EXERCISE-01 CHECK YOUR GRASP

SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)

1. The smallest alkane which can show optical isomerism possesses -
(A) 5 carbons (B) 6 carbons (C) 7 carbons (D) 8 carbons
2. The appropriate reagent for the transformation
O

CH3
is-
HO HO
(A) Zn(Hg)/HCl (B) NH2NH2,OH– (C) H2/Ni (D) NaBH4
3. The relative reactivity of 1ºH, 2ºH and 3ºH in bromination reaction has been found to be
1 : 82 : 1600 respectively. In the reaction -

CH3 CH3 CH3

hv
CH3–CH–CH3 (excess) + Br2 CH3–C–CH3+CH3–CH–CH2–Br
Br
(A) (B)

the percentage yields of the products (A) and (B) are expected to be -
(A) 99.4%, 0.6% (B) 50%, 50% (C) 0.6%, 99.4% (D) 80%,20%
4. The least reactive alkane towards free-radical substitution reactions is-
(A) CH4 (B) (CH3)3CH (C) CH3CH3 (D) CH3CH2CH3
5. For the reaction

HSO
2 4
CHOH
2

the major product is :

(A) CH2 (B) CH3 (C) (D)

6. Propene is allowed to react with B2D6 and the product is treated with acetic acid. The final product obtained
is -
(A) 1–deuteriopropane (B) 2–deuteriopropane
(C) 1–deuteriopropene (D) 2–deuteriopropene
7. 1–Methylcyclohexene is allowed to react with B2H6. The product is then treated with H2O2 and NaOH.
The reaction is -

1.B2H6
–
2.H2O2/OH
CH3

The product formed is

(A) 1–methylcyclohexanol (B) 2–methylcyclohexanol
(C) methylcyclohexane (D) cyclohexanol
8. Propene on reaction with ICl produces mainly -
(A) 1–chloro–2–iodopropene (B) 2–chloro–1–iodopropane
(C) (±)–2–chloro–1–iodopropane (D) (±)–1–chloro–2–iodopropane
9. Consider the reaction
CH3
+ – Heat
CH3CH2CH2–N–CH2CH3 OH
CH3
Which of the following is formed in major amount
(A) CH2=CH2 (B) CH3CH=CH2
(C) Both (A) and (B) in equal amount (D) None, as no reaction takes place
10. In the addition of HBr to propene in the absence of a peroxide, the first step involves the addition of -
(A) H+ (B) Br– (C) H (D) Br 
11. In the reaction
CH3CH2CH=CH 
2 2 1.Hg(OAc) ,H O
2 2.NaBD4

the product obtained is -

(A) CH3CH2CHOHCH2D (B) CH3CH2CHDCH2OH
(C) CH3CH2CD(OH)CH3 (D) CH3CH2CD2CH2OH
12. The major product obtained in the reaction of 1,3-Butadiene with HCl (1 mole) at a higher temperature
(100ºC or above) is
(A) 3,4–dichloro–1–butene (B) 3–chloro–1–butene
(C) 1–chloro–2–butene (D) 2–chloro–2–butene
13. An optically active hydrocarbon (X) on catalytic hydrogenation gives an optically inactive compound (Y),
C6H14. The hydrocarbon (X) is-
(A) 3–methyl–1–pentene (B) 3–methyl–2–pentene
(C) 2–ethyl–1–butene (D) 3–methylcyclopentene
14. The addition of HCl to 1–phenylpropene gives-
(A) C6H5CHClCH2CH3 (B) C6H5CH2CHClCH3
(C) C6H5CH2CH2CH2Cl (D) C6H5CH(CH3)CH2Cl
15. The reduction of 4–octyne with H2 in the presence of Pd/CaCO3 – quinoline gives-
(A) trans–4–octene (B) cis–4–octene
(C) a mixture of cis–and trans–4–octene (D) a completely reduced product C8H18
16. The ease of formation of free radicals follows the order -
 
(A) 3º  2º  1º  C H3 (B) C H3  1º  2º  3º
 
(C) 1º  2º  3º  C H3 (D) 2º  1º  3º  C H3
17. Which of the following has the lowest heat of hydrogenation per mole -
(A) cis–2–Butene (B) trans–2–Butene (C) 1–Butene (D) 1,3–Butadiene
18. The intermediate formed during the addition of HCl to propene in the presence of peroxide is-
   
(A) CH 3 C HCH2 Cl (B) CH 3 CH 2 C H2 (C) CH 3 C HCH3 (D) CH 3 CH2 C H2
19. The order of stability of the alkenes
R2C=CR2, R2C=CHR, R2C=CH2, RCH=CHR, and RCH=CH2
I II III IV V
is -
(A) I > II > III > IV > V (B) I = II > III > IV > V
(C) II > I > IV > III > V (D) V > IV > III > I > II
20. Which of the following will not react with an ammonical silver nitrate solution :
(A) CH3CCH (B) (CH3)2CH–CH (C) CH3CCCH3 (D) HCCH

CHECK YOUR GRASP ANSWER KEY EXERCISE -1

Qu e . 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans . C B A A C B B B A A A C A A B A D C A C
EXERCISE–02 BRAIN TEASERS

SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Which of the following reactions will result in the formation of a chiral centre in the product -
(A) CH3CH=CHCH3+HBr  (B) CH3CH=CH2+HOBr 

(C) CH3CH2CH=CH2+HBr 

H2O2
(D) CH3CH2CH=CH2+HBr 

2. Propene on reaction with N–bromosuccinimide in CCl4 produces -

(A) 1, 2–dibromopropane (B) 3–bromopropene
(C) 1–bromopropene (D) 2–bromopropene
3. cis–2–Butene on reaction with Br2 in CCl4 produces mainly -
(A) 1–bromo–2–butene (B) 2,3–dibromobutane
(C) meso–2,3–dibromobutane (D) (±) 2,3–dibromobutane
4. The bond dissociation energies of the following

CH3–H CH3CH2–H CH2=CH–CH2–H C6H5–H

I II III IV

vary in the order :

(A) I > II > III > IV (B) IV > III > II > I (C) IV > I > II > III (D) II > I > IV > III
5. Which of the following decolourises alkaline KMnO4 solution
(A) C3H8 (B) C2H4 (C) CH4 (D) CCl4
6. Compounds capable of reacting with ammonical AgNO3 solution are

(A) CH3 CH C CH (B) HC CH (C) 1- Butyne (D) all the above

CH3

7. A hydrocarbon which decolourises KMnO4 but does not give any precipitate with ammoniated AgNO3
(A) Benzene (B) Acetylene (C) Butyne (D) 2–Butene
8. Compound 'A' on chlorination gives compound 'B', compound 'B' reacts with alc. KOH gives gas 'C', which
decolourise Baeyer reagent. ozonolysis of compound 'C' gives only HCHO compound. 'A' is :
(A) C2H6 (B) C2H4 (C) C4H10 (D) C2H5Cl

9. Which reagent converts propene to 1–propanol

(A) H2O, H2SO4 (B) B2H6, H2O2, OH–
(C) Hg(OAc)2,NaBH4/H2O (D) Aq. KOH
10. Which one of the following alkenes will react faster with H2 under catalytic hydrogenation conditions :
[R = Alkyl Substituent]

R R R R R R R H
(A) (B) (C) (D)
R R H H R H R H
11. Arrange the following in order of increase/decrease in boiling point.

CH3CH2CH2CH2CH3 (CH3)2CHCH2CH3 (CH3)4C

I II III

(A) I > II > III (B) II > I > III (C) III > I > II (D) III < II < I
12. What are the products obtained upon the ozonolysis of 2-pentene ?
(A) CH3CH2CHO (B) CH3CHO (C) CH3COCH3 (D)CH3COCH2CH3
13. Which of the following can be used for the preparation of propane ?

1.B H 1.Mg / ether

(A) CH3CH=CH2 2 6
2.CH3COOH
 (B) CH3CH2CH2Cl 
2.H2O



NaOH / CaO
Re d P / HI / 150C
(C) CH3CH2CH2I  
 (D) CH3CH2CH2COONa 



14. Which of the following are correct :

1.O3
(A) 
2.Zn,H2O
 OHC–CH2CH2CH2–CHO
H H

O
(B) C6H5C–OOH
CH2Cl2
H H
H H
O

KMnO4 H H
(C) 
cold dilute solution


H H OH OH

O O
KMnO4
(D)   –O—CCH CH CH C—O–
OH – ,heat 2 2 2
H H

15. 2-Bromo-3-phenylpropane can be synthesised by

(A) C6H5CH2CH(OH)CH3+PBr3 
(B) C6H5CH=CHCH3+HBr+ benzoyl peroxide 
(C) C6H5CH2CH2CH3+Br2+ light 
(D) none of these
16. The nitration of propane with concentrated HNO3 gives :

(A) CH3CH2CH2NO2 (B) CH3CHCH3 (C) CH3CH2NO2 (D) CH3NO2

NO2

17. Which of the follwing will react with sodium metal :

(A) Ethyne (B) 1-Butyne (C) 2-Butyne (D) Ethane
 A
18. —CH=CH2 —CH2CH2OH

B
—CHCH3

OH
C —CH2CH3
OH

A, B and C are :
(A) simple hydration
(B) hydroboronation, mercuration-demercuration, hydration
(C) hydration, hydroboronation, mercuration-demercuration
(D) mercuration-demercuration, hydration, hydroboronation

O O

19. C9 H14 

ozonolysis

(A)

Hence A is :

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

Y X
20.
HO OH HO OH

Select X and Y out of :

I : MnO4 /OH– II : HCO3H

(A) X -I, Y- II (B) X -II, Y- I (C) X -I, Y- I (D) X -II, Y- II

BRAIN TEASERS ANSWER KEY EXERCISE -2

Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A, B,D B D C B D D A B B A, D A, B A,BC,D A,BC,D A,B
Qu e. 16 17 18 19 20
An s . A,BC,D A, B B B A
EXERCISE–03 MISCELLANEOUS TYPE QUESTIONS
TRUE OR FALSE :
1. Although acetylene acidic in nature it does not react with NaOH/KOH.
2. Although C—H bond in acetylene has greatest bond energy of all C—H bond, yet it is most acidic.

:
3. :
CH2=CH is less basic than HC C

4. —C  C— has two  bond yet it is less reactive than —C=C— towards electrophilic addition reaction.

5. Partial reduction of alkynes is either syn or anti.

FILL IN THE BLANKS :
1. Out of cis-2 butene and trans-2-butene, ...................... has the lower melting point.
2. A four-carbon alkyne having weakly acidic character is ......................
3. Alkanes undergo ................... reactions whereas alkynes give .............. reaction.
4. ..................... is a versatile method for locating the position of the double bond in an alkene.
5. The valence atomic orbital on carbon in silver acetylide is ................... hybridized.

MATCH THE COLUMN

1. Match the column I with column II.
Column-I Column-II
(A) Wurtz reaction (p) Electrophilic substitution reaction
(B) Hydration of alkenes (q) Free radical substitution
(C) Nitration of alkane (r ) Electrophilic addition reaction
(D ) Reaction of alkene with NBS (s) Nucleophilic substitution

2. Match the column I with column II.

Column-I Column-II

(A)
CH3—CH2—CH2Br (p) HBr

(B)
CH3—CH=CH2 CH3—CHBr—CH3 (q) HBr + peroxide

(C)
CH3—CHBr—CH2Br (r) NBS

(D) (s) Br2, low temp., dark

BrCH2—CH=CH2

3. Match the column I with column II.

Column-I Column-II
(A) Dehydrohalogenation (p) Kolbe reaction
of alkyl halides
(B) Electrolysis of sodium salt (q) Alc. KOH
(C) Ozonolysis (r ) Addition product of ethylene
(D ) Dichloro ethylene (s) Sodalime
(E) Decarboxylation (t) Alkene