1156 Hydrocarbon

1. Which one of the following alkenes will react fastest with H under 2 CH 3 CH 2 Cl
catalytic hydro-genation condition
(b)  Cl 2  
boiling
[IIT-JEE (Screening) 2000; CBSE PMT 2005]

R R R H CH 3
(a) (b) (c)  CH 3 Cl 

anh. AlCl3

H H R H
R R R R
(c) (d) CH 2 Cl CH 2 NO 3
(d)  AgNO 2 
H H R R
2. On cracking petrol, we get [CPMT 1980]
(a) CH 4 9. The most unlikely representation of resonance structures of p-
nitrophenoxide ion is [IIT-JEE 1999]
(b) C3 H 6 –O
– O O
(c) Both (a) and (b) N (–)
(d) CH 3  CH 4  C 2 H 6  alcohols (a) (b)
3. Cetane is a compound which has very good ignition property.
Chemically it is [CPMT 2004]
N
(a) CH 3 (CH 2 )14 CH 3 O + O–
O–
(b) (CH 3 )3 C(CH 2 )11 CH 3 O + O O
(c) N (d)
(c) C17 H 34
(d) None of these
4. Which one of these is not compatible with arenes
[CBSE PMT 1998] 10. Which one of the following on ozonolysis Nfollowed by oxidation will
–O + O–
(a) Greater stability give adipic
O–acid [AMU 2002]
CH 3
(b) Delocalisation of   electrons
(c) Electrophilic additions (a) (b)
(d) Resonance
5. Which of the following is an electrophile [BHU 1998]
CH 3
(a) H 2O (b) NH 3
(c) (d)
(c) AlCl3 (d) C 2 H 5 NH 2
6. The reaction,
11. Which of the following structures correspond to the product
H 2 C  CH 2  H 2O 3   C2 H 5 OH
H PO
4
expected, when excess of C 6 H 6 reacts with CH 2 Cl 2 in presence
Ethylene water 300 C / 60 atm.. Ethyl alcohol
of anhydrous AlCl3 [CBSE PMT 1989]
is called : [Pb. CET 2001]
(a) Hydration (b) Sublimation
(a) CH (b) CHCl 2
(c) Dehydration (d) Substitution |
7. In reaction Cl
Cl
C6 H 5 CH 3    A 
Oxidation
 B 
NaOH
 C
Sodalime
|
Then C is [MP PET 2004] (c) C (d) CH 2
|
(a) C6 H 6 (b) C6 H 5 OH Cl
12. Which of the following will be easily nitrated [DCE 2001]

(c) C6 H 5 COON a (d) C6 H 5 ONa CH 3
8. Which one of the following is a free-radical substitution reaction [CBSE PMT 2003]
(a) (b)
(a) CH 3 CHO  HCN  CH 3 CH (OH )CN

(c) CH 3 NO 2 (d) C 6 H 5 NO 2
 Hydrocarbon 1157
13. Chlorination of benzene is not possible in the following reaction 17. An alkane (molecular
[UPSEAT 2004] weight 72) forms only one monochlorinated
product. Its formula is [BHU 1981]
(a) C6 H 6  Cl 2 
 FeCl3


(a) (CH 3 )4 C
(b) C6 H 6  HOCl 
H
 (b) CH 3 (CH 2 )3 CH 3
(c) C6 H 6  I  Cl  
ZnCl 2
(c) (CH 3 )2 CHCH 2 CH 3
(d) C6 H 6  Cl 2 
 AlCl3
CH 2
Hg 2  / H 
14. Ph  C  C  CH 3 
 A . A is (d) H 2C CH 2
[IIT-JEE Screening 2002]
H 2C CH 2
O 18. The poisonous gas that comes out with petrol burning in a car is
(a) Ph (b) Ph (a) CH 4 (b) C2 H 6
O
(c) CO 2 (d) CO
H 3C H3C
19. The reagent X in the reactions
OH (CH 3 )3 CCH  CH 2  Y 
X NaBH 4
THF NaOH
(c) Ph (d) Ph
OH (CH 3 ) 3  C  CH  CH 3
|
H3C H3C OH
15. In order to complete the reaction [Roorkee 2000]

1  Pentyne  4  Octyne  cis 4Octene a and b will
a b (a) H 3O
be (b) Hg(CH 3 COO)2
a b
(1) NaNH 2 ; CH 3 CH 2 Br : H 2 , (one mole) Pd or Ni (c) OH 
(2) NaNH 2 ; CH 3 CH 2 CH 2 Br : H 2 (two moles) Pd or Ni (d) HCOOH
(3) NaNH 2 ; CH 3 CH 2 CH 2 Br : H 2 , (one mole) Pd or Ni 20. CH 2  CH 2    A,
Br2 / H 2 O

In the above reaction the compound A is [DPMT 2004]

(4) NaNH 2 ; CH 3 CH 2 CH 2 Br : BH 3 , H 2 O 2 , OH  (a) Ethylene bromohydrin
[MP PET 1994] (b) 1, 2-dibromo ethane
(a) 1 (b) 2 (c) Ethanol
(c) 3 (d) 4 (d) None of these
16. The number of secondary hydrogens in 2, 2-dimethyl butane is [UPSEAT 2004]
(a) 8 (b) 6
(c) 4 (d) 2

(SET -24)

1. (a) According to saytzeff rule order of stability is R R R R

CC CC
R R R H
 1158 Hydrocarbon
R H R R
CC CC
R H H H
2. (c) On cracking petrol gives smaller hydrocarbons like CH , C H . 4 3 6

3. (a) Cetane is chemically hexadecane i.e,

CH 3 (CH 2 )14 CH 3 . H CH 3
4. (c) In arenes electrophillic substitution reaction takes place and it | |
does not gives electrophillic addition reactions. We also know 16. (d) H 3 C  C  C  CH 3
that benzene is a resonance hybrid of two structure’s and | |
greater stability of benzene is due to delocalization of H CH 3
π electron. 2,2 dimethyl butane

5. (c) AlCl3 is an electron deficient compound. Hence, act as an 17. (a) The alkane forms only one mono substituted product, it must
electrophile. have only one type of hydrogen atoms. there fore the alkane is
6. (a) Alkenes react with water in the presence of acid and form 2, 2-dimethyl propane.
alcohols. This reaction is called as hydration. 18. (d) On petrol burning CO comes out which is so much poisonous
H H gas.
| | 19. (b) Oxy mereuration-demercuration : with mercuricacetate (in
H  C  C  H  H 2 O   H  C  C  H
H 3 Po 4
THF) followed by reduction with NaBH 4 / NaOH is an
| | 300 C / 60 atn | |
H H H H example of hydration of alkene according to markowni koff’s
Ethylene Ethyl alcohol rule.
7. (a) C6 H 5 CH 3 
 C6 H 5 COOH 
[O ]
 NaOH
(CH 3 )3 C  CH  CH 2  (CH 3 )3 C  CH  CH 2  HgOOCCH 3
(CH 3 COO )2 Hg
[ A] THF |
OOCCH 3
C6 H 5 COONa  C6 H 6 NaOH / CaO

[ B] [C ] NaBH 4 / NaOH
8. (b) Halogenation of alkyl group proceed via free radical (CH 3 )3 C  CH  CH 3
mechanism. |
OH
3, 3 - Dimethyl- 2 - butanol
O
 Br , H O
9. (c) The structure O is most unlikely
N 20. (a) CH 2  CH 2 2
2
 C H 2  C H 2
O | |
Br OH
as N containing 5 valence electrons should not carry positive Ethylene bromohydrin
charge.
Hence compound A is Ethylene bromohydrin.
CH 3

CH 3
|
10. (b) 
 OHC  (CH 2 )3 CH  CHO 
O3

[O ]

CH 3
|
HOOC  (CH 2 )3  CH  COOH
Substitute d adipic acid

11. (d)  CH 2Cl 2    

Anhydrous AlCl3

CH 2  2 HCl
Diphenylmethane
12. (a) The presence of an electron-releasing groups (+I group) e.g.,
CH 3 ,OH, NH 2 etc makes the process of nitration easier.
So C6 H 3 CH 3 will be easily nitrated.
***
13. (b) Reaction is called Gattermann-Koch synthesis, which is carried
by catalyst AlCl3 .
O
||
14. (a) C 6 H 5  C  C  CH 3  C 6 H 5  C  CH 2  CH 3
HgSO 4
H 2 SO 4

NaNH
15. (c) CH 3  CH 2  CH 2  C  CH 
2

CH CH CH Br
CH 3  CH 2  CH 2  C  C  Na 
3
2
2

H
CH 3  CH 2  CH 2  C  C  CH 2  CH 2  CH 3 
2

4 Octyne Pd
CH  CH
CH 2 CH 2
CH 2 CH 2
CH 3 CH 3
cis-4-Octene