CHAPTER PRACTICE PROBLEMS CHEMISTRY

Alkynes
Name : ______________________________________ Batch : Date :

1. 0.34 g of hydrocarbon when heated with methyl magnesium bromide gives 112 ml of CH 4 at STP. Give the
possible structures of the hydrocarbon.
Ans: Terminal alkyne having molecular formula C5H8

2. A certain hydrocarbon A was found to contain 85.7 percent carbon and 14.3% hydrogen. This compound
consumes 1 mole equivalent of hydrogen to give a saturated hydrocarbon B. 1.0 g of hydrocarbon (A) just
decolorized 38.05 g of a 5 percent solution (by mass) of Br2 in CCl4. Compound A, on oxidation with
concentrated KMnO4, give compound C(C4H8O) and compound C could easily be prepared by the action of
acidic aqueous mercuric sulphate on 2-Butyne. Determine the molecular formula of A and deduce the
structure of A, B and C.
Ans: Molecular formula of A is C6H12
(A) H 3C
C CH CH3
H2C-H3C
(B) H3C CH2 CH CH2 CH3
CH3
(C) H3C C CH2 CH3

O
3. An unsaturated hydrocarbon A (C6H10) readily gives (B) on treatment with NaNH2 in liquid NH3. What (B) is
allowed to reach with 1-chloropropane a compound (C) is obtained. On partial hydrogenation in the presence
of Lindlars catalyst, compound (C) gives (D) (C 9H18). On ozonolysis, (D) gives 2, 2-Dimethyl propanal
and 1-butanal. Give the structure of (A), (B), (C) and (D) with proper reasoning.

Ans:

3. (A) (B) +
Na

(C) (D)

4. Compound A with molar mass 108 gmol-1 contained 88.89% C and 11.11%H. It gave a white precipitate with
ammonical silver nitrate. Complete hydrogenation of A gave another compound B with molar mass
112 g mol-1. Oxidation of A gave an acid with equivalent mass 128g/eq. Decarboxylation of this acid gave
cyclohexane. Give structures of A and B and write the reactions involved.

Ans:

(A) C CH (B) CH2CH3

 CHAPTER PRACTICE PROBLEMS CHEMISTRY
5. Compound A (C6H12) is treated with Br2 to form compound B (C6H12Br2). On treating B with alcoholic KOH
followed by NaNH2, the compound C (C6H10) is formed. C on treating with H2/Pt forms 2-methylpentane. The
compound C does not react with ammonical Cu2Cl2 or AgNO3. When (A) is treated with cold KMnO4 solution,
a diol D is formed which gives two acids E and F when heated with KMnO 4 solution, Compound (E) is found
to be ethanoic acid. Deduce the structures from A to F.

Ans:

(A) H3C CH CH CH(CH3)2 (B) H 3C CH CH CH CH3

Br Br Me

(C) H3C C C CH(CH 3)2 (D) H3C CH CH CH(CH 3)2

OH OH

(E) CH3 COOH (F) H3C HC COOH

CH 3

6. Explain the following.

(A) Why alkenes are more reactive than alkanes?
(B) Acetylene reacts with ammonical silver nitrate while ethylene does not.
(C) but-2-ene shows geometrical isomerism but but-1-ene does not show.
(D) Why alkynes are slightly more soluble in water than alkenes and alkanes?

7. An isomer of butyl bromide (C4H9Br) (A) forms an alkene, C4H8 (B) with alcoholic KOH. (B) reacts with
bromine to give another compound (C) with molecular formula C 4H8Br2, which when treated with KNH 2
produces a gaseous compound (D), C4H6. Compound (D) forms a red precipitate when passed through
ammonical Cu2Cl2. Give the structure of compounds (A), (B), (C) and (D)

Ans:

(A) CH3 CH2CH2CH2Br (B) CH3 CH2 CH CH2

(C) CH3 CH2CHBrCH2Br (D) CH3 CH2C CH

8. An organic compound (A) with molecular formula C5H8 when treated with sodium in liquid NH3 followed by
treatment with n-propyliodide yields C8H18 (B). When treated with dil H2SO4 containing mercuric sulphate, (A)
gives the Ketone, C5H10O (C). On oxidation with alkaline KMnO4, (B) gives two isomeric acid C4H8O2 (D and
E). Identify the compounds (A) to (E).

Ans:
(A) H3C CH C CH (B) H3 C CH C C CH 2 CH 2 CH3
H3C H3 C
O
(C) H3C CH C CH3 (D) CH3 CH2 CH2 COOH

H3C
CH 3
(E) H3C CH COOH
 CHAPTER PRACTICE PROBLEMS CHEMISTRY
9. Identify (x), (y) and (z) in the following synthetic schene and write their structures.
(i) NaNH2 H2/Pd - BaSO4 alkaline KMnO4
CH2CH3C CH (X) (Y) (Z)
(ii) CH3CH2Br
Is the compound (Z) optically active? Justify your answer.

Ans: CH3 CH2 C C C2H5 (X)

NO

10. How will you prepare the following compounds from acetylene?
(A) Acetaldehyde (B) Benzene (C) Ethyl alcohol (D) Ethylene
(E) Acetic acid (F) Acetone

11. Show reagents and experimental conditions you might use to convert each starting material in the
desired product. Some of these can be done in one step. Others can be done in more than one step.
CH3CH2CH2 H
(A) CH3CH2CH2C CCH3 C C
H CH3

CH3CH2CH2 CH3
C C
H H

(B) CH3 (CH2)4 C CH CH3(CH2)4 C C Na
(C) CH3 (CH2)4 C CH CH3CH2 C CD
12. Acidic hydrogen is present in
(A) Ethyne (B) Ethene (C) Benzene (D) Pentene

13. A compound X(C5H8) reacts with ammonical AgNO3 to give a white precipitate, and on oxidation with
hot alkaline KMnO4 gives the acid, (CH3)2CHCOOH. Therefore, X is
(A) CH2 = CHCH = CHCH3 (B) CH3 (CH2)2C CH
(C) (CH3)2CHC CH (D) (CH3)2C = C = CH2

14. Among the following compounds, the strongest acid is

(A) HC CH (B) C4H6 (C) C2H6 (D) CH3OH

15. Butyne 1 and Butane 1 can be distinguished by

(A) conc. H2SO4 (B) Br2 in CCl4
(C) dil. H2SO4 (D) AgNO3 in Ammonia