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Match the reactants given in Column-I with the reagent given in Column-II of reagent in the preparation of
cyclobutane
Column-I
Column-II
COOH
(A)
COOH
(B)
COOH
(C)
PART - II : COMPREHENSION
Read the following passage carefully and answer the questions.
Comprehension-1
An alkene having molecular formula C6H12 gives a hydrocarbon X (C6H14)on catalytic hydrogenation.
Compound A gives two monochloro product Y and Z.
2.1
2.2
(C)
Hydrocarbon X is -
CH3
(A) H3C CH2 CH2 CH2 CH2 CH3
CH3
(C)
CRK
15
HYDROCARBONS
2.3
CH3
CH3
(B) H3C C CH CH3 , CH3 CH2 CH2 CH2 CH2 CH2 Cl
CH3 Cl
CH3 CH3
(C) H3C C C CH3 , CH3 CH2 CH2 CH2 CH2 Cl
Cl
H
CH3 CH3
Cl
CH3
Cl
Comprehension-2
The addition of hydrogen to an alkene is an exothermic
reaction & the enthalpy change is called the heat of
hydrogenation. More branched alkenes are more stable and
have less potential energy. The alkene having higher potential
energy releases more heat on hydrogenation. In the figure
the enthalpy changes of three isomeric alkenes has been
shown.
2.4
From the above statement & graph identify P if P, Q & R are the isomers of butene :
(A)
2.5
CRK
(D)
C H3
|
(A) CH3 CH CH CH2
C H3
|
(B) CH3 C CH CH3
C H3
|
(C) CH2 C CH2 CH3
16
HYDROCARBONS
Comprehension - 3
When alkyne passed into dilute sulphuric acid at 330 K in the presence of HgSO4 (catalyst), alkynes add one
molecule of H2O to form carbonyl compound.
H2SO 4 ,HgSO4
H C C H + H2O
CH3 CH = O.
H2SO 4 ,HgSO4
CH3 C CH + H2O
In fact, enols are formed in the hydration of alkynes. An alcohol contain OH group on a double bonded carbon is
called an enol. Enols can not be isolated because they are unstable and are rapidly converted into corresponding
aldehydes or ketones.
Based on above passage answers the given questions.
2.6
2.7
3-Methylbut-1-yne reacts with mercuric acetate in presece of water to form a product, which on reduction with
NaBH4 yield.
(A) 2-Methylbuten-2-ol
(B) 3-Methylbutanone
(C) 3-Methylbutan-2-ol
(D) 2-Methylbutan-2-ol
Comprehension - 4
The classical reagent for cleaving the carbon-carbon double bond is ozone. Ozonolysis (cleavage by ozone) is
carried out in two stage : first addition of ozone to the double bond to form an ozonide; and second, hydrolysis
of the ozonide to yield the cleavage product. Ozone gas is passed evaporation of the solvent leaves the ozonide
as a viscous oil. This unstable, explosive compound is not purified, but is treated directly with water generally in
the presence of a reducing agent.
Zn
H2O
The compounds containing the C=O group are aldehydes and ketones.
Based on above passage answers given questions.
2.8
2.9
2.10
CRK
(C) 2-methylbut-2-ene
(D) 4-methylpent-3-ene
17
HYDROCARBONS
Comprehension - 5
Consider the following reaction :
P (C9H16)
P on ozonolysis gives nona2,8dione.
2.11
2.12
What is P ?
(A) 2,3dimethylcyclohexene
(C) 2,3dimethylcyclohept1ene
(B) 1,3dimethylcycloheptene
(D) 1,2dimethylcyclohept1ene
P is formed by :
(A) Elimination only
(C) Substitution and ring expansion
Statement-1: In the bromination of propane and 2-Methyl propane. 2-Methyl propane gives more stable
transition state.
Statement-2: 3 CH bond is weaker than 2 C H bond.
3.2
Statement-1 : In the free radical reaction, reaction slow down for the peroid of time during which inhibitor exists
and after which the reaction proceed normally.
Statement-2 :Oxygen as inhibitor slow down the reaction for some times.
3.3
Statement-1 : The melting point of neopentane is higher than n-pentane but boiling point of neopentane is lower
than n-pentane
Statement- 2 : Melting point depends upon packing of molecules whereas boiling point depends upon surface
area. Neopentane fits into crystal lattice readily but has minimum surface area.
3.4
Statements-1 : CH3 CCCH3 is more reactive for electrophilic addition reaction than CH3CH = CH CH3
Statements-2 : Carbocation intermediate formed in alkene is more stable than the alkyne
3.5
3.6
Statement-1 : When double and triple bonds are in conjugation, addition takes place at triple bond.
Statement-2 : When double and triple bond are not in the conjugation, addition takes place at double bond
3.7
BrCl
alco KOH
CH3 CH = CH2 CH3CHCl CH2Br
Statement-1 : CH3 CHBrCH3
Statement-2 : In above reaction product formed, is based on the principle of E2 & electrophilic addition reaction
by markownikov's rule.
3.8
CRK
Statements-1 : Reaction of HCl with But-2-ene in the presence or absence of peroxide will give same products.
Statement-2 : Above reaction is regioselective reaction.
18
HYDROCARBONS
Cis alkenes are formed by the reduction of alkyne by use of lindlars catalyst.
4.2
NaOH
COONa
Electrolysis
4.3
Although acetylene is acidic in nature it does not react with NaOH / KOH
4.4
Although acetylene is acidic in nature it does not react with NaOH / KOH
4.5
4.6
4.7
The treatment of an alkene with cold dilute alkaline KMnO4 gives cis-diols.
4.8
1-Pentyne can be distinguished from 2-Pentyne with the help of ammonical AgNO3 solution.
4.9
The addition of H2 to 2-Butyne using H2 and Lindlar's catalyst gives trans-2, 2-dimethyl ethene.
4.10
A secondary alcohol on oxidation gives a carboxylic acid containg the same number of carbon atoms.
4.11
1, 2 and 3 alcohols when passed across heated cupper we get aldehyde, ketone and alkene respectively.
CRK
19
HYDROCARBONS
2.
[JEE-99, 2/80]
O
||
(A) CH3 CH2 C CH3
3.
4.
[JEE-2000, 1/35]
(D) AgNO3 in ammonia
[JEE-2000, 1/100]
H2
Lindlar catalyst
5.
(B) NH2NH2, OH
(C) H2/Ni
[JEE-2000, 1/100]
(D) NaBH4
Hydrogenation of the adjoining compound in the presence of poisoned palladium catalyst gives.
[JEE-2001, 1/35]
(A) an optically active compound
(C) a racemic mixture
7.
CRK
[JEE-2001, 1/35]
20
HYDROCARBONS
8.
Identify X, Y and Z in the following synthetic scheme and write their structures.
(i) NaNH
alkaline KMnO
H / Pd .BaSO
2
4
4
X 2
Y Z
CH3CH2C C H
( ii) CH CH Br
3
[JEE-2002, 5/60]
9.
Identify a reagent from the following list which can easily distinguish between 1-butyne and 2-butyne.
(A) bromine, CCl4
(B) H2, Lindlar catalyst
(C) dilute H2SO4, HgSO4
(D) ammonical Cu2Cl2 solution
[JEE-2002, 3/90]
10.
Identify the set of reagents/reaction conditions X and Y in the following set of transformations.
X
[JEE-2002, 3/90]
11.
Hg2 / H
Ph C C CH3 A, A is :
(A)
(B)
[JEE-2003, 3/84]
(C)
(D)
12.
[JEE-2004, 3/84]
13.
Amongst the following the reagent that would convert 2hexyne into trans2hexene is
[JEE-2004, 3/84]
(A) H2 .Pt / O2
14.
(D) NaBH4
15.
(D) 8
(B)
(C)
(B) Ph H
(C)
[JEE-2005, 3/60]
(D)
(A) Ph OH
CRK
(C) 6
(A)
16.
(B) 4
[JEE-2005, 3/60]
(D)
21
HYDROCARBONS
17.
Cl / h
Fractional
[JEE-2006, 5/184]
The number of possible isomers [N] and number of fractions [P] are
(A) (6, 6)
18.
(B) (6, 4)
(C) (4, 4)
Br
?
Br H
is/are
(A) alcoholic KOH
(C) aqueous KOH followed by NaNH2
19.
20.
(D) (3, 3)
(B) 2
(C) 3
(D) 4
(A)
(B)
(C)
(D)
O
P
(C6 H10 )
CRK
C
H3C
CH3
(ii) O3
(iii) Zn/H2O
22
HYDROCARBONS
21.
H3C
H3C
(C) H C C
H3C
22.
(D) H3C C C
H3C
C CH3
CH
H3C
OH
H3C
(A) H C C CH2CH3
H3C
H
H3C
OH
OH
OH
(C) H C CH2CHCH3
H3C
23.
24.
(A) a hemiacetal
(B) an acetal
(C) an ether
(D) an ester
25.
The maximum number of isomers (including stereoisomers) that are possible on monochlorination of the following
compound is :
[JEE 2011 160/4]
26.
The number of optically active products obtained from the complete ozonolysis of the given compound is
CH3
H3C
CH
CH
C
H
(A) 0
CRK
(B) 1
CH
H
CH
C CH
CH CH3
CH3
(C) 2
(D) 4
23
HYDROCARBONS
(2) Sn HCl
(3) Zn Hg
[AIEEE-2003]
(4) Pd / H2
2.
On mixing a certain alkane with chlorine and irradiating it with U. V. light, it forms only one monochloroalkane.
This alkane could be :
[AIEEE-2003]
(1) Propane
(2) Pentane
(3) Isopentane
(4) Neopentane
3.
Which one of the following is reduced with Zn/Hg and hydrochloric acid to give the corresponding hydrocarbon
[AIEEE-2004]
(1) Ethyl acetate
(2) Acetic acid
(3) Acetamide
(4) Butanone
4.
[AIEEE-2005]
5.
[AIEEE-2003]
(1) Zn HCl
6.
(2) Sn HCl
(3) Zn Hg
(4) Pd / H2
(2) ClCH2COOH
[AIEEE-2003]
(3) CH3COCl
(4) ClCH2CHO
7.
Reaction of one molecule of HBr with one molecule of 1, 3-butadiene at 40C gives predominantly :
(1) 1-Bromo-2-butene under kinetically controlled conditions
[AIEEE-2005]
(2) 3-Bromobutene under thermodynamically controlled conditions
(3) 1-Bromo-2-butene under thermodynamically controlled conditions
(4) 3-Bromobutene under kinetically controlled conditions
8.
9.
[AIEEE-2007, 3/120]
10.
The hydrocarbon which can react with sodium in liquid ammonia is:
[AIEEE-2008, 3/105]
(1) CH3CH2 CCH
(2) CH3CH = CHCH3
(3) CH3CH2CCCH2CH3
(4) CH3CH2CH2CCCH2CH2CH3
11.
One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular mass of
44 u. The alkene is :
[AIEEE-2010, 4/144]
(1) propane
(2) 1-butene
(3) 2-butene
(4) ethene
12.
The hybridisation of orbitals of N atom in NO3, NO2+ and NH4+ are respectively :
(1) sp, sp3, sp2
13.
How many chiral compounds are possible on monochlorination of 2 - methyl butane ?[AIEEE-2012, 4/120]
(1) 8
CRK
[AIEEE-2011, 4/120]
(2) 2
(3) 4
(4) 6
24
HYDROCARBONS
14.
Which branched chain isomer of the hydrocarbon with molecular mass 72 u gives only one isomer of mono
substituted alkyl halide ?
[AIEEE-2012, 4/120]
(1) Tertiary butyl chloride
(2) Neopentate
(3) Isohexane
(4) Neohexane
15.
16.
(3) Pd/BaSO4
(4) LiAlH4
In the given transformation, which of the following is the most appropriate reagent ? [AIEEE-2012, 4/120]
CRK
(2) Li/NH3
[AIEEE-2012, 4/120]
(2) Zn Hg/HCl
(4) NaBH4
25
HYDROCARBONS
ANSWER KEY
EXERCISE - 1
1.1
(D)
1.2
(A)
1.3
(D)
1.4
(B)
1.5
(B)
1.6
(A)
1.7
(D)
1.8
(A)
1.9
(B)
1.10
(D)
1.11
(B)
1.12
(D)
1.13
(A)
1.14
(B)
1.15
(C)
2.1
(D)
2.2
(A)
2.3
(D)
2.4
(C)
2.5
(B)
2.6
(D)
2.7
(A)
2.8
(C)
2.9
(B)
2.10*
(A,B)
3.1
(A)
3.2
(A)
3.3
(A)
3.4*
(B,C)
3.5
(C)
4.1
(B)
4.2
(D)
4.3
(A)
4.4
(B)
4.5
(B)
4.6
(B)
4.7
(B)
(C)
4.10
(C)
4.11
(B)
4.12
(B)
4.13
(B)
4.14
(D)
4.15
(B)
4.16
(A)
4.17
(B)
4.18
(A)
4.19
(A,B,C) 4.20
(C)
4.21
(A)
4.22
(C)
4.23
(D)
4.24
(A)
(C)
4.27
(C)
4.28
(A)
4.29
(A)
4.30
(B)
4.31*
(A,B,C) 4.32
(B)
4.33
(A)
4.34
(A)
4.35
(B)
4.36
(D)
4.37
(C)
4.38
(D)
(B)
4.40
(B)
4.41
(C)
4.42
(A)
4.43
(A)
4.44
(A)
4.39
EXERCISE - 2
1.1
(i)
trans
1.2
(i) H2/Pd-BaSO4-CaCO3
(ii) In this conversion CO converts into CH2 which can be achieved by any one of the following reagents :
(a) NH2NH2/KOH/
1.3
ZnHg / HCl
CH3CHO
CH3CH3
(A)
1.4
(B)
CaO
CH3CH2CH2 COONa + NaOH CH3CH2CH3 + Na2CO3
630K
CaO
CH CH CH + Na CO
+ NaOH 630
3
2
3
2
3
K
CRK
26
HYDROCARBONS
1.5
Ether
(i) CH3 CH2 Cl + 2Li
CH3CH2Li + LiCl
1.6
X is
1.7
1.8
(i)
2.1
Chlorination of methane is a free radical reaction which occurs by the following mechanism
(ii)
X=
;Y=
Homolytic Fission
Initiation
Propagation
+ HCl
CH3 Cl +
Termination
CH3 CH3
CH3 Cl
Cl Cl
2.2
(4)
(d and )
3.1
A is more stable.
4.1
CH3CH CHCH3
But 2 ene
CRK
(d and )
3.2
C2H2
27
HYDROCARBONS
4.2
4.3
4.5
Since (I) is more stable so it contributes more to the resonance hybrid and reacts faster with the bromide ion.
4.6
4.7
(a) (CH3)2C=CHCH(CH3)2
4.8
4.9
(a)
(b) CH3CH2CH=CHCH2CH3
and enantiomer
(b)
(c)
(d) Na / ether
and enantiomer
(c)
and enantiomer
EXERCISE - 3
1.1
2.1
(C)
2.2
(C)
2.3
(A)
2.4
(B)
2.5
(B)
2.8
(D)
2.9
(A)
2.10
(A)
2.11
(D)
2.12
(B)
3.1
(A)
3.2
(B)
3.3
(A)
3.4
(D)
3.5
3.7
(C)
4.1
4.2
4.3
4.4
4.5
4.8
4.9
4.10
CRK
2.6
(B)
2.7
(C)
(C)
3.6
(B)
3.7
(A)
4.6
4.7
28
HYDROCARBONS
EXERCISE - 4
PART - I : IIT-JEE PROBLEMS (PREVIOUS YEARS)
1.
(A)
2.
In presence of Lindlars catalyst (Pd & CaCO3 in quinoline) partial hydrogenation takes place and gives cisisomer .
H2
Lindlar 's catalyst
3.
(D)
4.
In presence of lindlars catalyst (Pd and CaCO3) in quinoline) partial hydrogenation takes place and give cisisomer.
H2
Lindlar catalyst
5.
(B)
6.
(B)
7.
(B)
8.
CH CH C C Na
CH3 CH2 C CH
( NH3 )
3
2
( i ) NaNH
CH3 CH2 C
| |
H H
y
C . CH2 CH3
( Compound ' X )
OH OH
| |
CH3 CH2 C C CH2 CH3
| |
H H
(Compound ' Z' )
9.
(D)
10.
(A)
11.
(A)
12.
(A)
13.
(C)
14.
(B)
15.
(A)
16.
(B)
17.
(B)
18.
(B)
19.
(A)
20.
(A)
21.
(D)
22.
(B)
23.
24.
(B)
25.
26.
(A)
(4)
2.
(4)
3.
(4)
4.
(4)
5.
(4)
6.
(1)
7.
(3)
8.
(3)
9.
(1)
10.
(1)
11.
(3)
12.
(4)
13.
(3)
14.
(2)
15.
(2)
16.
(1)
CRK
29