TUTORIAL 4 ALKYNES

QUESTION 1
Reaction of heptyne with aqueous sulphuric acid containing mercuric sulphate, two products, each
having the molecular formula C7H14O, were obtained in approximately equal amounts.
a) Write the structures of enol intermediates which formed in the reaction.
b) Give the structure of the major and minor final products.

QUESTION 2
Illustrate the structural formula of the following compounds:
a) 3-isopropylhex-5-en-1-yne
b) 1-cyclopentyl-2-hexyne
c) 3-methylpent-4-en-1-yne

QUESTION 3
Starting with 2-pentyne, write the chemical equation for the synthesis of:
a) Pentane
b) 2,2,3,3-tetrabromopentane
c) 2,2-dibromopentane
d) trans-2-pentene
e) cis-2-pentene

QUESTION 4
Predict the products(s) from the reaction of 1-hexyne with each of the following reagents:
a) 1 mole of HBr
b) H2O, H2SO4, HgSO4
c) 2 mole of Br2
d) Excess Cl2

QUESTION 5
Suggest the synthetic sequences for the preparation of 2,3-dibromopent-2-ene, from prop-1-yne.

QUESTION 6
Cl
KOH, 200oC Cl2, CCl4
Compound D Compound E
Cl

a) Predict the chemical structure for compound D and E.

b) Give two (2) uses of acetylene in modern days.
 QUESTION 7
2H2, Pt i) NaNH2, 150 OC
Compound E Compound F
Compound D ii) H2O

Cl2
Compound G

a) Predict the structural formula for compound E, F and G.

b) 3-heptyne can be prepared from compound D. Indicate the reagent and condition required
for this reaction.

QUESTION 8

a) Predict the structural formula for compound A and B.

b) Identify the function of concentrated H2SO4 and HgSO4.

QUESTION 9
Give the IUPAC name for the following compounds:

a)

b)
Cl

QUESTION 10

a) Write the equations and all the reagents needed to prepare 2-pentyne from 1-propyne

b) Outline a synthesis for the following compound by using the indicated starting materials and
any other necessary reagents.

H C C H CH3C(Cl)2CH3