BAKLIWAL TUTORIALS

Organic Chemistry assignment Topic: Hydrocarbons

EXERCISE - I
(Linked Comprehension type questions)
Comprehension - I
Alkane may be prepared from alkyl halide by wurtz method where alkyl halide reacted with Na in presence
of ether.
Ether
2R  X 
 R  R  2NaX
mechanism
R  X  2Na 
 RNa  NaX
R  X  RNa 
 R  R  NaX
Na / ether
1. CH 3 CH 2 Cl 


Which of the following may not be formed ?
a) CH3–CH3 b) c) CH2 = CH2 d) CH4

Ba / ether
2.  Br  
 major product

a) b) c) d) No reaction

3. Which of the following is most reactive for wurtz reaction ?

Br
Br Br
a) b) c) d) Br

Comprehension - II
Cycloalkanes stability can be explained by BST According to BST which ever cycloalkane having low
Bayer’s distortion that is more stable. Later on stability of cycloalkanes verified from heat as combustion
values. Heat of combustion is inversely proportional to stability
4. According to Bayer strain theory (BST) the decreasing order of stability is

a) > > > b) > > >

c) > > > d) All are equally stable

5. The most stable cycloalkane among the following is

a) b) c) d)

6. Bent bonds are present in

a) and b) and c) and d) and

BAKLIWAL TUTORIALS Reddy Sir

Comprehension - III
Hydroboration is a reaction in which the boron hydride acts as an electrophile, R 2BH adds to a carbon -
carbon double bond which acts as a nucleophile

+ R2BH
H C C BR2

Organoborance
compound

The organoborane compound then is oxidised by treatment with hydrogen peroxide in aqueous medium to
form alcohol. The OH group enters the carbon atom from the same side where the boron atom was
present.
Hence this reaction is highly regioselective and the boron atom attaches to that carbon atom which is less
sterically hindered.
Me

H
7. 
(1) B2 H 6
( 2) H 2O2 / OH
 A Hence compound A is

Me
H H HO H HO H Me HO

H H H H
OHMe H H H Me H H
a) b) c) d)
Me Me Me Me

8. R  CH  CH2 
 X Hence x is
NOCI

a)
R  CH  Cl b) R  CH  CH 2  Cl
| |
NO NO
c) R  CHO  CH 2Cl2 d) R  CH  CH 2 NO
|
Cl

9. R  CH  CH 2  CO  H 2 
[ Co2 ( CO )8 ]
 A Hence a is

a) R  CH 2CH 2CHO b) R  CH  CH 3 c) R  CH  CH  CHO d) Both (a) and (b)

|
CHO

BAKLIWAL TUTORIALS Reddy Sir

Comprehension - IV
Limonene (A) is a naturally occuring hydrocarbon with fragrance of lemons. When (A) is hydrogenated
over Pd/C it absorbs 2 moles equailvalent of hydrogen and produces 4- methyl -1 isopropylcyclohexane.
When (A) is treated with ozone, followed by reduction work up, two products are isolated : formaldehyde
and the diketone below

CHO
Hydrogenation of unknown compound (B) over Pd/C gives hexane, whereas hydrogenation over Lindlar’s
catalyst gives (C) Ozonolysis of (C) gives only C2H5CHO
10. Here compounds B and C are respectively
Et  CH  CH  Et ,
CH3CH2 H
a) C C b )
H CH2CH3

H3CH2C CH2CH3
Et  CH  CH  Et , C C
H H

Me Pr Me H
c) Me  CH  CH  Pr, CC d) Me  CH  CH  Pr C C
H H H Pr
11. Here compound A is

a) b) c) d)

12. When compound C is reacted with alkaline KMnO4 in cold conditions, it would give
a) Meso -hexane -3, 4 - diol b) Racemic mixture of 3,4 - dihydroxyhexane
c) only (+) form of 3,4 -dihydroxyhexane d) (-) from of 2,3 - dihydroxyhexane
Comprehension - V
oxymercuration demercuration reaction is process of addition H2O according to Markownikoffs rule without
any rearrangement
OH
|
Hg(OAC) 2 ;H 2O
CH 3  CH  CH 2   CH 3  CH  CH 3
NaBH 4 ;OH

BAKLIWAL TUTORIALS Reddy Sir

 CH3
Hg(OAC)2 ;H 2 O
13. C  CH 2   major product is
NaBD4 ; OH
CH3 CH3 CH3 CH3
a) ph  C  CH3 b) ph  C  CH 2 D c) ph  C  CH 2OH d) ph  C  CH 2 D
OH OH D OD
CH 3
Hg(OAC) ;CH OH
14. CH 3  C  CH  CH 2 
2 3
 product
NaBH 4 ,OH
CH 3
OCH 3 CH 3 CH3 OH CH3 OCH3
a) CH 3  C  CH  CH 3 b) CH 3  C  CH  CH 3 c) C H 3  C  C H  C H 3 d) no reaction
CH 3 CH3 CH3

NH 2 Hg(OAC) 2
15.    
NaBH 4 ;OH

OH H
NH 2 N–H N
a) b) c) d) Both ‘A’ and ‘B’

Comprehension - V

alc.KOH Br2 NaNH 2

(X) (C 4 H 9 Br)    ' Y '  ' Z '(Dibromide)    ' W ' gas

White ppt.
AgNo 3
solution

16. ‘X’ ‘Y’ and ‘Z’ are

‘X’ ‘Y” ‘Z’
Br
|
a) CH3CH2CH2CH2Br CH3 – CH = CH – CH3 CH 5  CH  CH 2 CH 2  Br

Br Br
| |
b) CH3CH2CH2CH2 - Br CH3CH2–CH = CH2 CH 3  CH 2  CH  CH 2

Br Br Br
| | |
c) CH 3  CH  CH 2  CH 3 CH3 – CH = CH – CH3 CH 3  CH  CH  CH 3

Br Br Br
| | |
d) CH 3  CH 2  CH  CH 3 CH3 – CH2 – CH = CH2 C H 3  C H 2  CH  CH 2

BAKLIWAL TUTORIALS Reddy Sir

17. Reductive Ozonlysis of ‘Y’ yields
a) 2 moles and CH3CHO b) CH3CH2CHO and HCHO
O O
|| ||
c) CH 3  C  CH 3 and H  C  H d) CH3CH2 – COOH and HCOOH

18. Which of the following statement (s) is are correct

a) compound ‘W’ has 2 degree of unsaturation
b) ‘Y’ and ‘W’ are functional isomers
c) ‘W’ can be converted into ‘Y’ with Na/Liq NH3
d) ‘W’ can be converted into ‘Y’ with Ni/Pt
Comprehension - VI
Addition of ozone on alkene is an example of 1,3 - dipolar addition reaction. The product of addition
reaction is molozonide which undergoes rearrangement to give ozonide
O
+ -
R  CH  CH  R  O O R  CH  CH  R 
Re arrangement
II
 R  CH CH  R
O O
O O
O
O Ozonide
Molozonide

H 2O / Zn
IV III H 2O

R  CH  O R  COOH
Addition of ozone followed by hydrolysis in the presence of reducing agent is known as reductive
ozonolysis while ozonolysis in absence of Zn is knwon as oxidative ozonolysis
19. Which of the following is the slowest step in ozonolysis
a) step - I b) step - II c) step - III d) step - IV
20. The ozonolysis product of enol form of cyclobut -1, 3 -diene -1, 3 -diol is
a) glyoxal b) glycol c) oxalic acid d) glycollic acid

21. CH 3  C  CH 
O3 / Zn
HOH
 A 
N3OH
0 C
B The ‘B’ is
|| ||
CH  C  CH 3
OH O
| |
CH 3  CH  CH
a) | | b) c) CH 3  C H  C OOH d) C H 3  C  C H 3
CH  CH  CH 3

Comprehension - VII
Neither bromine nor ethylene is a polar molecule but both are polarizable and an induced dipole - induced
dipole force cause them to be mutually attracted to each other. this indued dipole - induced dipole attraction
site the stage for Br2 to act as an electrophile. Electron flow from the  system of ethylene to Br2 causing
the weak bromine - bromine bond to break.

BAKLIWAL TUTORIALS Reddy Sir

 
Br  Br
CH 2  CH 2   CH 2  CH 2 
Br
 Br  CH 2  CH 2  Br
+
Br
Bromonium ion

A carbocation of the type shown, however has been demonsrated to be less stable than an alternative
structure called cyclic bromonium ion. The addition of bromine to alkene is anti
addition reaction.


Br2
 ( A)
22. H 2O The compound ‘A’ is

H H OH

a) OH b) Br c) H d) None of these
Br OH Br
23. Addition of bromine on alkene is
a) stereoselective reaction only b) sterespecific reaction only
c) stereoselective as well as stereospecific reaction d) neither stereospecific nor stereoselective

24. 
NBS
NaBr
 gives

Br

Br
H Br H Br
a) b) c) H H
d) Br H

Br

EXERCISE - II (Match the Following Questions)

25. Matching
Column I Column II
Br
A) Br 
 p) Red P + HI
O
B) 
 q) Na/ether
OH OH

C) O 
 r) NH2 – NH2 / OH

COOH COO
D) 
 s) Zn -Hg/HCl

BAKLIWAL TUTORIALS Reddy Sir

26. Column - 1 Column - II
( Reaction) (Products)

A) Al4C3 + H2O 
 p)

CH I
B) CH3 – CH = CH2 2 2
ZnCu
q) CH4

O
Zn  Hg
C) 
HCl
 r)

Cr2O3  Al2O3 H 2 / Ni
D) H  0   0 s) H2O
600 C 200 C
t) cycloalkane
27. Column -I Column-II

CH3 CH CH2

A) CH3 CH CH2 CCl3 p) Markownikoff’s addition

Br
+
R3N - CH = CH2
B) + q) Anti Markownikoff’s addition
R3N - CH2 - CH2 -Br

C) CH3C CH CH3 C CH3 r) Electrophilic addition

D) CH3 CH CH CH3 s) Radical addition

CH3 CH CH2 CH3

Br
28. Column - I Column - II
A) CH2 = CH - COOH +HBr p) Non regioselective
B) cis CH3  CH  CH  C2 H5  KMno4
(cold alk.) q) trans addition
C) cis CH 3  CH  CH  CH 3  X 2  r) Primary carbocation
CS 2

Me

D) 
HCI
 s) Optically active
H

BAKLIWAL TUTORIALS Reddy Sir

29. Column - I (Reaction) Column - II (Type of reaction)
CH3 H3 C D
1)BD3THF
A) 
2)CH 3CO2 T
 p) T

CH3 H3C D
1) BT3 ;THF
B) 
2) CH 3CO 2 D
 q)

CH3 CH3
1) BD3 ;THF
C)   r) D
2) CH CO H
3 2

CH3 H3C T
1) BH 3 ;THF
D) 
2) CH 3CO 2 D
 s) D

30. Column - I Column - II

H 3C H
A) when reacts with Br2/CCl4 p)

diastereomer will formed

H 3C H
B) When react with O3/H2O2 q)

dicarboxylic acid will formed

H 3C H
C) Optically active compound r)

H 3C H
D) when undergo reductive ozonolysis s)

following product will be formed

H 3C H
H
O
H O

BAKLIWAL TUTORIALS Reddy Sir

31. Column - I Column - II
A) Alkyne  cis - Alkene p) Pt in quinoline
B) Alkyne  trans - Alkene q) P -2 catalyst (Nickel Boride) Ni 2B
C) Alkyne  Alkane r) Wilkinson’s catalyst
D) Alkene  Alkane s) Na in liquid NH3
32. Column - I Column - II


A) CH 3  CH  C  CH 3  
HOH / H
P) C6 H 5  CH  CH 2  CH 3
|
CH 3
CH 2
B) Q) CH 3  CH  CH  CH 3

NBS

|
.C HCH 3

2
H  Br
C) CH 2  CH  CH  CH 3 
 R)
|
CH 3

S) CH 3  CH 2  CH  CH 3

D) 
HOH / H

|
CH 3

EXERCISE - III (Integer answer type Questions)

33. Sodium isovalerate on electrolysis give ‘X’ the No . of 30 H in ‘X’ are
O
C Oet
1) etO Na N 2 H 4 / KOH

2) KOH
 ' X '   'Y '
34. 3) 
C Oet
O
The sum of oxygen atoms in X and Y (x + y) are
35. Select the compounds which will give more no.of monochloroderivaties than 2,2,3,3 tetra methyl butane on
treatment with Cl2/h
Ethane : Propane : isobutane; isopentane; pentane; methane; 2, 2-dimethyl pentane ; 3 methyl pentane;
cyclopentane ; 2,3 dimethyl butane
36. The no. of structral isomers for C7H16
37. What is the number of carbons present in a lightest alkane molecule which is optically inactive due to
internal compensation.
38. The weight (in grams) of hydrocarbon produced when 9.6 grams of sodium propanoate is heated with
sodalime is

39. (Limonene) on ozonolysis gives A(main) which on reation with Zn/Hg in Conc.Hcl gives Compound

‘B’. No of methyl groups present in the molecule of B is

BAKLIWAL TUTORIALS Reddy Sir

40. Number of carbon atoms in the cyclo alkane ring which has the angle strain 9.750 is
1equi HOCl
41. 
NBS
 'A '   'B '
Number of optical active isomers in ‘B’ are.
Br
42.  alc.KOH
 O
 ' A '  Zn 3
  ' B '  2
HC N
 ' C '
(m ajor) / H 2 O
'D'
H 3O

The number of oxygen atoms in ‘D’ are

AgOH
43. N I 
 the number of  -Hydrogens in the product are

Br2 alc.KOH
44. 2,3 dimethyl butane 
hv
(A)   ' B'
major (major)

Na Cl h  N 2H 4
'E' 2  ' D ' 
KOH
 2C O 3 / M e 2S
Dry ether (minor)

Cr O
'F' 
2 3
0 
 'G '
Al 2 O3 / 600 C
AlCl
E + G 
3
(H) major
The number I0H (H) are
Pd  BaSO 4 Alkaline
45. CH3C  CCH3   'A ' 
KMnO
 'B' no.of optical active isomers in ‘B’ are
4

1equi. C H OH
46. Br F 
Mg / ether
 'A ' 
2 5
 'B'(organiccompound) no. of carbons in ‘B’ are

HO COOH
47. C  C H no.of moles of CH3MgBr is used to get –moles of CH4
HO NO2
48. Number of  bonds in acrylonitrile are ---

BAKLIWAL TUTORIALS Reddy Sir

 EXERCISE - I
1) d 2) a 3) b 4) b 5) a 6) c 7) c 8) d 9) d 10) b

11) d 12) a 13) b 14) c 15) b 16) b 17) b 18) a 19) d 20) b

21) c 22) c 23) c 24) d

EXERCISE - II
25) A - q; B - r; C - prs; D - qr 26) A - q; B - pt; C - st; D - st
27) A - qs; B - qr; C - pr; D - rs 28) A - r; B - s; C - qs; D - ps
29) A - p ; B - s; C - q ; D - r 30) A - pqrs; B - pq ; C - pqrs ; D - q
31) A - pq ; B - s; C - r ; D - r 32) A - qs; B - r ; C - qs ; D - p

EXERCISE - III
33)2 34) 1 35) 6 36) 9 37) 8 38) 3 39) 3 40) 4 41) 4 42) 6
43) 2 44) 6 45) 0 46) 4 47) 4 48) 3

BAKLIWAL TUTORIALS Reddy Sir

 HOME TEST - 1 PRACTICE TEST
SECTION - A
Single correct answer Type Questions
CH 3 CH 3
1. 
 reagent used for reaction

a) LiAlH4 b) H2/Ni c) NaBH4 d) H2/Pd/CaCO3.

2. 1-Methylcyclopentene can be converted into the given compound
D
by use of following reagent
CH3
a) BD3 followed by CH3COOH b) BH3 followed by CH3COOD
c) BD3 followed by CH3COOD d) BH3 followed by CD3COOH
3. Rate of hydrohalogenation of the following alkenes is

CH = CH CH3 – CH = CH
I II
CH3
CH3 – C – CH = CH2
CH3 – C – CH – CH3
CH3
IV
III
a) I > III > II > IV b) II > I > III > IV c) II > I > IV > III d) I > II > IV > III
4. Arrange in decreasing order of reactivity with HCl

NO2 OCH3
I II III
a) II > III > I b) III > II > I c) III > I > II d) None of the above
OH
H
5. The product of the following reaction can be : H3C CH = CH2 
CH3 CH3

a) H3C OH b) OH c) d) H3C O

O
CH3 CH3 CH3 CH3
H CH3
Br
2
CCl4
 X
6. (stereoisomer) X may be
C2H5
(Z) 
BAKLIWAL TUTORIALS Reddy Sir
Br
 Br Br
Br Br

H Br H3C Br
a) b) Br Br c) Br H d)
H5C2 Br H5C2 Br
H5C2 H H5C2 Br
CH3 H
CH3 CH3
7. cis-2-Butane 
HOBr

CH3 CH3 CH3 CH3
H OH H OH H3C OH H3C Br
a) b) c) d)
H Br Br H Br H HO H
CH3 CH3 H H
(1) HBr (2 moles) (2) Zn
8. 
R O
 A 
Ether
 B ; Give the molecular weight of B
2 2

a) 135 b) 140 c) 138 d) 133

H
9. N
 A ; A is
Br
2

H Br
Br N
N N
a) b) N c) d)
Br
10. In the given BrBrH (Excess) 
Br reaction CH  C  CH  O  CH  CH  O HCl
 X(Major)
3 3 3

CH3
The X will be :
OCH3
|
CH 3  C  CH 2  OCH 3 OCH3
a) | b) CH 3  CH  CH
CH3 OCH3
CH3
Cl Cl
| .. | ..
CH 3  C  CH 2  O  CH 3 CH 3  CH  CH  O  CH 3
c) | .. d) | ..
CH3 CH3
SECTION - B
More than one correct answer Type Questions
11. Which are correct regarding Boiling point ?
H3C CH3 H3C H H3C Cl H3C H
a) > b) <
H H H CH3 H H H Cl
Cl Cl CH 3 CH3
Cl Cl
> d) >
c)

Cl Cl
H 3C Br
12. C=C  CH3  C  C  CH3

Br CH3

BAKLIWAL TUTORIALS Reddy Sir

 Which of the following reagents can be used for above convertion ?
a) Zn /  b) Mg/  c) NAi / Acetone d) AlC KOH
13. Which of the following reactions give meso product ?
H3 C H H3 C CH3
Br2 / Ccl4
a)  b) cold.KMnO4
 
H CH3 H H
H3 C H
c) 
Br / H O
 d)
Br2
 
CCl
H CH3 2 2 4

14. Which of the following reaction give diastereomeric products ?

H3 C CH3
Br2 / H 2O Br2 / CCl 4
a)   b)  
H H
CH3 Br

m  CPBA H3 C H
   OsO 4
c) H 3O
d)  
H CH3
H3 C CH2–CH3

15. Mark out correct comparisons.

a) 3o > 2o H > 10 H(reactivity for bromination) b) < CH2 (stability)

c) < CH2 (reactivity towards HBr )

d) > CH2 ( reactivity for catalytic hydrogenation)

16. Which of the following conformer of cyclohexane is more stable than half- chair ?
a)Boat b) Twist boat c) Chair d) Half chair

SECTION - C
Linked Comprehension Type Questions
Comprehension - I
Acidifiation of HX on alkene proceed through formation of carbocation.This reaction is also known as
Markownikhoff’s reaction. According to MK rule addition of electrophile occurs on that carbon of alkene
which have more number of –H atom.
X
|
ph  CH  CH 2 
HX
 ph  CH  CH 3  ph  CH 2  CH 2  X
major (minor )
17. Which of the following alkenes can produce diastereomers

a) CH 3  CH  CH  CH 3 b) CH  CH  CH 3

BAKLIWAL TUTORIALS Reddy Sir

 H CH3
CH3
c) d) CH3–CH=CH2

18. Which of the following alkenes will give Markownikhoff’s reaction ?

HCl 
a) F3C  CH  CH 2   HCl
b) H3 N  CH  CH 2  
CH 3 HBr
HBr
c) O 2 N  CH  CH 2   d) C  CH 2  
H 3C
19. Arrange the following alkenes in decreasing order of reaction with HBr.

H3C
CH 3 H 3C C  CH 2

:
C  CH 2 C  CH 2 H 3C  N
H 3C  O
: :

H 3C
H

H 3C
C  CH 2
H 3C  O  H 2 C
: :

(P) (Q) (R) (S)

a) P > Q > R > S b) R > Q > P > S c) S > R > Q > P d) Q > R > P > S
Comprehension - II
Hydrocarbon A(C7H12) was treated with BH3; THF; H2O2; NaOH to produce B(C7H14O) as only product
Reaction of ‘B’ with TsCl/ pyridine followed by KOH gives ‘C’ (isomeric with A) in addition to the olefinic
products. Treatment of ‘C’ with ozone follerved by Zn/ACOH produces onlycompound shown below
CHO
CHO

H3C
20. What is correct structure of ‘A’

a) b) c) d)

21. What is correct structure of ‘B”

OH OH
a) b) c) d)
OH

OH

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22. What is the correct structure of comppound ‘C

a) b) c) d)

SECTION - D
Matching Type Questions
23. Column - I Column - II

a) p) homocyclic compound

b) q) Closed chain hydrocarbon

c) r) Bicyclobridge heads are present.

d) s) spiro carbon chain

24. Column - I Column - II

OH  
Con. H 2 SO4
a) 
p) Hoffmanns alkene
Cl
b) 
C2 H 5O / etOH
 q) Saytzeeff’s alkene

c) 
Me3CO K
 r) Transition state
Cl
Br
d) 
alc . KOH
 s) carbocation

SECTION - E
Integer Type Questions
25. How many cycloalkenes on catalytic hydrogenation given methyl cyclohexane
Br
26. A) 
alc . KOH
 (X) products B) 
alc . KOH
 (Y) products
Br

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 C) 
alc . KOH
 (Z) products
Br
Sum of X + Y + Z ( Including stereo isomers)
27. Number of   H in the major product of the reaction
OH


H

product
(major)
28. Number of benzylic hydrogens are present in the given hydrocarbon

OH
H H  

OH  OH   OH 

H H
29. A) 
B) C)
 
D) 

Total number of products obtained in above reaction including minor products is (including stereo isomers)
30. How many alkenes on catalytic hydrogenation give isopentane as a product.

HOME TEST - 1 PRACTICE TEST

ANSWERS
1) b 2) b 3) b 4) b 5) d 6) c 7) b 8) c 9) d 10) b
11) abcd 12) a,b,c13) a,b 14) b,c 15) abcd 16) abc 17) c 18)d
19) b 20) c
21) d 22) a 23) A-PQ; B-PQR;C-PQS;D-PQRS 24) A-QS;B-QR;C-PR;D-PR
25) 4 26) 8 27) 8 28) 5 29) 9 30) 3

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