OBJECTIVES

1. When cyclohexane is poured on water, it floats because

(a) cyclohexane is in boat form (b) cyclohexane is in chair form
(c) cyclohexane is in crown form (d) cyclohexane is less dense than water

2. Which order is correct for the decreasing reactivity to ring monobromination of the following compounds?
C6H5CH3 (I), C6H5COOH (II), C6H6 (III), C6H5NO2 (IV)
(a) I > II > III > IV (b) I > III > II > IV (c) II > III > IV > I (d) None of these

3. Which xylene gives only one monobromo derivative ?

(a) Ortho (b) Para (c) Meta (d) None of these

4. The reaction of CH3CH = CH OH with HBr gives

(a) CH3CHBr CH2 OH (b) CH3CH2CH Br OH

(c) CH3CHBr CH2 Br (d) CH3CH2CH Br Br

5. The lowest b.p. is expected for

(a) iso-Octane (b) n-Octane
(c) 2, 2, 3, 3-tetra-Methylbutane (d) n-Butane

6. Reaction of Br2 on ethylene in presence of NaCl gives

(a) BrCH2 CH2Br (b) ClCH2 CH2Br
(c) Both of these (d) None of these

7. The reaction conditions leading to the best yield of C2H5Cl are

UV dark
(a) C2H6 (excess) + Cl2 light (b) C2H6 + Cl2 room temp.

UV UV
(c) C2H6 + Cl2 (excess) light (d) C2H6 + Cl2 light

8. When nitrobenzene is treated with Br 2 in the presence of FeBr 3, the major product formed is
m-bromonitrobenzene. Statements which are related to obtain the m-isomer are
(a) The electron density on meta carbon is more than that on ortho and para positions
(b) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least
destabilished
(c) Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
(d) Easier loss of H+ to regain aromaticity from the meta position than from ortho and para positions

- 73 -
 74 The Hydrocarbons

9. Toluene, when treated with Br2/Fe, gives p-bromotoluene as the major product because CH3 group
(a) is para directing (b) is meta directing
(c) activates the ring by hyperconjugation (d) deactivates the ring

10. Dipole moment is shown by

(a) 1, 4-dichlorobenzene (b) cis-1, 2-dichloroethene
(c) trans-1, 2-dichloroethene (d) trans-1, 2-dichloro-2-pentene

11. Which of the following acid can be used as catalyst in Friedel-Craft reaction ?
(a) AICl3 (b) BF3 (c) HCl (d) HNO3

12. Isomers which can be interconverted through rotation around a single bond are
(a) Conformers (b) Diastereomers (c) Enantiomers (d) Positional isomers

13. The compound having both sp and sp2 hybridised carbon atoms is
(a) Propene (b) Propyne
(c) Propadiene (d) None of these

14. Amongst the following, the compound that is nitrated with difficulty is
(a) Benzene (b) Nitrobenzene (c) Toluene (d) Phenol

15. Amongst the following groups, the group that deactivates the benzene ring for electrophilic substitution
is
.. H ..
(a) CH3 (b) N (c) .O
. H (d) NH C R
H
O
16. Which of the CC bond is strongest ?
(a) Formed by sp3sp3 hybridised carbon atoms (as in alkanes)
(b) Formed by sp2sp2 hybridised carbon atoms (as in alkenes)
(c) Formed by spsp hybridised carbon atoms (as in alkynes)
(d) None of these

17. The CH bond length is longest in

(a) C2H2 (b) C2H4 (c) C2H6 (d) C2H2Br 2

18. Benzene can undergo

(a) Substitution (b) Addition (c) Elimination (d) Oxidation

19. Acetylene is
(a) Red coloured gas (b) Garlic in odour
(c) Soluble in acetone (d) Useful in polymer industry

ABHISHEK TUTORIALS
The Hydrocarbons 75

20. The molecules that will have dipole moment are

(a) 2, 2-dimethylpropane (b) trans- 2-pentene
(c) cis-3-hexene (d) 2, 2, 3, 3 -tetramethylbutane

CCl3
AICl3
21. + Cl2 Z . Z may be

CCl3 CCl3 CCl3

Cl
(a) (b) (c) (d) none of these
Cl
Cl
600C
22. Z . Z may be

(a) (b) (c) (d) None of these

23. + Na Me Z.Z
Z. Z is

Me Na
(a) (b) (c) both (a) and (b) (d) None of these

OH
Br2
24. Z. Z may be
[FeBr3]
COOH
OH OH
Br

(a) COOH (b) COOH

Br
OH

(c) (d) None of these

Br COOH

25. Which represents acidic nature of aniline

NH2 NH2 NH Cl
K
NHK HOCl
(a) H2 (b)

NH2 NH3Cl
(c) + HCl (d) All of these

ABHISHEK TUTORIALS
 76 The Hydrocarbons

OD
D2O
26. + D2SO4 Z. Z may be

OD OD OD
OD
D D D D D
(a) (b) (c) or (d) none of these
D D
D D
D

Me
Br2
27. Me C Me [AlBr3] Z. Z may be

Br Me
(a) (b) C = CH (c) both (a) and (b) (d) none of these
Me

28. How many structures are possible for Phene

(a) 4 (b) 5 (c) 6 (d) 7

29. Which one is an aromatic compound

(a) (b) (c) (d) None of these

30. Which statement is correct about the cylcopropenyl carbonium ?

(a) it is non-aromatic (b) it is aromatic (c) it obeys Huckles rule (d) both (b) and (c)

Cl2H2O
31. CH3CH = CH2 Z. Z may be
Cl
(a) CH3 CH CH2 (b) CH3 CH CH2 (c) CH3 CH CH2 (d) CH3 CH CH2
Cl Cl Cl Cl OH OH Cl

HCOOOH
32. (Peroxyformic acid) Z. Z may be

OH OH H H H H
(a) (b) (c) (d) None of these
H H OH OH O

HIO4
33. CH3 CH C CH3 + [O] Z. Z may be
OH O

(a) CH3 CHO (b) CH3 COOH (c) CH3 C C CH3 (d) None of these
O O

ABHISHEK TUTORIALS
The Hydrocarbons 77

C6 H5 COOOH
34. + [O] Peroxy acid
Z. Z may be

O O
(a) (b) O (c) (d) all of these
O

35. CH2 = CH CH = CH2 + Br2 low temp. Z . Z may be

Br Br
(a) CH2 CH CH = CH2 (b) CH2 CH = CH CH2
Br Br
Br Br Br
(c) CH2 CH CH CH2 (d) CH2 CH = CH CH2
Br Br Br

36. Which one is highly unstable ?

(a) CH2 = CH OH (b) CH2 = CH Cl (c) CH2 = CH CH2 Cl (d) CH3 C CH

OH OH OH
NO2
37. Arrange and in decreasing acidic character..
NO2
NO2

(I) (II) (III)

(a) I > II > III (b) III > I > II (c) I > II > III (d) III > II > I

38. How many functional isomers are possible for tetrose ?

(a) two (b) four (c) six (d) none of these

39. The reaction of 1,3-Butadiene and acetylene gives

(a) (b) (c) (d) None of these

40. Which one of the following heptanols can be dehydrated to hept-3-ene only?
(a) Heptan-3-ol (b) Heptan-4-ol (c) Heptan-2-ol (d) Heptan-1-ol

ABHISHEK TUTORIALS
 MISCELLANEOUS ASSIGNMENT
Comprehension-1

The functional group in alkenes is C-C double bond which is made of one -bond and one -bond.
The weaker -bond would tend to attract the electrophile and convert itself to a stable carbonium
ion which reacts with nucleophile remainder to form the addition product. The addition reaction of
alkenes is stereo specific as well as stereoselective. i.e., the isomeric alkenes react differently with
same addendum to give stereochemically different products. Where addition of HBr proceeds through
carbocation formation and hence racemisation is expected. With low concentration of Br2 in vapour
phase substitution predominates over addition.

1. Reaction of 1,2-dimethylcyclohexene with promine water gives the product

(a) Br CH3 (b) Br Br (c) Br OH (d) Br CH3

CH3 Br CH3 CH3 CH3 CH3 CH3 OH

Br2 /low conc .

2. 14
CH3 CH=CH2
high temperatur e

Product of the above reaction is

(a) Br14 CH 2CH=CH2 (b) 14
CH2 =CHCH2 Br
(c) both (a) & (b) (d) none of these

OH
CH CH CH3 CHCH2CH3

3. H2O/H+

The stereochemistry of product is

(a) dextro (b) laevo (c) meso (d) racemic

4. Trans-2-butene when reacts with Br2, the product formed is

(a) racemic mixture (b) mesoform
(c) optically pure (d) no specific stereochemistry

Comprehension-2

For selective bromination of organic compounds, N-Bromosuccinimide is used for reaction system
alkenes as well as arenes that have alkyl groups on the ring react with NBS in the presence of light or
benzoylperoxide to give compounds which are bromo substituted at the -position to the double bond or
benzene ring

- 78 -
The Hydrocarbons 79

CH3 CH2 Br

e.g., NBS, CCl4

(C6H5COO)2

5. As given in the passage whenever allylic halogenations are performed direct use of Br2 or Cl2 is not
done. This is because
(a) for allylic halogenation high concentration of halogen is required
(b) for allylic halogenation low concentration of halogen is required
(c) NBS is highly specific
(d) direct use of halogen requires high energy for breakage

6. Which of the following will react most readily with NBS to give the allylic substituted product?
(a) CH2=CHCH2 CH3 (b) CHCCH2 CH3

O
CH2 CH CH2
C O CH2 CH CH2
(c) (d)

7. From which of the following generation of Br radical takes place when reaction is
NBS, CCl4
CH2 =CHCH3 (C6H5COO) 2
CH2 =CHCH2Br?

O O

(a) N Br + HBr N H + B r2

O O

Br
+ Br Br + Br

O O

N Br N + Br
(b)
O O

O O O
C O O C C O
(c)

O
C O
+ CO2

ABHISHEK TUTORIALS
 80 The Hydrocarbons

O O

+ N Br N + Br

O O
(d) Br radical is not produced during the reaction

Comprehension-3

n-Butane is produced by mono bromination of ethane followed by Wurtz reaction, as follows

Br2
(i) CH3CH3 hv CH3CH2Br

(ii) CH3CH2Br Na CH3CH2CH2CH3 + CH2=CH2 + CH3CH3 + NaBr

Mechanism
Na Na+ + e; CH3CH2Na + CH3CH2Br CH3CH2CH2CH3 + CH2=CH2 + CH3CH3

CH3CH2Br CH3 CH 2 B r

CH3 CH 2 + e CH3CH2

8. The amount of ethyl bromide required to prepare 55g of butane would be

(a) 106.72 (b) 206.72 (c) 20.67 (d) 2.067

9. If the yield of n-butane was 85%, then the actual amount of ethyl required to produce 55g of n-butane
would be
(a) 2.432 g (b) 24.32 g (c) 243.2 g (d) 0.2432 g

10. The other products which could be formed

(a) CH2=CH2 (b) CH3 CH 2 CH 3
(c) CH 4 (d) CH3 CH 2 CH 2CH 2CH 3

Each of the questions given below consists of two statements, an assertion (A) and reason (R).
Select the number corresponding to the appropriate alternative as follows
(a) If both A and R are true and R is the correct explanation of A.
(b) If both A and R are true but R is not the correct explanation of A.
(c) If A is true but R is false.
(d) If A is false but R is true.

11. A: In , unsaturated compounds with C=C, and C=O conjugated, attack of nucleophile takes place
on C=C.
R: The C=O bond is stronger than C=C.

12. A: Alkyl iodides are more reactive than alkyl chlorides for elimination reactions.
R: I is a better leaving group than Cl.

ABHISHEK TUTORIALS
The Hydrocarbons 81

13. A: CH3CH2 is a stronger base than F.

R: The negative charge density on carbon is greater than the negative charge density on F.

14. A: CH3CCCH3 is more reactive than CHCH towards HCl.

R: The carbocation formed is more stable in the case of CH3CCCH3 than CHCH.

15. A: CHCH reacts with HCl in the presence of HgCl2 while CH2=CH2 does not.
R: There is more unsaturation in CHCH than in CH2=CH2.

ABHISHEK TUTORIALS
 BASIC PROBLEMS

1. Compound (X) (C5 H8O) does not appreciably react with Lucas reagent at room temperature but gives
a precipitate with silver nitrate (amonioacal). With Me Mg Br, 0.42 gms of (X) gives 22400 ml of CH4 at
STP. Treatment of H2 in the presence of Pt catalyst followed by boiling with excess HI, gives
n-pentane. Suggest the structure for (X) and write equations involved.

2. The freezing point constant of C6H6 is 4.90 and its melting point 5.51C. A solution of 0.810 g of
a compound (A) when dissolved in 7.5 gms of benzene freezes at 1.59C. The compound (A) has
C = 70.58%. Compound (A) on heating with sodalime gives another compound (B) which on oxidation
and subsequent acidifications gives an acid (C) of equivalent weight 122. (C) on heating with sodalime
gives benzene. Identify (A), (B) and (C) and explain the reactions involved.

3. When bromo benzene is mono chlorinated, two isomeric compounds (A) and (B) are obtained.
Monobromination of (A) gives several isomeric products of formula C6H3Cl Br2. While mono bromination
of (B) yields only two isomeric (C) and (D). Compound (C) is identical with one of the compound
obtained from the bromination of (A). However (D) is totally different from any of the isomeric compounds
obtained from bromination of (A). Give structures of (A), (B) and (D) with explanation.

4. Compound (A) C5H10 decolourizes Br2. When (A) is treated with hot KMnO4, two acids (B) and (C)
are formed. When (B) is treated with soda lime, methane is formed. When (C) is heated with soda lime
ethane is formed. What are the structure of (A), (B) and (C).

5. An organic compound (A) C6H12 is treated with Cl2 in the presence of CCl4 gives (B) C6H12Cl2. Compound
(B) on treatment with alcoholic KOH followed by NaNH2 resulting in the formation of compound (C) C6
H10. compound (C) on treatment with H2 (gas) over platinum forms 2-methyl pentane. Compound (C)
gives ammoniacal AgNO3 test. Ozonalysis of (A) gives two aldehydes (D) and (E) where E is
acetaldehyde. Identify A, B, C, D and E.

6. The compounds (A) and (B) have same molecular formula C4 H6 gave the following reactions
(i) Both discharge colour of Br2 in CCl4
(ii) (A) gives a precipitate with ammoniacal AgNO3 and on oxidations gave propanoic acid and CO2.
(iii) (B) does not give white precipitate with ammoniacal AgNO3 and on oxidations gave oxalic acid
and CO2 what are (A) and (B)

7. A hydrocarbon (A) is treated with excess of HCl. A dihalogen derivative (B) is formed. Compound
(B) on treatment with aqueous KOH gives C. Compound (C) can be obtained by heating calcium salt
of 2-methyl propanoic acid with calcium acetate what are A, B and C ?
8. An organic compound (A) C9H12 gave (B) C8H6O4 on oxidation by alkaline KMnO4. (B) on heating
does not form anhydride. Also (B) reacts with Br2 in the presence of iron to give only one monobromo
derivative (C). C8H5BrO4. What are A, B and C.

9. A hydrocarbon (A) C9 H10 adds Cl2 to give (B) C9H10Cl2. Hydrolysis of (B) gives (C) C9H12O2. Oxidation
of (A) gave two acids identified as benzoic acid and acetic acids. What are A, B, and C ?

- 82 -
The Hydrocarbons 83

10. An organic compound (A) C9H10 Br2 forms C9 H11 OBr with caustic soda solution the later is resistant
to further action of alkali. (B) on treating with H2SO4 converts into (C) which on ozonalysis gives ethanal
and another compound (D). Identify (A) to (D) and give reactions.

11. An aromatic hydrocarbon (A) (mol. wt. = 92) containing C = 91.3% and H = 8.7% gave on treatment
with chlorine three isomeric compounds (B), (C) and (D) each containing 28% chlorine. On oxidation,
each of three gave monobasic acids X, Y and Z respectively. The acid (X) can also be obtained by the
oxidation of (A) while (Y) and (Z) contained chlorine also. The acid X on reaction with soda lime gave
benzene while acids (Y) and (Z) on similar treatment gave chlorobenzene. What are A, B, C, D, X, Y, Z.

12. An organic compound (A) C6H10, on reduction first gives (B) C6H12 and finally (C) C6H14. (A) on
ozonolysis followed by hydrolysis gives two aldehydes (D) C2H4 O and (E), C2H2O2. Oxidation of (B)
with KMnO4 gives the acid (F) C4H8O2. Determine the structures of (A) to (F) with proper reasoning.

13. An organic compound (A) of molecular formula C5H8 when treated with Na in liquid ammonia followed
by reaction with n-Propyl iodide yields (B) C8H14. (A) gives a ketone C5H10O when treated with dil.
H2SO4 and HgSO4. (B) on oxidation with alkaline. KMnO4 gives two isomeric acids (D) and (E) C4H8O2.
Give structures of compounds (A) to (D) with proper reasoning.

14. An organic compound (A) C8H6, on treatment with dil. H2SO4 containing mercuric sulphate gives a
compound (B), which can also be obtained from a reaction of benzene with acid chloride in the presence
of anhydrous AlCl3. The compound (B) when treated with iodine in aq. KOH, yields C and a yellow
compound (D). Identify A, B, C and D with justification.

15. An organic compound A(C5H8) on hydrogenation gives compound B(C5H12). Compound A on ozonolysis
gives formaldehyde and 2-ketopropanal. Deduce structure of compound A.

16. A hydrocarbon (P) of the formula C8H10, on ozonolysis, gives compound Q (C4H6O2) only. The compound
(Q) can also be obtained from an alkyl bromide, R (C3H5Br) upon treatment with Mg in dry ether,
followed by CO2 and acidification. Identify (P), (Q) and (R) and give equations for the reactions.

17. Synthesize meso-3,4-dibromohexane from CH CH.

18. Two isomeric alkyl bromides (A) and (B) have molecular formula C5H11Br. (A) on treatment with
alcoholic KOH gives two isomers (C) and (D) of formula C5H10. (C) on ozonolysis gives fromaldehyde
and 2-methylpropanal. (B) with alcoholic KOH gives (D) and (E). Catalytic hydrogenation of (C), (D)
and (E) gives (F) C5H12. Identify (A) to (F).

19. A compound (A) has C = 85.7%, H = 14.3%. Its molecular weight is 70. It does not react with Cl2 in
dark but gave a substitution product C5H9Cl in presence of light. What is (A) ?

20. An organic compound (A) C6H10 does not react with ammoniacal AgNO3 but on reduction first gives
(B) C6H12 and then (C) C6H14. (A) on ozonolysis gives two aldehydes C2H4O (D) and C2H2O2 (E).
Oxidation of (B) with alkaline KMnO4 gives acid (F) C3H6O2. What are (A) to (F) ?

21. Two isomeric organic compounds (A) and (B) on reduction with ZnCu couple give n-butane. On
treating (A) and (B) with Na and ether separately, n-octane (C) and 3, 4-diemthylhexane (D) are formed
but if a mixture of (A) and (B) reacts with Na and ether, one more product (E) in addition to (C) and (D)
is formed. What are (A) to (E) ?

ABHISHEK TUTORIALS
 ADVANCED PROBLEMS

Br
C2H5 Cu poweder (A)
1.

write the structure of A and explain its stereochemistry

AlCl3 Zn Hg Br2 / Fe
2. + CH3COCl A HCl
B
C
NO2

AlBr3
3. CF3CH = CH2 + HBr X

Me
4. Nitration of With HNO3 in acetic acid solvent at 45C occures 25 times faster than nitration of

under same condition and the percentage are ortho = 56.5 meta = 3.5 and para 40.0. What is the

partial rate factor. Can these values be taken for other electrophilic substitution reactions of toluene

5. The values for nitration of t butyl benzene are o = 4.5, m 3.0 p = 75. How much more reactive is
t-butyl benzene than benzene.
6. Which of the following C6H6 structure gives only one C6H5Br isomer

CH2
CH2

CH2 CH2
(b) (c) (d)
(a)

CH2
7. What are the possible products from 1, 4- addition of HBr on . Draw all possible carbocations

and state which carbocation is more stable.

8. + CH2 = CH CH = CH2 A. Predict the structure of A and explain.

H H
9. How would you bring about the following conversion
(i) 1, 3 - Butadiene to racemic -1, 4 - dibromo 2, 3- dideutrobutene

(ii)

- 84 -
The Hydrocarbons 85

Me H
NBS (i) Li
(iii) H
CC A B
Me (ii) Cu P
(iv) Z-2, 3- Dideutero -2- butene to (iii) A
racemic-erythro-2-
Bromo-2, 3- Didenterobutane
(v) 1-Methyl cyclopentene to trans -2- Methyl cyclopentane

O C
(vi) C Me to (S, S) Glycol + R, S Glycol
H
Me

10. Arrange the following free radials in order of increasing stability and explain your order.
. . .
CH3CH CH(CH3)2, CH2CH2 CH(CH3 )2 and CH3CH2, C(CH 3)2

11. The relative reactivity primary, secondary and tertiary hydrogens to chloroiation is 1 : 3.8 : 5
(i) Calculate the amounts of all the monochlorobutanes obtained from the reaction of butane with
chlorine.
(ii) Calculate the amounts of all the monochlorobutanes when isobutane is treated with chlorine.

12. An alkane C6H14 is found to give only two isomers of monochloro alkanes on chlorination. What is the
structure of C6H14.

13. Draw structures of all possible isomers of C4H6.

14. Find out the degree of unsaturation in the case of C3H3Cl3, C3H4O and C4H5.N

15. Assign E/Z configuration to each of the following alkenes.

BrCH2 CH3
H3 C CH2CH3
C=C C=C
(a) (b)
H H H3C CH2CH3

Br CH(CH3)2 H CH2Cl
C=C C=C
(c) (d)
HOCH2 CH2CH2CH3 H3CCH2 COOH

16. Can we isolate the following compounds ? Explain

(a) H (b) (c)

H

ABHISHEK TUTORIALS
 86 The Hydrocarbons

17. Give all major and minor products which will be obtained on acid-catalyzed dehydration.
CH3 OH

(a) CH3CH2CH(OH)CH2CH3 (b)

CH2OH

(c) (CH3)3C.CH2OH (d)

CH2OH

(e)

18. Predict the product of the reaction between (CH3)2C= CH2 and 1Cl.

19. Identify the product of the reaction of isobutylene with H2S in conc. H2SO4. Why does reaction fails
in the absence of conc. H2SO4

20. Compare the regioselectivity of the reaction of HBr with

(a) CF3CH = CH2 (b) Br.CH = CH2 and (c) CH3OCH = CH
CH3

21. Give the stereochemical structure of the reaction product of Br2 with (i) Cis2butene and (ii) trans
2butene. In terms of its stereochemistry characterise this type of reaction.

22. Give the product with the stereochemistry of the reaction of cyclohexene with (i) Br2 (ii) Br2 in the
presence of NaCl and (iii) Br2 in CH3OH.

ABHISHEK TUTORIALS
 ANSWERS

Objectives
1. (d) 2. (d) 3. (b) 4. (b)
5. (d) 6. (c) 7. (a) 8. (a,b)
9. (a,c) 10. (b) 11. (a,b) 12. (a)
13. (c) 14. (b) 15. (d) 16. (c)
17. (c) 18. (a,b) 19. (c) 20. (c)
21. (c) 22. (a) 23. (b) 24. (a)
25. (a) 26. (a) 27. (d) 28. (a)
29. (d) 30. (d) 31. (d) 32. (c)
33. (a,b) 34. (d) 35. (a) 36. (a)
37. (b) 38. (a) 39. (b) 40. (b)

Miscellaneous Assignment
1. (d) 2. (c) 3. (d) 4. (b) 5. (b)

6. (c) 7. (a) 8. (b) 9. (c) 10. (a)

11. (c) 12. (a) 13. (a) 14. (a) 15. (b)

Basic Problems

1. CH2 CH2CH2 C CH
OH

CH3 COOH

2. A = C6H5(CH3)COOH, B= C= D=

Br Br Br
Br
Cl
Br
Br
3. Cl Cl Cl
(A) (B) (C) (D)

4. CH3 CH2 CH CH CH3, CH3 COOH

(A) (B)
CH3 CH2 COOH (C)

- 87 -
 88 The Hydrocarbons

5. CH3 CH CH (CH3)2 CH3 CH (Cl) CH (Cl) CH (CH3)2

(A) (B)
CH3 C C CH (CH3)2 (CH3)2 CH CHO
(C) (D)

6. (A) = CH3 CH2 CCH (B) = CH2 CH CH = CH2

7. (A) = (CH3)2 CH CCH (B) = (CH3)2 CH C (Cl)2 CH3 (C) = (CH3)2 CH CO CH3

CH3 COOH COOH

8. (A) C6 H4 (B) C6 H4 (B) C6 H3 Br
C2H5 COOH
COOH
CH = CH CH3 CH(Cl) CH (Cl)CH3 CH(OH) CH (OH)CH3
9. (A) (B) (C)

Br OH
CH = CH CH3 CHO
CH CH2 CH3 CH CH2 CH3

10. (A) (B) (C) (D)

Br Br
Br Br

CH3
Me CH2Cl Me
Cl
11. A= B= C= D=
Cl
COOH
COOH COOH
Cl
X= Y= Z=
Cl
12. A = CH3 CH = CH CH = CH CH3
B = CH3 CH2 CH2 CH = CH CH3
C = CH3 CH2 CH2 CH2 CH2 CH3
D = CH3 CHO
E = CHO CHO
F = CH3CH2CH2COOH

CH3
13. A = CH3 CH C CH

CH3

B = CH3 CH C CH2 CH2 CH3

CH3

C = CH3 CH C CH3
O
D = CH3CH2CH2COOH
E = CH3 CH CH3
COOH

ABHISHEK TUTORIALS
The Hydrocarbons 89

14. A = C6H5 C CH B = C6H5 C CH3

O
C = C6H5COOH D = CHI3

CH3
15. A = CH2 = C CH = CH2

B = CH3 CH CH2 CH3

CH3

16. P= CC

Q= COOH

R= Br

18. (A) = CH3 CHBrCH (CH3)2 , (B) = CH3 CH2CBr (CH3)2 , (C) = CH2 = CHCH (CH3)2 ,
(D) = CH3 CH=C(CH3)2 , (E) = CH3 CH2 C=CH2 , (F) = CH3 CH2CH (CH3)2 ,
CH3

19. CH2 CH2

CH2 CH2

CH2

20. (A) = CH3 CH = CH CH= CH CH3 ,

(B) = CH3 CH2 CH2 CH= CH CH3

(D) = CH3 CHO, (E) CHO CHO, (F) CH3 CH2 ,COOH

21. (A) = CH3 CH2 CH2 CH2 Cl, (B) CH3CHClCH2CH3 , (C) octane,

(D) = CH3 CH2 CHCH CH2 CH3 ,

CH3 CH3
CH2CH3
(E) = CH3 CH2 CH2 CH2 CH
CH3

Advanced Problems

1.
Et Et

Br
COCH3 C2H5
2. A= B= C= C2H5

3. CF 3CH2CH2Br

ABHISHEK TUTORIALS
 90 The Hydrocarbons

6. Only (a) and (b)

8.
H
. . .
10. CH2 CH2 CH(CH3)2 < CH3 CH CH(CH3)2 < CH3 CH2 C(CH3)2

11. (i) 1-chloro butane = 31.25% (ii) Isobutyl chloride = 70.31%

2-chloro butane = 68.75% 2-Methyl-2-chloro butane = 29.68%

12. CH3 CH CH CH3

CH3 CH3

Me Et H Et
17. (a) C=C + C=C (b)
H H Me H
Me

Me H
(c) Me C = C (d)
Me
Me

(e)

CH3
19. CH3 C SH
CH3

20. (a) CF3CH2 CH2 Br (b) CH3 CH Br

Br
OCH3
(c) CH3 CH2 CH Br

21. cis-2-butene gives a racemic mixture of 2, 3-dibromobutane

trans-2-butene gives a meso form of 2,3-Dibromo butane

22. (i) Br H (ii) Br H + Br H

H Br H Br H Cl

(iii) Br H + Br H

H Br H OMe

ABHISHEK TUTORIALS