C CH3
Sol. Answer (4)
Aqueous dilute OH
+
H H KMnO4 (excess)
Heat
HO OH
HO
(P) OH
SECTION - G
Multiple True-False Type Questions
1. STATEMENT-1 : Benzene can decolourise Baeyer's reagent.
STATEMENT-2 : CO2 can never be formed by reductive ozonolysis of hydrocarbons.
STATEMENT-3 : Acetylene forms musturd gas with sulphurmonochloride.
(1) TTT (2) F F T (3) F F F (4) T T F
Sol. Answer (3)
Benzene is resonance stabilised. CO2 is formed by ozonolysis of cumulative dienes. Ethene form mustard
gas.
2. STATEMENT-1 : Ethyne is more reactive than ethene towards hydrogenation.

STATEMENT-2 : H2 in presence of Lindlar catalyst is more reactive than H2 with Pd in hydrogenation reaction.
STATEMENT-3 : Dipole moment of o-xylene is greater than m-xylene.
(1) T F T (2) F T F (3) F F T (4) T T F
Sol. Answer (1)
Ethyne has more contact with catalytic surface. BaSO4 is poisonous in Lindlar’s catalyst.
SECTION - H
Aakash Challengers Questions
1. During pyrolysis of alkanes, C — C bonds break rather than C — H bonds. Why?
Sol. Bond energy of C — C bond is lower (by approximately 15 kcal) than C — H bonds
2. Propane is brominated in presence of uv light. All the isomeric product formed, if brought under Wurtz’s
synthesis, what products are expected?
Br
h Br +
Sol.  Br2 

(Minor) (Major)
Possible products are , &
3. Phenyl substituted hydrocarbon (A) molecular mass 120 on monobromination can give 3 isomeric products only.
Major product (B) on treatment with sodium metal gives (C). Find (A), (B) and (C).
Br
Br2
Sol. h
Major
Br Na
2
ether
4. Write all the products obtained by treatment of n-hexane with diazomethane.

h
Sol. CH2N   CH2  N2
Products formed
CH3
CH3(CH2)5 — CH3 |
CH3 — CH2 — CH2 — CH2 — CH — CH3
n-heptane
2-methyl hexane
CH3
|
CH3 — CH2 — CH2 — CH — CH2 — CH3
3-methyl hexane
5. Three compounds A, B and C all have molecular formula C5H8. All the compound rapidly decolourise Br2 in
CCl4, all three give a positive test with Baeyer’s reagent, and all the three are soluble in cold conc. H2SO4.
Compound A gives a precipitate when treated with ammoniacal AgNO3 solution, but compounds B and C do
not. Compounds A and B both yield pentane (C5H12) when they are treated with excess H2 in the presence
of Pt catalyst. Under these conditions, compound C absorbs only one mole of H2 and gives a product with
the formula C5H10
(a) Suggest a possible structure for A.
(b) Oxidative cleavage of B with hot basic KMnO4 gives, after acidification, acetic acid and CH3CH2COOH.
What is the structure of B?
(c) Oxidative cleavage of C with ozone gives OHCCH2CH2CH2CHO. What is the structure of C ?
Sol. (a) CH3 – CH2 – CH2 – C  CH
(b) CH3C  C – CH2CH3
(c)
6. An organic compound (A) of molecular formula C5H8 when treated with Na in liquid ammonia followed by reaction
with s-Propyl iodide yields (B) C8H14. (A) gives a ketone C5H10O (e) when treated with dil. H2SO4 and HgSO4.
(B) on oxidation with alkaline. KMnO4 gives two isomeric acids (D) and (E), C4H8O2. Give structures of
compounds (A) to (E) with proper reasoning.
Sol. (A) CH3 — CH2 — CH2C CH
CH3
(B) CH3 — CH2 — CH2 — C  C — CH
CH3
O
||
(C) CH3 — CH2 — CH2 — C— CH3
(D) CH3 CH2 CH2 COOH
CH 3
(E) CH — COOH
CH 3
7. A certain compound ‘A’ has a molecular formula C5H11Br. It reacts with Mg metal in anhydrous ether to form
compound ‘B’ which upon hydrolysis gives n-pentane. When compound A was reacted with Zn metal in dry
ether gave 4,5 dimethyl octane. What is A, B and draw their structures?
CH3
|
Sol. (A) CH — CH — CH — CH — Br
3 2 2
CH3
|
(B) CH3 — CH2 — CH2 — CH — Mg — Br
8. A hydrocarbon (A) adds one mole of hydrogen in the presence of platinum gives hexane. When (A) was
oxidised with KMnO4 it gave a single carboxylic acid, containing three carbon atoms. Give the structure and
name of (A).
Sol. (A) is 3-Hexene (CH3CH2 CH = CH CH2 CH3)
9. The melting points and boiling points for two C8H18 isomers are given below. Explain why CH3(CH2)6CH3 has
a lower melting point but higher boiling point.
mp (°C) bp (°C)
– 57 126
102 106
Sol. n-octane has higher boiling point due to stronger van der Waal’s interaction operating between various
molecules of n-octane due to its larger surface area than that of 2, 2, 3, 3-tetramethyl butane.
However due to more spherical geometry better stacking is present in 2, 2, 3, 3-tetramethyl butane which
results into higher melting point.
10. Explain why 2,2,5,5-tetramethyl-3-hexyne cannot be made using acetylide anions.
Sol.
2, 2, 5, 5-tetramethyl-3-hexyne
To prepare this compound we need acetylide ion and tertiary butyl halide. Tertiary butyl halide will give E2
reaction which results into formation of other compounds.
11. What would be the major product of the given reaction?

CH3
OH
C HCOOH
C H2O
CH3 CH3 O CH3 O CH3

C H
Sol. OH2 Taritomerisation
C
(i) B2H6 + THF

12. –
X
(ii) H2O2 / OH (Major)
Write the structure of (X) in the above reaction.

Sol. OH
(X)
13. Decalin is an example of fused bicyclic system where two six membered rings share common C—C bond.
There are two possible arrangements : trans and cis-decalin.
H H
H H
Decalin Trans-decalin Cis-decalin
(i) Draw cis and trans decalin using the chair form for these species.
(ii) Which isomer is more stable? Give explanation.
Sol. H
—
—
H
Cis-decalin
—
—
Trans-decalin
H
More stable
14. For which of the following species barrier of rotation along indicated bond is highest and lowest respectively?
H3C CH3 I I H3C CH3 Br Br

H2C—CH2 CH2—CH2 H2Si—SiH2 CH2—CH2
I II
III IV
Sol. The energy difference between the lowest and highest energy conformations is called the barrier of rotation.
Therefore (I) will have highest barrier of rotation while (III) will have lowest barrier of rotation.
15. Which of the following reactions is both stereoselective and regioselective?
(1) HBr (2) Br2

Peroxide, h CCl4
Cl2 BH3
(3) (4)
H2O THF
Sol. Answer (3, 4)

(3, 4) are both stereoselective and regioselective reaction.
OH H H
Cl B
H
Cl2 BH3
H2O THF
16. Which reagent will perform the following transformation? Write plausible mechanism to justify your answer.
MeO OMe
(1) KMnO4 followed by MeOH (2) CrO3 followed by MeOH

(3) DMSO, (COCl)2, MeOH (4) Tl(NO3)3, MeOH
Sol. Answer (4)

Due to inert pair effect Tl3+ trans forms into Tl+1 and hence Tl3+ involves rearrangement of alkene skeleton.
17. Which double bond in the given molecule is most reactive towards an electrophile?
A
B
D C
(1) A (2) B (3) C (4) D

Sol. Answer (4)
Attack of E+ on D double bond will result into the formation of most stable carbocation.
18. Which of the following reagents can be used to bring about the given transformations?
O O O O
?
MeO MeO
(1) H2/PtO2 (2) H—N=N—H (3) LiAlH4 (4) BH3/THF

Sol. Answer (2)
Diimide (N2H2) is a very mild selective reagent which does not reduce epoxide in the given condition.
19. 896 ml vapour of a hydrocarbon ‘A’ having carbon 87.80% and hydrogen 12.19% weighs 3.28 g at STP.
Hydrogenation of ‘A’ gives 2-methyl pentane. Also the hydration of hydrocarbon ‘A’ gives compound ‘B’.
Compound ‘B’ gives yellow precipitate with sodium hypoiodite. Find the structure of A and give the reactions
involved.
Sol. 896 ml vapours of CxHy (A) weighs 3.28 g
 Molecular weight of A = 83.1 g/mol
Empirical formula of A : C3H5
 Empirical formula mass = 36 + 5 = 41
83.1
 n 2
41
 Molecular formula is C6H10
(H)
C6H10
 +
H /H2O NaOI
Y CHI3 + (Z)
2+
Hg
 The compound is
20. Which of the following reaction will result into the formation of resolvable mixture?
(1) Treatment of but-1-ene with HBr in the presence of AIBN at 100°C. (AIBN = Azobisdiisobutyronitrite)
(2) Treatment of but-1-ene with HBr
(3) Treatment of N-bromosuccinimide with cis-pentene at 120°C
(4) Treatment of Br2 with trans-stilpene
Sol. Answer (2, 3)
NBS
AIBN
*
Br
cis-pentene Major
Chiral
Therefore racemic mixture
would be obtained
HBr
*
Br
Chiral
(Resolvable mixture)
21. What product would be obtained from the reaction of cyclopropane with Cl2 in the presence of FeCl3?
(1) 1, 2-dichloropropane (2) 1, 2-dichlorocyclopropane
(3) 1, 3-dichloropropane (4) 1, 1-dichloropropane
Sol. Answer (3)
–
Cl—Cl + FeCl3 Cl + [FeCl4]
Cl
Cl Cl
Cl
Cl
22. What products are formed when (R)-2-chloro pentane is brominated at the 3-position to form 3-bromo-2-chloro
pentane?
(1) Different amounts of (2R, 3R)-3-bromo-2-chloropentane and (2R, 3S)-3-bromo-2-chloropentane are formed
(2) Equal amount of (2R, 3R)-3-bromo-2-chloropentane and (2R, 3S)-3-bromo-2-chloropentane are formed
(3) Different amounts of (2R, 3R)-3-bromo-2-chloropentane and (2S, 3S)-3-bromo-2-chloropentane are formed
(4) Only (2R, 3R)-3-bromo-2-chloropentane is formed
Sol. Answer (2)
H H
Br2
Me Cl Me Cl
h or 
R-2-Chloropentane Intermediate which will

abstract Br from both sides
 equal mixture
23. Assuming that no rearrangement is taking place, then how many hydrocarbons are obtained from the reaction
of 2-chloropentane with isopropyl chloride in the presence of sodium. Do not include stereoisomers.
Sol. Answer (7)
+
Cl
2-chloropentane
+
+
Cl
Isopropylchloride +
+
+
24. Arrange the following hydrocarbons in the increasing order of enthalpy of combustion.
I II III IV
Sol. Answer (II < I < III < IV)

Due to the presence of highly strained bicyclic system in IV it is least stable and hence have highest enthalpy
of combustion.
25. Consider the following reactions
KOC(CH3)3
CHBr3 [X] [Y]
(CH3)3COH
CH2I2 + Zn [I] [II]
Correct statements regarding products [Y] and II is/are

(1) They are structural isomers (2) They are diastereomers
(3) They are enantiomers (4) They are identical
Sol. Answer (4)
(CH3)3COK CH2I2 + Zn
CHBr3


Cls Jeead-17-18 Xi Che Target-4 Set-2 Chapter-13

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Cls Jeead-17-18 Xi Che Target-4 Set-2 Chapter-13

Uploaded by

Copyright:

Available Formats

Chapter 13

2. Alkanes can be iodinated in the presence of

Sol. Answer (3)

4. Highest boiling point is expected for

5. (CH3)3CMgCl on reaction with D2O produces

6. Consider the folllowing reaction

(1) CH 3 CH CH CH2 (2) CH3 CH C CH3

7. In the given reaction

∵ 8 g Br2 reacts with 2.8 g alkene

9. Consider the following statements : a hydrocarbon of molecular formula C5H10 may be

The most suitable sequence of reagents to perform this conversion is

11. The compound having only primary hydrogen atoms is

12. Which equation does not represent an example of Friedel-Crafts reaction?

Sol. Answer (2)

13. In the reactions,

CH2 acid CH2 OH

CH 2 HOCl CH2OH Aq NaHCO3 CH2–OH

CH3 O CH3 CF3

> > >

17. HBr reacts with CH2 at room temperature to give

(1) CH3 CHO and CH3OH (2) BrCH2CHO and CH3 OH

(3) BrCH2 CH2 O CH3 (4) H3C CHBr OCH3

18. Colouration of Br2 / CCl4 will be discharged by

Cinnamic acid Benzoic acid

It is an unsaturated acid hence shows addition with bromine

19. CH2 CH CH CH2 

(1) (2) CH2 C C CH2 (3) CH 2 CH CH CH 2 (4)

Sol. Answer (3)

The ozonolysis product is

(3) H C CH3 (4) H C C CH3

21. Consider the following reaction

The reactive intermediate involved in this reaction is

(Radical anion) – a reactive intermediate

Sol. Answer (2)

(1) (2) (3) (4)

Sol. Answer (1)

25. The reaction

(1) (CH3)2C CH2 (2) CH3 — CH CH2

(3) CH3 — CH CH — CH3 (4) CH3 — CH2 — CH CH2

Sol. Answer (1)

CH3 CH3 CH3 CH3

28. The reaction of chlorine water with propene gives

(1) ClCH2 — CH(OH)CH3 (2) CH2(OH)CH(Cl)CH3

(3) ClCH2CH2CH2OH (4) ClCH(OH)CH2CH3

Sol. Answer (1)

(1) CH2 CH — CBr CH2 (2) CH3 — CHBr — C CH

(3) CH2 CH — CH CHBr (4) CH3 — CH2 — C C — Br

Sol. Answer (1)

30. Point out A in the given reaction sequence

(1) (2) (3) (4)

Sol. Answer (3)

the structure of the major product ‘X’ is [IIT-JEE-2007]

Sol. Answer (2)

Ring 1 is activated by NH group

32. The reagent(s) for the following conversion. [IIT-JEE-2007]

(1) Alcoholic KOH (2) Alcoholic KOH followed by NaNH2

(3) Aqueous KOH followed by NaNH2 (4) Zn/CH3OH

Sol. Answer (2)

(1) BrCH2CH2CH2CH2CH3 and CH3CH2C  CH (2) BrCH2CH2CH3 and CH3CH2CH2C  CH

(3) BrCH2CH2CH2CH2CH3 and CH3C  CH (4) BrCH2CH2CH2CH3 and CH3CH2C  CH

Sol. Answer (4)

34. The compounds P, Q and S

Sol. Answer (3)