Hydrocarbon 1

HYDROCARBON
REACTION CHART FOR ALKANES

GMP GR
H 2 , Ni
(1) R–C CH X 2 , h or UV light or 400 C
200 300 C (1) RX
or Sabatier
R–CH=CH2 senderens rxn O
(2) Nitration
R–N
Zn Cu HCl or O
(2) R–X Red P / HI or LiAlH 4

HOH or ROH (3) Sulphonation H 2S2O 7

Alkyl Sulphonic acid
(3) R–Mg–X or NH 3 or RNH 2

Na/ dry ether

SO 2Cl2 Reed reaction
(4) RX Wurtz reaction
(4) RSO2Cl
h

Zn R–H
(5) RX Frankland's reaction or AlCl3 / HCl
R–R (5) Isomerisation
Branched alkanes
R C Cl or ROH Red P / HI or
(6) ||
O
CnH 2n+2
Pyrolysis
(6) 500 700 C
Alkenes + CH4 or C2H6
or
R C R or RCHO
(Cr) or (Mo) or Al2O 3
|| (7) Aromatic compound
500 C
O
Zn Hg / Conc. HCl
(7) R C R CH 2 N 2
|| Clemension reduction (8) step up rx n Higher alkane
O
H 2 N NH 2 O2
(8) R C O Wolf Kishner reduction
(9) CO2 + H2O
| Combustion
R
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

or
(RCH2CH2)3B H 2O

NaOH CaO
(9) RCOONa
(10) RCOONa Kolbe's electrolytic synthesis

(11) Al4C3 H 2O

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2 JEE-Chemistry
REACTION CHART FOR ALKENES
GMP GR
H 2 , Ni
(1) R–CH2–CH2–OH conc. H 2SO 4 (1) R–CH2–CH3
/ H 2O 200 300 C

alc. KOH X2
(2) R–CH2–CH2–X (2) R–CHX–CH2X
HX
HX
Zn dust / (3) R–CHX–CH3
(3) R–CH2–CH for higher alkene HBr , Peroxide
X2 (4) R–CH2–CH2Br
HOCl
R CH CH 2 Zn dust (5) R–CH(OH)–CH2Cl
(4) | | dil. H 2SO 4
X X (6) R–CH2(OH)–CH3
H2O
H 2 / Pd CH 2 N 2
(5) R–C CH (7)
BaSO4 / CaCO3

RCH COOK (8) BH 3 (RCH2CH2)3B

(6) | Kolbe's electrolytic synthesis
RCH COOK
CO H 2
R CH CH 3 R CH CH 2
2
(9) | + |
HCo ( CO ) 4 CHO
(7) (C2H5)4N+OH CHO
O2
Pyrolysis (10) CO2 + H2O
(8) R–CO–CH2–CH2–R
(i )OsO 4 R CH CH 2
O (11) (ii) NaHSO3 / H 2 O | |
(9) R–H Pyrolysis OH OH
(i )Mg
(10) CH2=CHCl (ii) Me I Baeyer ' s reagent R CH CH 2
(12) 1%alkalineKMnO4 | |
CH 2 PPh3
(11) R–CH=O wittig reaction
OH OH

(13) strong oxidant R C OH + CO + H O

|| 2 2

O
Per acid
(14) Pr iles chalev 's reaction

1 / 2 O2
(15)
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Ag 300 C

O 3 / Zn,H 2O
(16) ozonolysis
+
O2
(17) 200 C high P
Polyalkene
Cl2
(18) 500 C
Substitution product

Al2 (SO 4 )3
(19) 200 300 C
Isomerisation
acetic anhydride
(20) R–CH=CH–COCH3
Methyl alkenyl ketone

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 Hydrocarbon 3
REACTION CHART FOR ALKYNES
GMP GR
alc. KOH , NaNH 2 H2
(1) CH2Br–CH2Br (1) C2H4, C2H6
Ni
(2) CH3–CHBr2 alc. KOH , NaNH 2 X2
(2) C2H2X4
Ag powder HBr
(3) CHCl3 (3) CH2BrCH2Br
Peroxide
C 2 H2 HBr
(4) CHBr2–CHBr2 Zn dust (4) No peroxide CH3–CHBr2
HOCl
(5) Cl2CH–COOH
CHBr HCN , Ba ( CN ) 2
(5) || Zn (6) CH2=CHCN
CHBr CH 3COOH, Hg 2
(7) CH3CH(OCOCH3)2
(6) CH2=CH–Cl alc. KOH , NaNH 2
Hg 2 , 80 C , dil. H 2SO 4
(8) CH3CHO
HC COONa ( Kucherov 's reaction )
Kolbe's electrolytic synthesis
(7) || Dil.H2SO4 / HgSO4
HC COONa (9) CH3CHO
Kucherov ' s reaction
H 2O
(8) CaC2 CO HOH
(10) CH2=CH–COOH
electric arc,1200 C Ni( CO ) 4
(9) 2C + H2 Berthelot 's process
CO EtOH
(11) CH2=CH–COOEt
(10) CH3–C CH (i ) Na (ii) R X Ni ,160 C
CH3–C CR
NaNH 2
(i ) CH 3MgI (ii ) R X (12) NaC CNa
(11) CH3–C CH CH3–C CR
AgNO3 NH 4OH
(13) AgC CAg white ppt.
( Tollen 's Re agent )
H2O
(12) Mg2C3 CH3 – C CH Cu 2Cl 2 NH 4OH
(14) CuC CCu red ppt.
Combustion O2
(15) CO2 + H2O

Baeyer 's Reagent

CHO
(16) HCOOH
CHO

O3 H 2O
(17) Ozonolysis 2 HCOOH
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Tri m erisation
(18) (Red hot iron tube ) benzene
Tetramerisation
(19) C8H8or 1,3,5,7-cyclo octa tetraene
[ Ni (CN)2 ]

Dimerisation
(20) [Cu( NH 3 )2 ] or Cu 2 Cl 2 .NH 4Cl butenyne

s
(21)

CH 3OH CH(OCH3)2
(22) methylal
( BF3 HgO ) CH3

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4 JEE-Chemistry
EXERCISE # O-1
1. During the preparation of ethane by Kolbe’s electrolytic method using inert electrodes the pH of the
electrolyte –
(A) Increases progressively as the reaction proceeds
(B) Decreases progressively as the reaction proceeds
(C) Remains constant throughout the reaction
(D) May decrease of the the concentration of the electrolyte is not very high
HC0001
2. BrCH2–CH2–CH2Br reacts with Na in the presence of ether at 100 °C to produce –

(A) BrCH2–CH=CH2 (B) CH2=C=CH2 (C) (D) All of these

HC0002
3. How many products will be formed excluding stereo when cis-1,3,5-trimethyl cyclohexene reacts
with NBS?
(A) 3 (B) 4 (C) 5 (D) 6
HC0003
4. How many dibromo derivatives are formed when bromine is added to 3-Methyl Cyclohexene in
1,2-dichloroethane.
(A) 2 (B) 3 (C) 4 (D) 6
HC0004

Br2 NaI
5. P(Alkene) Q (Alkene)
CCl 4 Acetone

Alkene (P) & (Q) respectively are

(A) Both (B) ,

H
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Ph CH3
(C) Both (D) Both
C
Ph CH2

HC0005
6. Anti–Markownikoff’s addition of HBr is not observed in –
(A) Propene (B) But–2–ene (C) But–1–ene (D) Pent–2–ene
HC0006

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 Hydrocarbon 5

alcoholic KOH
7. Product ; Product is:

(A) (B) (C) (D)

HC0007
8. Which is expected to react most readily with bromine –
(A) CH3CH2CH3 (B) CH2=CH2 (C) CH CH (D) CH3–CH=CH2
HC0008
9. For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of
reactivity as measured by reaction rates:
(I) ClCH=CH2 (II) (CH3)2.C=CH2 (III) OHC.CH=CH2 (IV) (NC)2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C) III > II > IV > I (D) II > I > III > IV
HC0009

x
10. CH3–CH=CH–CH3 Product is Y (non–resolvable) then X can be –
cis
(A) Br2 water (B) HCO3H / H3O+
(C) Cold alkaline KMnO4 (D) all of the above
HC0010
11. The reaction of cyclooctyne with HgSO4 in the presence of a H2SO4 gives

(A) (B) (C) (D)

HC0011
H 2SO 4 NBS
12. P (Major) Q (Major)
The structure of Q is
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(A) (B) (C) (D)

HC0012
13. Acetylene may be prepared using Kolbe’s electrolytic method employing –
(A) Pot. acetate (B) Pot. succinate (C) Pot. fumarate (D) None of these
HC0013

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6 JEE-Chemistry

BH3 THF HgSO 4 / H 2SO 4

14. B H 2O 2, OH
CH3–C CH A

A and B are –

O O
|| ||
(A) CH 3CH 2CHO, CH 3 C CH 3 (B) CH3 C CH 3 CH3CH 2CHO

(C) CH3CH2CHO (both) (D) CH3 C CH3 (both)

||
O
HC0014
CH 3 C NH 2
||
Mg / dry ether O
15. Br (X) (Y)
The structures of (X) and (Y) respectively are

(A) MgBr ; OH (B) ;

(C) MgBr ; (D) BrMg MgBr ; HO OH

HC0015

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

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 Hydrocarbon 7

EXERCISE # O-2
B2 D 6
1. CH3CH=CH2 H 2 O 2 / OH product X ; X is –

(A) CH3 CH CH 2D (B) CH3 CH CH 2OH

| |
OH D

(C) CH3 CH CH3 (D) none is correct

|
OD
HC0016
2. Aqueous solution of potassium propanoate is electrolysed. Possible organic products are:
(A) n-Butane (B) C2H5COOC2H5
(C) CH3–CH3 (D) CH2=CH2
HC0017
3. CH2 = CHCH2CH = CH2 NBS A, A can be

(A) CH 2 CHCHCH CH 2 (B) CH2=CHCH=CH–CH2Br

|
Br
(C) CH2 = CHCH2CH = CHBr (D) CH 2 CHCH 2C CH 2
|
Br
HC0018
4. Which of the following elimination reactions will occur to give but-1-ene as the major product?
EtOH EtOH
(A) CH3.CHCl.CH2.CH3 + KOH (B) CH3 .CH.CH 2 .CH3 NaOEt
|
NMe3

(C) CH3.CH2.CHCl.CH3+Me3COK+ (D) CH3.CH2.CH(OH).CH3 + conc. H2SO4

HC0019
OH—
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

5.

The above compound undergoes elimination on heating can yield which of the following products?

(A) (B) (C) (D)

HC0020

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8 JEE-Chemistry
6. Which of the following will give same product with HBr in presence or absence of peroxide.
(A) Cyclohexene (B) 1-methylcyclohexene
(C) 1,2-dimethylcyclohexene (D) 1-butene
HC0021
7. The ionic addition of HCl to which of the following compounds will produces a compound having
Cl on carbon next to terminal.
(A) CF3.(CH2)3.CH=CH2 (B) CH3.CH=CH2
(C) CF3.CH=CH2 (D) CH3.CH2CH=CH.CH3
HC0022
BH3 / THF HgSO 4
8. C A B
H 2O2 / OH – H 2SO 4

B & C are identical when A is –

(A) HC CH (B) CH3–C CH (C) CH3–C C–CH3 (D) CH3–CH2–C CH
HC0023
9. Match List-I with List-II and select the correct answer using the codes given below the lists:
List-I (Reaction) List-II (Reagents)
(A) CH3–CH=CH2 CH3–CHBr–CH3 (P) HBr
(B) CH3–CH=CH2 CH3–CH2–CH2Br (Q) Br2 / CCl4
(C) CH3–CH=CH2 BrCH2–CH=CH2 (R) HBr / Peroxide
(D) CH3–CH=CH2 CH3–CHBr–CH 2Br (S) NBS
HC0024
10. Column I (Reaction) Column II (Major product)
(i) BH3 / THF
(A) CH 3 C CH 2 (P) CH3–CH2–CH=CH2
| (ii) H2O2 / OH

CH 3

( i ) Hg ( OAc ) 2 / HOH
(B) CH 3 C CH 2 (Q) CH3–CH=CH–CH3
| (ii ) NaBH 4
CH 3
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Cl
|
CH 3ONa /
(C) CH 3 CH 2 CH CH 3 (R) CH 3 CH CH 2OH
|
CH 3

Cl OH
| ( CH3 )3 CONa
|
(D) CH 3 CH 2 CH CH 3 (S) CH 3 C CH 3
|
CH 3
HC0025

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 Hydrocarbon 9

EXERCISE # S-1
1. When n-butane is heated in the presence of AlCl3/HCl it will be converted into –
(A) Ethane (B) Propane (C) Butene (D) Isobutane
HC0026
OH
H (i) O3
2. A (ii)Zn / H 2 O Product(s). Product is/are?

CHO
(A) + HCHO (B) CH=O
O
O CHO
(C) + CH3CHO (D) O H C

HC0027

H3O Con. H 2SO 4 (i ) O3

3. + CH3MgBr A B (ii) Zn,H 2 O
C ; A, B and C aree –

A B C

O O
(A) CHO (B) CHO

CH3
O
(C) (D) CHO

HC0028
4. Which has least heat of hydrogenation –

(A) (B)
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(C) (D)

HC0029

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10 JEE-Chemistry

5. (±) reagent R 2 reagent R1

HO OH HO OH

R1 and R2 respectively are –

(A) Cold alkaline KMnO4, OsO4/H2O2
(B) Cold alkaline KMnO4, HCO3H / H3O+
(C) Cold alkaline KMnO4, CH3–O–O–CH3
(D) C6H5CO3H, HCO3H / H3O+
HC0030

O
18
(i) CH 3–C–O–O–H
6. + X
(ii) H 3O

The probable structure of ‘X’ is

(A) (B) (C) (D)

HC0031
7. Which alkene on heating with alkaline KMnO4 solution gives acetone and a gas, which turns lime
water milky –
(A) 2–Methyl–2–butene (B) Isobutylene
(C) 1–Butene (D) 2–Butene
HC0032
H CH3
C Cold alkaline KMnO4
8. A, which is true about this reaction?
C
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

H CH3

(A) A is meso 2, 3–butanediol formed by syn addition

(B) A is meso 2, 3–butanediol formed by anti addition
(C) A is a racemic mixture of d and l, 2, 3–butanediol formed by anti addition
(D) A is a racemic mixture of d and l 2,3–butanediol formed by syn addition
HC0033
9. Mixture of one mole each of ethene and propyne on reaction with Na will form H2 gas at S.T.P. –
(A) 22.4 L (B) 11.2 L (C) 33.6 L (D) 44.8 L
HC0034

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 Hydrocarbon 11
Lindlar ' s catalyst Na / NH 3
10. B R–C C–R A
A and B are geometrical isomers –
(A) A is trans, B is cis (B) A and B both are cis
(C) A and B both are trans (D) A is cis, B is trans
HC0035
11. A mixture of CH4, C2H4 and C2H2 gaseous are passed through a Wolf bottle containing ammonical
cuprous chloride. The gas coming out is
(A) Methane (B) Acetylene
(C) Mixture of methane and ethylene (D) original mixture
HC0036
12. Which of the following reagents cannot be used to locate the position of triple bond in
CH3–C C–CH3
(A) Br2/CCl4 (B) O3/H2O (C) Cu 2 Cl2/NH4OH (D) KMnO4/H
HC0037
13. In the presence of strong bases, triple bonds will migrate within carbon skeletons by the
(A) removal of protons (B) addition of protons
(C) removal and readdition of protons (D) addition and removal of protons.
HC0038

14. CH3–CH2–C CH CH3C C–CH3 ; A and B are –

(A) alcoholic KOH and NaNH2 (B) NaNH2 and alcoholic KOH
(C) NaNH2 and Lindlar catalyst (D) Lindlar and NaNH2 catalyst
HC0039
15. If a mixture of iso-octane (70%) & n-heptane (30%) is present in sample. The octane number of this
sample is :
(A) 40 (B) 70 (C) 30 (D) 85
HC0040
NH 4Cl
16. HC CH Cu 2 Cl2
Product

Product is –
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(A) Cu–C C–Cu (B) H2C=CH–C CH (C) HC C–Cu (D) Cu–C C–NH4
HC0041
17. Which of the following process is not good for the preparation of open chain alkane having odd
number of carbons :
(A) Wurtz process (B) Kolbe electrolysis
(C) Corey house synthesis (D) Both (A) & (B)
HC0042
18. How many moles of O2 required for complete combustion of one mole of propane –
(A) 7 (B) 5 (C) 16 (D) 10
HC0043

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12 JEE-Chemistry
19. How much volume of air will be needed for complete combustion of 10 lit. of ethane –
(Assuming that approx 20% O2 is present in air)
(A) 135 lit. (B) 35 lit. (C) 175 lit. (D) 205 lit.
HC0044

O sO 4 (1 eq )
20. X.
H 2O / Acetone

Identify ‘X’.

(A) (B)

(C) (D) Reaction will not occur

HC0045
A
21. Ph C CH 3 Ph–CH2–CH3
||
O
A could be:
(A) NH2NH2, glycol/OH–, (B) Zn(Hg)/conc. HCl

(C) Red P/HI (D) CH 2 CH 2 ; Raney Ni, H2,

| |
SH SH

HC0046
H 2 / Pt O3 / H 2 O
22. (A) C4H6 (B) C4H8 CH3COOH

Hence A and B are

(A) CH3C CCH3, CH3CH = CHCH3

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(B) CH2 = CHCH = CH2, CH3CH = CHCH3

(C) , CH3CH = CHCH3

(D) None
HC0047
23. An alkene on ozonolysis yields only ethanal. The ozonolysis of isomer of this alkene yields :

(A) Propanone (B) Ethanal (C) Methanal (D) Only propanal

HC0048

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 Hydrocarbon 13
24. Which is / are true statements/ reactions?
(A) Al4C3 + H2O CH4 (B) CaC2 + H2O C2H2
H
(C) Mg2C3 + H2O CH3C CH (D) Me3C–H + KMnO4 Me3C–OH
HC0049
25. Which reagent is the most useful for distinguishing compound I from the rest of the compounds
CH 3CH 2C CH CH3C CCH 3 CH3 CH2 CH2 CH 3 CH3CH=CH2
I II III IV
(A) Alk. KMnO4 (B) Br2/CCl4 (C) Br2/CH3COOH (D) Ammonical AgNO3
HC0050
26. Match the column
Column I Column II

(A) (P) Birch reduction

(B) (Q) Stephen’s reduction

(C) (R) Wolf-Kishner reduction

(D) (S) Clemmensen reduction

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

HC0051

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14 JEE-Chemistry
27. Match the column
Column I Column II
electrolys is
(A) RCOONa R–R (P) Correy-House reaction

NaOH,CaO
(B) R–CH2–COOH R–CH3 (Q) Kolbe electrolysis

( i ) AgNO 3
(C) RCOOH R–Cl (R) Oakwood degradration / Soda lime process
( ii ) Cl 2 /

(D) R’–X + R2CuLi R–R’ (S) Hunsdiecker reaction

HC0052
28. Column I Column II
(A) CH3–C C– CH3 cis-2-butene (P) Na/NH3(l)

(B) CH 3 C C CH 3 trans-2-butene (Q) H2/Pd/BaSO4

(C) CH3C C–CH3 1-Butyne (R) alc. KOH,

(D) CH3–CH3–C CH 2-Butyne (S) NaNH2 ,

HC0053

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

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 Hydrocarbon 15

EXERCISE # (J-MAINS)
1. 2-Methylbutane on reacting with bromine in the presence of sunlight gives mainly[AIEEE-2005]
(1) 2–bromo-2–methylbutane (2) 1–bromo-2–methylbutane
(3) 1–bromo-3–methylbutane (4) 2–bromo-3–methylbutane
HC0054
2. Alkyl halides react with dialkyl copper reagent to give [AIEEE-2005]
(1) alkyl copper halides (2) alkenes
(3) alkenyl halides (4) alkanes
HC0055
3. Reaction of one molecule of HBr with one molecule of 1,3–butadiene at 40°C gives predominantly
(1) 1–bromo–2–butene under thermodynamically controlled conditions [AIEEE-2005]
(2) 3–bromobutene under kinetically controlled conditions
(3) 1–bromo–2–butene under kinetically controlled conditions
(4) 3–bromobutene under thermodynamically controlled conditions
HC0056
4. Acid catalyzed hydration of alkenes except ethene leads to the formation of [AIEEE-2005]
(1) secondary or tertiary alcohol
(2) primary alcohol
(3) mixture of secondary and tertiary alcohols
(4) mixture of primary and secondary alcohols
HC0057
Me
5. Me OH
N
Et
n Bu

The alkene formed as a major product in the above elimination reaction is- [AIEEE-2006]
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Me Me
(1) Me
(2) CH2=CH2 (3) (4)

HC0058
6. Reaction of trans-2-phenyl-1-bromocyclo pentane on reaction with alcoholic KOH produces-
(1) 4-phenyl cyclopentene (2) 2-phenyl cyclopentene [AIEEE-2006]
(3) 1-phenyl cyclopentene (4) 3-phenyl cyclopentene
HC0059

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16 JEE-Chemistry
7. Phenyl magnesium bromide reacts with methanol to give- [AIEEE-2006]
(1) A mixture of anisole and Mg(OH)Br
(2) A mixture of benzene and Mg(OMe)Br
(3) A mixture of toluene and Mg(OH)Br
(4) A mixture of phenol and Mg(Me)Br
HC0060
8. Which of the following reactions will yield, 2, 2-dibromopropane [AIEEE-2007]
(1) CH3—C CH + 2HBr (2) CH3CH CHBr + HBr
(3) CH CH + 2HBr (4) CH3 — CH CH2 + HBr
HC0061
9. In the following sequence of reactions, the alkene affords the compound ‘B’ :- [AIEEE-2008]
O3 H 2O
CH3CH=CHCH3 A Zn
B.

The compound B is
(1) CH3CH2CHO (2) CH3COCH3 (3) CH3CH2COCH3 (4) CH3CHO
HC0062
10. The hydrocarbon which can react with sodium in liquid ammonia is [AIEEE-2008]
(1) CH3CH2CH2C CCH2CH2CH3 (2) CH3CH2C CH
(3) CH3CH=CHCH3 (4) CH3CH2C CCH2CH3
HC0063
11. The treatment of CH3MgX with CH3C C–H produces [AIEEE-2008]
H H
(1) CH3–CH=CH2 (2) CH3C C–CH3 (3) CH3—C = C —CH3 (4) CH4
HC0064
12. The main product of the following reaction is [AIEEE-2010]
C6H5CH2CH(OH)CH(CH3)2 Conc. H2SO4 ?

H5C6CH2CH2 H5C6 H
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(1) C = CH2 (2) C=C

H3C H CH(CH3)2

C6H5CH2 CH3 C6H5 CH(CH3)2

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

HC0065
13. 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]
(1) Ethene (2) Propene (3) 1-Butene (4) 2-Butene
HC0066

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 Hydrocarbon 17
14. Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the
presence of :- [AIEEE-2011]
(1) an isopropyl group (2) an acetylenic triple bond
(3) two ethylenic double bonds (4) a vinyl group
HC0067
15. Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar mixture.
Identify 'A' from the following compounds :- [AIEEE-2011]
(1) 2-Methyl-1-pentene (2) 1-Pentene
(3) 2-Pentene (4) 2-Methyl-2-pentene
HC0068
16. 2–Hexyne gives trans–2–Hexene on treatment with :- [AIEEE-2012]
(1) LiAlH4 (2) Pt/H2 (3) Li/NH3 (4) Pd/BaSO4
HC0069
17. In the given transformation, which of the following is the most appropriate reagent ? [AIEEE-2012]

CH=CHCOCH3 CH=CHCH2CH3
Re agent

HO HO

(1) NaBH4 (2) NH2 NH2, OH (3) Zn – Hg / HCl (4) Na, Liq.NH3
HC0070
18. The major organic compound formed by the reaction of 1, 1, 1–trichloroethane with silver powder
is :- (JEE MAIN OFFLINE 2013)
(1) 2-Butyne (2) 2-Butene (3) Acetylen (4) Ethene
HC0071

19. The number and type of bonds in C22 ion in CaC2 are: (JEE MAIN ONLINE 2014)

(1) Two bonds and one – bond (2) Two bonds and two – bonds
(3) One bond and two – bonds (4) One bond and one – bond
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

HC0072
20. In the hydroboration - oxidation reaction of propene with diborane, H2O2 and NaOH, the organic
compound formed is : (JEE MAIN ONLINE 2014)
(1) CH 3CH 2CH 2OH (2) (CH3)3COH (3) CH 3CHOHCH3 (4) CH3CH2OH
HC0073
21. Which one of the following class of compounds is obtained by polymerization of acetylene ?
(JEE MAIN ONLINE 2014)
(1) Poly-ene (2) Poly-yne (3) Poly-amide (4) Poly-ester
HC0074
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18 JEE-Chemistry
22. The gas liberated by the electrolysis of Dipotassium succinate solution is :
(JEE MAIN ONLINE 2014)
(1) Ethyne (2) Ethene (3) Propene (4) Ethane
HC0075
23. The reagent needed for converting (JEE MAIN ONLINE 2014)
Ph H
Ph–C C–Ph C =C
H Ph

is :
(1) H2/Lindlar Cat. (2) Cat. Hydrogenation
(3) LiAlH4 (4) Li/NH3
HC0076

24. CH2–CH=CH2 on mercuration- demercuration produces the major product :-

(Jee Main online 2014)

CH2–CH–CH3 CH2–CH2–CH2–OH
(1) (2)
OH

(3) CH2–COOH (4) CH2–CH–CH2

OH OH
HC0077
25. The major product obtained in the photo catalysed bromination of 2-methylbutane is :-
(Jee Main online 2014)
(1) 2-bromo-2-methylbutane (2) 2-bromo-3-methylbutane
(3) l-bromo-2-methylbutane (4) l-bromo-3-methylbutane
HC0078
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

26. In the presence of peroxide, HC and HI do not give anti-Markownikoff s addition to alkenes because
(1) All the steps are exothermic in HCl and HI (Jee Main online 2014)
(2) One of the steps is endothermic in HCl and HI
(3) HCl is oxidizing and the HI is reducing
(4) Both HCl and HI are strong acids
HC0079

E
 Hydrocarbon 19
27. Which compound would give 5-keto-2-methyl hexanal upon ozonlysis? (Jee Main offline 2015)

CH3 CH3 CH3 CH 3

H 3C CH3
(1) (2) (3) (4)
CH3 CH 3

HC0080
28. The major product of the following reaction is (Jee Main (Jan) 2019)
Br
KOH alc (excess)
Ph
Br

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

Ph Ph Ph
Ph
HC0081
29. Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of
light : (Jee Main (Jan) 2019)
C H3 C H2 C H C H2

(1) – hydrogen (2) – hydrogen (3) – hydrogen (4) – hydrogen

HC0082
30. The major poduct of the following reaction is: (Jee Main (Jan) 2019)
Cl
(i) HBr
(ii) alc.KOH

O
Cl Cl OH

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

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

OH O O O
HC0083
31. The major product of the following reaction is: (Jee Main (Jan) 2019)
CH3CH2CH–CH 2 (i) KOH alc.
(ii) NaNH2
Br Br in liq NH3

(1) CH3CH2C CH (2) CH3CH2CH–CH2

NH2 NH2
(3) CH3CH=C=CH2 (4) CH3CH=CHCH2NH2
HC0084

E
20 JEE-Chemistry
32. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product? (Jee Main (April) 2019)

(1) F3C – CH = CH2 (2) Cl – CH = CH2

(3) CH3O – CH = CH2 (4) H2N – CH = CH2

HC0085

33. The mojor product of the following reaction is : (Jee Main (April) 2019)

(1) CH3CD(Cl)CHD(I) (2) CH3CD2CH(Cl)(I)

(3) CH3CD(I)CHD(Cl) (4) CH3C(I)(Cl)CHD2
HC0086

34. The major product of the following addition reaction is : (Jee Main (April) 2019)

H3C – CH = CH2 Cl2 /H2 O

O
O
(1) CH3 – CH –CH 2 (2) H3C – CH –CH 2 (3) H 3C – (4)
| | | | H 3C CH3
Cl OH OH Cl
HC0087
35. But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by acidification will
give : (Jee Main (April) 2019)
(1) one molecule of CH3CHO and one molecule of CH3COOH
(2) CH3–CH–CH–CH 3
| |
OH OH
(3) 2 molecules of CH3COOH
(4) 2 molecules of CH3CHO
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

HC0088

E
 Hydrocarbon 21

36. The major product(s) obtained in the following reaction is/are : (Jee Main (April) 2019)

(i) KO t Bu
(ii) O3 /Me 2S
Br

OHC
(1)
CHO
CHO and OHC–CHO
(2)
OHC

OtBu
(3) OHC
CHO

(4) OHC CHO

HC0089
37. The major product [B] in the following sequence of reactions is :- (Jee Main (April) 2020)
(i)B2H6 dil. H2SO4
CH3 – C = CH – CH2 CH3 [A] [B]
(ii) H2O2,OH
CH(CH3)2

CH3–C–CH2CH2CH3 CH2=C–CH2CH2CH3
(1) (2)
C CH(CH3)2
H3C CH3

CH3–CH–CH=CH–CH3 CH3–C=CH–CH2CH3
(3) (4)
CH(CH3)2 CH(CH3)2
HC0090
38. The major product (Y) in the following reactions is : (Jee Main (April) 2020)
CH3
HgSO 4 ,H 2SO 4 ( i) C2 H 5 MgBr ,H 2 O
X Y
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

CH3 – CH – C CH H 2O ( ii) Conc. H 2SO 4 /

CH2 CH3
(1) H3C – C – CH – CH3 (2) CH3 – CH – C = CH – CH3
C2H 5 CH3
CH3 CH3
CH3 – C = C – CH3 CH3 – CH – C = CH2
(3) (4)
CH2CH3 CH2CH3
HC0091

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22 JEE-Chemistry
EXERCISE # JEE ADVANCE
1. Propyne and propene can be distinguished by – [IIT -2000]
(A) conc. H2SO4 (B) Br2 in CCl4 (C) dil. KMnO4 (D) AgNO3 in ammonia
HC0092
2. Which one of the following alkenes will react fastest with H2 under catalytic hydrogenation condition
[IIT -2000]

(A) (B) (C) (D)

HC0093
3. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti–Markovnikov
addition to alkene because – [IIT -2001]
(A) both are highly ionic (B) one is oxidising and the other is reducing
(C) one of the step is endothermic in both the cases (D) All the steps are exothermic in both cases
HC0094
4. The reaction of propene with HOCl proceeds via the addition of – [IIT ‘2001]
(A) H+ in first step (B) Cl+ in first step
(C) OH– in first step (D) Cl+ and OH– in single step
HC0095
Me Me
H
5. H
Me
H
Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives –
[IIT ‘2001]
(A) An optically active compound (B) An optically inactive compound
(C) A racemic mixture (D) A diastereomeric mixture
HC0096
6. Consider the following reactions – [IIT ‘2002]
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

H3C CH CH CH 3 + ‘X’ + HBr

| |
D CH3
Identify the structure of the major product ‘X’
• •
(A) H3 C CH CH CH 2 (B) H3C CH C CH 3
| | | |
D CH 3 D CH 3
• •
(C) H3C C CH CH 3 (D) H3 C C H CH CH3
| | |
D CH3 CH 2
HC0097

E
 Hydrocarbon 23
7. The nodal plane in the –bond of ethene is located in – [IIT ‘2002]
(A) The molecular plane
(B) A plane parallel to the molecular plane
(C) A plane perpendicular to the molecular plane which contains the carbon–carbon –bond
at right angle
(D) A plane perpendicular to the molecular plane which contains the carbon–carbon –bond
HC0098
8. Identify a reagent from the following list which can easily distinguish between 1–butyne and 2-butyne-
[IIT ‘2002]
(A) Bromine, CCl4 (B) H2, Lindlar catalyst
(C) Dilute H2SO4, HgSO4 (D) Ammonical Cu2Cl2 solution
HC0099
HgSO4
9. C6H5–C C–CH3 H 2SO4 A [IIT ‘2003]

(A) (B) (C) C6 H5 C CHCH 3 (D) C6 H 5 CH C CH 3

| |
OH OH
HC0100
x Br2
10. H 5 compounds of molecular formula C4H8Br2
( mixture)
H 2O

Number of compounds in X will be: [IIT ‘2003]

(A) 2 (B) 3 (C) 4 (D) 5
HC0101
11. 2–hexyne can be converted into trans–2–hexene by the action of : [IIT ‘2004]
(A) H2–Pd-BaSO4 (B) Li in liq. NH3 (C) H2–PtO2 (D) NaBH4
HC0102
12. Cyclohexene is best prepared from cyclohexanol by which of the following: [IIT ‘2004]
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(A) conc. H3PO4 (B) conc. HCl/ZnCl2 (C) conc. HCl (D) conc. HBr
HC0103
13. When Phenyl Magnesium Bromide reacts with tert. butanol, which of the following is formed?
(A) Tert. butyl methyl ether (B) Benzene [IIT ‘2005]
(C) Tert. butyl benzene (D) Phenol
HC0104

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24 JEE-Chemistry
14. 1–Bromo–3–chlorocyclobutane when treated with two equivalents of Na, in the presence of ether
which of the following will be formed? [IIT ‘2005]

(A) (B) (C) (D)

HC0105
15. CH3–CH=CH2 + NOCl P [IIT 2006]
Identify the adduct.

NO
|
(A) CH3 CH CH 2 (B) CH3 CH CH 2 (C) CH 3 CH 2 CH (D) CH 2 CH 2 CH 2
| | | | | | |
Cl NO NO Cl Cl NO Cl
HC0106
16. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT 2007]
(A) 1 (B) 2 (C) 3 (D) 4
HC0107
17. The number of structural isomers for C6H14 is [IIT 2007]
(A) 3 (B) 4 (C) 5 (D) 6
HC0108
18. The reagent(s) for the following conversion, [IIT 2007]
?
H H

is / are
(A) alcoholic KOH
(B) alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(D) Zn / CH3OH
HC0109
19. 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-2010]
(A) BrCH2CH2CH2CH2CH3 and CH3CH2C CH
(B) BrCH2CH2CH3 and CH3CH2CH2C CH
(C) BrCH2CH2CH2CH2CH3 and CH3C CH
(D) BrCH2CH2CH2CH3 and CH3CH2C CH
HC0110

E
 Hydrocarbon 25

20. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown
in the figure. [IIT-2014]

I and II an d III

The correct order of their boiling point is

(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
HC0111
Paragraph For Question 21 and 22
Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major
products formed in each step for both the schemes. [IIT-2014]

1. NaNH2(excess)
2. CH3CH2I (1 equivalent)
H X Scheme-1
HO 3. CH3I (1 equivalent)
M 4. H2 , (Lindlar catalyst)

1. NaNH2(2 equivalent)
OH
2. Br
H Y Scheme-2
3. H3O (M ild )
N 4. H2 , Pd/C
5. CrO3

21. The product X is -

H3CO H

(A) (B)
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

H
H H H3CO

CH 3CH 2O H

(C) (D)
H
H H CH3CH2O

HC0112

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26 JEE-Chemistry
22. The correct statement with respect to prodcut Y is -
(A) It gives a positive Tollens test and is a functional isomer of X
(B) It gives a positive Tollens test and is a geometrical isomer of X
(C) It gives a positive Iodoform test and is a functional isomer of X
(D) It gives a positive Iodoform test and is a geometrical isomer of X
HC0113
23. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are) [IIT-2015]
H Br
H Br H Br Br H
H 2C CH3 H 2C H 2C CH3
(A) H3C CH3 (B) (C) CH3 (D)

CH3
Paragraph For Questions 24 and 25
In the following reaction [IIT-2015]
Pb-BaSO4 (i) B2H6
C8H6 C8H 8 X
H2 (ii) H2O2, NaOH, H2O

H2O
HgSO4, H2SO4

(i) EtMgBr, H2O

C8H8O + Y
(ii) H , heat

HC0114
24. Compound X is :
O OH
CH3 OH CHO
CH3
(A) (B) (C) (D)

HC0115
25. The major compound Y is :
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

CH3 CH3
(A) (B)

CH2 CH3
CH3
CH3
(C) (D)

HC0116

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 Hydrocarbon 27
26. In the following reaction, the major product is - [IIT-2015]
CH3
1 equivalent HBr
CH2
H2 C
CH3 CH3 CH3 CH3
CH3 CH2
(A) CH2 (B) H3C (C) H2C Br (D) H3C Br
Br Br

HC0117
27. The number of hydroxyl group(s) in Q is [IIT-2015]
H
H
+
aqueous dilute KMnO4 (excess)
P Q
heat 0°C
HO
H3C CH3
HC0118
28. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [IIT-2018]
O heated iron tube
Conc. H2 SO4
(A) (B) Me H
873 K

O
1) Br2, NaOH CHO
+
2) H3O
(C) 3) sodalime, (D) Zn/Hg, HCl
OHC CHO
O O
HC0119
29. Which of the following reactions produce(s) propane as a major product?
(A) H3C electrolysis [IIT-2019]
COONa + H2O
(B) H3C COONa
NaOH, CaO,

(C) H3C Cl Zn, dil. HCl

Br
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

(D) H3C Br Zn

HC0120
30. Choose the correct option(s) that give(s) an aromatic compound as the major product.
H3C i) alc.KOH
ii) NaNH 2
Br
(A) + Cl 2 (excess) UV, 500K
(B) iii) red hot iron tube,873 K

Br

Br
NaOEt NaOMe
(C) (D) [IIT-2019]

HC0121

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28 JEE-Chemistry
ANSWER-KEY
EXERCISE # O-1
1. (A) 2. (C) 3. (B) 4. (C)
5. (C) 6. (B) 7. (A) 8. (D)
9. (D) 10. (C) 11 (D) 12 (C)
13 (C) 14 (B) 15. (C)
EXERCISE # O-2
1. (B) 2. (A,B,C,D) 3. (A,B) 4. (B,C)
5. (B,C,D) 6. (A,C) 7. (A,B,D) 8. (A,C)
9. (A) P ; (B) R ; (C) S ; (D) Q 10. (A) R ; (B) S ; (C) Q ; (D) P
EXERCISE # S-1
1. (D) 2. (B) 3. (A) 4. (C)
5. (B) 6. (A) 7. (B) 8 (A)
9 (B) 10 (A) 11 (C) 12 (A)
13 (C) 14 (A) 15 (B) 16 (B)
17. (D) 18. (B) 19. (C) 20. (B)
21. (A,B,C,D) 22. (A,B) 23. (A,B,C) 24. (A,B,C,D)
25. (D) 26. (A) S ; (B) R ; (C) P ; (D) R,S
27. (A) Q ; (B) R ; (C) S ; (D) P 28. (A) Q ; (B) P ; (C) S ; (D) R
EXERCISE # J-MAINS
1. (1) 2. (4) 3. (1) 4. (1) 5. (2)
6. (4) 7. (2) 8. (1) 9. (4) 10. (2)
11. (4) 12. (2) 13. (4) 14. (4) 15. (4)
16. (3) 17. (2)
18. (1)
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Cl Cl
CH3–C–Cl + 6Ag + Cl–C–CH 3 CH3–C C–CH3
Cl Powder Cl But-2-yne

19. (3)
+2
Ca [C C]–2
20. (1)
B2H 6/THF
CH3–CH=CH 2 – CH3–CH2–CH2
H2O 2/OH
OH
21. (2)
Polymerisation
nHC CH —CH=CH— n
yne poly-yne

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 Hydrocarbon 29
22. (2) 23. (4)
24. (1)

HgOAC
Hg(OAC)2
Ph–CH2–CH=CH2 Ph–CH2–CH–CH2
H2O
(oxymercuration) OH
NaBH4
Mechanism (Demercuration)
Good leaving group
Ph–CH2–CH–CH3
O
OH
O–C–CH3
Hg
O–C–CH3
O : HgOAC
Ph–CH2–CH=CH2 Ph–CH2–CH–CH 2
OAC
Hg
Ph–CH2–CH—CH2
Non-classical carbocation
..
H2O
HgOAC
NaBH4
Ph–CH2–CH–CH3 Ph–CH2–CH–CH2
OH OH

Rearrangement of carbocation formed is not possible due to formatiion of cyclic non-classical carbocation.
25. (1)

CH3 CH3
Br2/hv
CH3–CH–CH 2–CH3 CH3–C–CH2–CH3
Br (Major product)
2-Bromo-2-methyl butane
CH3
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

Br-CH2–CH–CH2–CH3
CH3 Minor
CH3–CH–CH–CH3 products

Br
CH3
CH3–CH–CH2–CH2–Br

Relectivity ratio for bromination is

1° : 2° : 3° : : 1 : 82 : 1600
Hence 3° product will be major product.
26. (2)

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30 JEE-Chemistry
27. (4)
CH3 6CH
3
5 O
Ozonolysis 4
O
3 1
2
CH3
CH3
5-Keto-2-Methylhexanal
28. Ans. (3) 29. Ans. (2) 30. Ans. (1) 31. Ans. (1)
32. Ans. (1) 33. Ans. (4) 34. Ans.(2) 35. Ans. (3)
36. Ans. (2)
37. Ans. (1)
OH
(i) B2H 6
Sol. CH3–C=CH–CH2–CH3 H3C–CH – CH–CH2–CH3
–
(ii) H2O2/OH
CH(CH3)2 CH(CH3) 2

dil. H 2SO4/ –H2O

–
1, 2 shift of H
H3C–C – CH2–CH2–CH3 H3C–CH – CH–CH2–CH3
CH3 CH(CH3) 2
HC
CH3
–
1, 2 shift of H
H3 C CH2–CH 2–CH3
+ C
–H (Saytzeff product
H3C–CH – CH2–CH2–CH3 Major product)
C
C H3 C CH3
H3 C CH3

38. Ans. (3)

CH3
Sol. CH3–CH–C CH
HgSO4, H 2SO 4
(X)
H2O
(i) C2H5 MgBr, H2O
(ii) Conc. H2SO4/

(Y)
node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65

O
HgSO 4, H 2SO 4
CH3–CH–C CH H2O CH3–CH–C–CH3
CH3 (Kucherov's CH3
Reaction) (X)
C 2H5 MgBr, H 2O
(Nucleophilic addition
reaction)
OH
+
H/
CH3–C C–CH 3 CH3–CH–C–CH3
CH3 CH2–CH3 CH3 CH2–CH3
Major
(Saytzeff alkene)

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 Hydrocarbon 31

EXERCISE # JEE ADVANCE

1. (D) 2. (A) 3. (C) 4. (B) 5. (B)
6. (B) 7. (A) 8. (D) 9. (A) 10. (B)
11. (B) 12. (A) 13. (B) 14. (D) 15. (A)
16. (A) 17. (C) 18. (B) 19. (D) 20 (B)
21. (A) 22. (C) 23. (B,D) 24. (C) 25. (D)
26. (D) 27. (4)
28. (A,B,D)

ConcH 2SO 4
Sol. (A) (B) Fe

(1)Br2 NaOH (3)Soda lim e

(C) (2)H 3O

(D) ZnHg,HCl

29. Ans. (B,C) 30. Ans. (B,D)

node06\B0B0-BA\Kota\JEE(Advanced)\Enthuse\Chem\Sheet\Hydrocarbon\Eng.p65