ALLEN® Chemistry : Hydrocarbons

Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ALKANES
7. O can not be converted to by :
1. The order of reactivity of alkyl halides in Wurtz
(1) Red P + HI
reaction is
(2) Wolf Kishner reduction
(1) R–I > R–Br > R–Cl (2) R–I < R–Br < R–Cl (3) Clemmensen reaction
(3) R–Br > R–I < R–Cl (4) R–I > R–Cl > R–Br (4) LiAlH4
HC0001 HC0010
8. Which of the following reactions does not involve
2. Kolbe's electrolysis of a mixture of pot. a C–C bond formation
Propanoate and pot. 3-Methylbutanoate gives (1) Hydrolysis of a Grignard reagent
(1) Butane and isobutane (2) Combination of two alkyl free radicals
(2) Butane and 2,5–dimethylhexane (3) Corey-House synthesis of alkanes
(3) Butane, 2,5-dimethylhexane and isohexane (4) RNa + R–Br  R–R + NaBr
(4) Butane and isohexane HC0012
HC0002 9. Which of the following reactions of methane is
incomplete combustion :-
Cu /523K /100atm.
3. The Corey-House alkane synthesis is carried out EN (1) 2CH4 + O2   2CH3OH
Mo 2O 3
by treating an alkyl halide with (2) CH4 + O2   HCHO + H2O
(1) Lithium metal (3) CH4 + O2  C(s) + 2H2O()
(2) Copper metal (4) CH4 + 2O2 CO2(g) + 2H2O()
(3) Lithium metal followed by reaction with HC0016
cuprous iodide and then treating the product 10. Which is correct about Wurtz reaction ?
with an alkyl halide (a) It can proceed through free radical
LL
(4) Cuprous iodide followed by reaction with alkyl mechanism
halide (b) Alkanes having even no. of C-atom can be
HC0003 prepared
(c) Sodium in Ammonia is used
4. Which of the following compound is not suitable
(d) Sodium in dry ether is used
A

to obtain from wurtz reaction ?

(1) c, d (2) a, b, d
(1) ethane (2) butane (3) b,c (4) a, b, c, d
(3) isobutane (4) hexane HC0072
HC0005 Zn,
11. C2H5–Cl (A)
H2
5. When ethyl chloride and n-propyl chloride
Na H2/Pt
undergoes wurtz reaction which is not obtained (B) (C) or (D)
Dry ether
(1) n-butane (2) n-pentane
(3) n-hexane (4) isobutane The incorrect statement is :
HC0006 (1) (A) is C2H6 (2) (C) can be 1-butene
(3) (A) and (B) are alkane (4) (D) is ethene
CH3 HC0073
6. CH3–CH–MgCl + CH3–C–OH  'Q'; 12. Arrange the following in their boiling points.
CH3 CH3 (i) n-butane (ii) iso-butane
(iii) n-pentane (iv) iso-pentane
What is 'Q' ?
(v) neopentane
(1) isobutane (2) isopropane
(1) iii > i > ii > iv > v (2) v > iv > ii > i > iii
(3) tert. butyl chloride (4) propane (3) iii > iv > v > i > ii (4) ii > i > v > iv > iii
HC0009 HC0074
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O 19. Which of the following is not electrophilic
13. For CH3–C–ONa (A) alkane
Electrolysis addition reaction ?

Which is incorrect ? (1) Addition of H+/H2O on alkene

(1) A is ethane
(2) (A) is formed at anode (2) Addition of dihydrogen on alkenes
(3) CO2 evolves at cathode (3) Addition of halogen on alkenes
(4) pH near cathode increases during the process
(4) Addition of hydrogen halides on alkenes
HC0075
HC0077
ALKENE
Br
14. Ozonolysis of 3–Methyl–1–butene gives a
20. CH3–CH=CH2 
HBr
 CH3–CH–CH3
mixture of
(1) Propanal and ethanal (A)
+
(2) Propanone and ethanal CH3–CH2–CH2–Br
(3) 2–Methylpropanal and methanal (B)
(4) Butanone and methanal
HC0017 (a) The product A is major
15. Oxidation of isobutylene with acidic potassium (b) Formation of A follows markovnikov rule
permanganate gives
(1) Acetone + CO2 (2) Acetic acid EN (c) Carbocation formed in A is less stable than
(3) Acetic acid + CO2 (4) Acetic acid + acetone that formed in B
HC0019
(d) Formation of B follows markovnikov rule
 A B+C
(i) O
16. CH3CH2CH2Br 
alc. KOH

3
(ii) Zn, H2O
The correct statements are :
In the above reaction A, B and C are given by
the set (1) c, d (2) a, b, c, d
(1) Propylene, acetone, formaldehyde
(3) a, b (4) a, d
LL
(2) Propene, ethanal, methanal
(3) Propyne, acetaldehyde, formaldehyde HC0078
(4) Propylene, propionaldehyde, formaldehyde
HC0021 21. For the reaction

17. Which of the following alkenes on ozonolysis CH2=CH2 

Br
(A) 
2alc. KOH
 (B)  (C)
NaNH 2

CCl4
give a mixture of ketones only?
A

(a) CH3–CH=CH–CH3 The product (C) is :

(b) CH3–CH–CH=CH2 (1) CH2=CH2 (2) CH2=CH
CH3 Br
CH3
(c) C (3) H–CC–H (4) CH2–CH3
CH3 Br
CH3
(d) (CH3)2C=C HC0079
CH3
(1) a and b (2) b and c 22. An alkene A on ozonolysis gives a mixture of
(3) b and d (4) c and d ethanal and pentan-3-one. The IUPAC name of
HC0025
A is.
18. Which reaction will not happen at room
temperature: (1) 3-ethyl-3-pentene
(1) CH2=CH2 
H2 /Pt

 CH3–CH3 (2) 3-ethylidene pentane
(2) CH2=CH2 
H2 /Pd
 CH3–CH3
(3) 3-ethyl pent-2-ene
(3) CH2=CH2 
H2 /Ni
 CH3–CH3
(4) CHCH 
H2 /Pt

 CH3–CH3 (4) 1,1-diethyl prop-1-ene
HC0076 HC0080

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23. For the reaction :
28. 
Liq.NH3 product will be :
Na
CH3
CH3–CH–CH=CH2 
HBr
(A) (major) CH2 CH3
HO 2 2

CH3 HBr (1) C=C

(B) (major) H H
The incorrect statement is : CH2 H
(2) C=C
(1) A and B are chain isomers H CH3
(2) A and B are position isomers
H
(3) A is 1-bromo-3-methyl butane
(4) B is 2-bromo-2-methyl butane (3)
H CH3
HC0081
CH3
24. For the reaction C=C
(4) H
H3C H
O3
C=CH–CH3  (A) + (B) HC0031
Zn/H2O
H3C
Products
29. To distinguish between propene and propyne,
(1) One of the product only show positive tollens
the reagent would be -
test
(1) Bromine
(2) Both product shows positive tollen's test EN (2) Alkaline KMnO4
(3) Both product shows positive haloform test (3) Ammonical silver nitrate
(4) Both 1 & 3 are correct (4) Ozone
HC0082 HC0032
30. The most suitable reagent to differentiate ethyne
ALKYNES
and ethene is :
25. Which of the following compound will not give a (1) Br2 in CCl4 (2) NaHCO3
LL

(3) NaOH (4) NaNH2

precipitate with Tollen's reagent
HC0083
(1) ethyne (2) 1-butyne 31. For the reaction :
(3) 3-methyl-1-butyne (4) 1-pentene HBr
CH3–CCH (A)
HC0028
A

2+ +
Hg /H
(B)
B   CH3–CCH     A,
BH3 /THF HgSO 4 / H 2 SO 4
26. 333 K
H O / OH
2 2
Consider statements :-
A and B are Br
(a) Product A is CH3–CH2–CH
(1) CH3CH2CHO, CH3COCH3
(2) CH3COCH3,CH3 CH2CHO Br
Br
(3) CH3COCH3 both
(b) Product A is CH3–C–CH3
(4) CH3COCH3 , CH3 CH2 CH2 OH
HC0029 Br
(c) Product B is CH3–CH2–CH=O
27. MeCH2CCH 
NH /NaNH2
 A  B,
3 Et Br
(d) Product B is CH3–C–CH3
A and B are
(1) MeCH2CCNa, MeCH2CC–Et O

(2) MeCH2CH=CH2, MeCH2–CHEt–CH3 The correct statements are :

(1) b, d (2) a, c
(3) MeCH2CH=CHNH2,MeCH2CH=CH–NHBr
(3) only b (4) only a
(4) MeCH2CC–NH2, MeCC–NH–Br HC0084
HC0030

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AROMATIC HYDROCARBONS 34. For the reaction :

CH=CH2 
CH CH –CH –Cl
3 2
(A)
2

AlCl3
Br2 KMnO Correct statement is :-
32. A   
4
 B; A and B
(1) A is n-propyl benzene
respectively are (2) It is a friedel craft alkylation
(1) o-bromo styrene, benzoic acid
(3) A is iso propyl benzene
(2) p-bromostyrene, benzaldehyde
(3) m-bromostyrene, benzaldehyde (4) Both 2 & 3
(4) Styrene dibromide, benzoic acid AH0085
HC0035 35. For the reaction
6Cl2
33. The ozonolysis product of 1, 2-dimethyl benzene (A)
AlCl3(excess)
is/are :- Cl2(excess)
(1) Only CH3–C–C–CH3 hv 500 K
(B)

O O (1) A is not aromatic

(2) CH3–C–C–H + CH3–C–C–CH3 (2) B is aromatic
(3) A is aromatic
O O OO
(4) B is hexachlorobenzene
(3) H–C–C–H + CH3–C–C–CH3
AH0086
O O O O
(4) CH3C–CCH3 + HC–CH + CH3C–C–H

O O O O O O
EN
HC0036
LL
A

EXERCISE-I (Conceptual Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 1 3 3 3 4 4 4 1 3 2 4 3 3 3 1
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 2 4 3 2 3 3 3 1 4 4 2 1 2 3 4
Que. 31 32 33 34 35
Ans. 1 4 4 4 3

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Pre-Medical

EXERCISE-II (Previous Year Questions) AIPMT/NEET

AIPMT 2007 6. The oxidation of benzene by V2O5 in the
presence of air produces :
1. Reduction of aldehydes and ketones into
(1) benzoic acid (2) benzaldehyde
hydrocarbons using zinc amalgam and conc. HCl (3) benzoic anhydride (4) maleic anhydride
is called HC0046
(1) Cope reduction
(2) Dow reduction NEET(UG) 2018
(3) Wolf-kishner reduction
7. Hydrocarbon (A) reacts with bromine by
(4) Clemmensen reduction
substitution to form an alkyl bromide which by
AH0039
Wurtz reaction is converted to gaseous
2. Which of the compounds with molecular formula hydrocarbon containing less than four carbon
C5H10 yields acetone on ozonolysis atoms. (A) is
(1) 3-Methyl-1-butene (2) Cyclopentene (1) CHCH (2) CH2=CH2
(3) 2-Methyl-1-butene (4) 2-Methyl-2-butene (3) CH3–CH3 (4) CH4
HC0040 HC0049
8. The compound C7H8 undergoes the following
AIPMT 2010
reactions :
3Cl /  Br /Fe Zn/HCl
3. Liquid hydrocarbons can be converted to a C7H8 
2  A 
2  B 
C
mixture of gasesous hydrocarbons by :-
The product 'C' is
(1) Hydrolysis EN (1) m–bromotoluene
(2) Oxidation
(2) o–bromotoluene
(3) Cracking
(3) 3–bromo–2,4,6–trichlorotoluene
(4) Distillation under reduced pressure
(4) p–bromotoluene
HC0041
AH0050
AIPMT 2015 NEET(UG) 2019
4. A single compound of the structure :- 9. The most suitable reagent for the following
CH3 CH3 conversion is :-
LL

H3C CH3
OHC C C H3C–CC–CH3 
C H C O H H
H2 H2 cis-2-butene
is obtainable from ozonolysis of which of the (1) Na/liquid NH3 (2) H2, Pd/C, quinoline
following cyclic compounds ? (3) Zn/HCl (4) Hg2+/H+, H2O
A

H3C CH3 HC0087

H3C
(1) (2) 10. An alkene "A" on reaction with O3 and Zn–H2O
H3C gives propanone and ethanal in equimolar ratio.
Addition of HCl to alkene "A" gives "B" as the
CH3 H3C major product. The structure of product "B" is :-
(3) (4) CH3 CH3
CH3
(1) Cl–CH2–CH2–CH
HC0044
CH3
Re-AIPMT 2015 CH2Cl
5. 2,3–Dimethyl–2–butene can be prepared by (2) H3C–CH2–CH–CH3
heating which of the following compounds with a
CH3
strong acid ?
(1) (CH3)2C=CH–CH2–CH3 (3) H3C–CH2–C–CH3
(2) (CH3)2CH–CH2–CH=CH2 Cl
(3) (CH3)2CH–CH–CH=CH2 CH3
CH3 (4) H3C–CH–CH
(4) (CH3)3C–CH=CH2 Cl CH3
HC0045 HC0088
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11. Among the following, the reaction that proceeds CH2Cl CHCl2
through an electrophilic substitution is :

(3) (4)
(1) N2Cl 
Cu Cl 2 2
Cl + N2
AH0111
(2) + Cl2 
AlCl 3
Cl + HCl 16. An alkene on ozonolysis gives methanal as one
Cl Cl of the product. Its structure is :
CH2CH2CH3 CH=CH–CH3
(3) + Cl2 
UV light
Cl Cl
(1) (2)
Cl Cl
(4) CH2OH + HCl 
heat CH2Cl + H2O CH2–CH2–CH3 CH2–CH=CH2
AH0089
(3) (4)
NEET(UG) 2019 (ODISHA)
HC0112
12. The alkane that gives only one mono-chloro
product on chlorination with Cl2 in presence of
diffused sunlight is :- NEET(UG) 2020 (COVID-19)
(1) 2,2-dimethylbutane (2) neopentane CH3CH2CH = CH2 
17. B2H6
H O ,OH–
Z
(3) n-pentane (4) Isopentane 2 2

13. In the following reaction,

H 3 C  C  CH 
red hot
iron tube
873 K
 A,
HC0090
EN What is Z ?
(1) CH3CH2CH2CH2OH
(2) CH3CH2CHCH3
the number of sigma() bonds present in the OH
product A is :- (3) CH3CH2CH2CHO
(1) 21 (2) 9 (3) 24 (4) 18
AH0091 (4) CH3CH2CH2CH3
LL
HC0113
NEET(UG) 2020 NEET(UG) 2021
14. Which of the following alkane cannot be made in 18. The major product formed in
good yield by Wurtz reaction ? dehydrohalogenation reaction of 2-Bromo
(1) n-Butane (2) n-Hexane pentane is Pent-2-ene. This product formation is
(3) 2,3-Dimethylbutane (4) n-Heptane based on ?
A

HC0110 (1) Saytzeff's Rule (2) Hund's Rule

15. Identify compound X in the following sequence (3) Hoffmann Rule (4) Huckel's Rule
of reactions : HC0114
CH3 CHO NaOH, ?
19. CH3CH2COO–Na+ 
Heat
CH3CH3

Cl /hv
2
X 
HO 2 +Na2CO3.
373K
Consider the above reaction and identify the
CCl3 Cl missing reagent/chemical.
(1) B2H6 (2) Red Phosphorus
(1) (2) (3) CaO (4) DIBAL-H
HC0115

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 4 4 3 4 4 4 4 1 2 3 2 2 1 4 4
Que. 16 17 18 19
Ans. 4 1 1 3

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EXERCISE-III (Analytical Questions) Master Your Understanding

4. For the reaction given :-
1. 
Br
2
A 
alc. KOH
B; COOH
NaOH
What is the structure of B CaO, 
(A)
Br NaOH Electrolysis
(1) (2) (B) (C)
Which is incorrect ?
Br
(3) (4) (1) A is
HD0057
(2) C is
2. Which of the following is maximum reactive
towards NBS
(1) PhCH3 (3) C is
(2) Ph CH2–CH3
COONa
(3) PhCH2–CH=CH2
(4) Ph–CH–CH=CH2 (4) B is

CH3 HC0093
HC0058 40% H2SO4 X (y)
5. CH3–CC–H [Intermediate] Isomerism
Z
3. Which of the following is not carcinogenic ? 1% HgSO4

(1) (2)
EN Identify X, Y and Z
X
(1) Prop-1-en-2-ol
Y
Metamerism Acetone
Z

(2) Prop-1-en-1-ol Tautomerism Propionaldehyde

(3) Prop-2-en-2-ol Geometrical Acetone
isomerism
(4) Prop-1-en-2-ol Tautomerism Acetone
(3) (4)
HC0094
LL

HC0092
A

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5
Ans. 4 4 4 3 4

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