TUTORIAL 3

HYDROCARBONS : ALKANES, ALKENES AND ALKYNES

1. Give the IUPAC name for each of the compounds below:

a. H3C CH2CH2C CH b.
C C
H CH2CH3

c. d H C CCH2CH CH2

2. Write structural formula for the following compounds:

a. Pent-1-en-4yne b. 5-methyl-hex-1-yne

3. 2-bromo-2,3-dimethylbutane undergoes dehydrodehalogenation to form alkenes. Give the

structures for these alkenes. Which is the major product and give your reason.

4. Draw structural formula for all possible isomers for C4H6 (Hint : you can include structures
having double bonds, one triple bond, two rings, one ring and one double bond).
 HgSO4
HC CCH3 + H2O A B
H2SO4
5. Write structures of A and B. Which structure is the major component? What is the term use to
describe the equilibrium between structure A and B?

6. Write and equation for a simple chemical test that would differentiate between the pair of
compounds below:
a. 1-pentyne and 2-pentyne

7. Outline a synthesis of 2-hexyne from acetylene.

8. Arrange the compounds according of increasing boiling points and give reasons
CH3CH2CH2H(CH3)2 CH3(CH2)4CH3 (CH3)2CHCH(CH3)2
9.

KMnO4, -OH-
cold

A H2SO4 H+, H2O C

i) O3
ii) (CH3)2S

D + E

10. Consider the following reaction.

+ HBr F + G

i. Draw structures F and G.

ii. Propose the mechanism for the formation of F and G.
11. Give the reagent and products of A to E.

Cl Zn(Hg)
J K
HCl
AlCl3

KMnO4 HNO3 Br2, UV

N M
P
Hot, concn. H2SO4
SO3H

12. Please complete the reaction below by putting in appropriate structures or reagents.

A
B C

D
13. Propose the mechanism for the reaction below.

HC
C
H C C:Na+ + H3C CH2CH3 H3C CH2CH3

O OH

14. Propose the mechanism of the reaction below:

Bu
H Bu-MgBr H

O ether OH
15. Write the missing reagents and products in the following scheme

NaNH2, liq NH3 CH3CH2Br

HC CH C D

Br2, hv HBr
G F H2C-=CHCH2CH3