CHM3201 KIMIA ORGANIK 1

JABATAN KIMIA, UPM

Tutorial: Alkenes and Alkynes
1.

Draw the structures for the major products of the following dehydration
reactions:
OH
OH

H+

i.

H+

ii.
HO

OH

H+

iii.

H+

iv.

2.

Using chemical equations, explain the mechanism involved in the

hydrohalogenation reaction of 2-pentene.

3.

Show how the following compounds can be prepared from ethane

i. Ethane
iv. 1,2-Ethandiol

4.

ii. Ethanol
iii. Bromoethane
v. 1,2-Dichloroethane

State the major product, starting reagents and/or reaction conditions for the
following reactions:
i. CH3CH=C(CH3)2

iii. CH3CH2CH=CHCH3

v. (CH3)2C=CHCH3

CH3CH2C(CH3)2OH

+ H2SO4

(CH3)2CO

ii.

iv.

+ HCl

+ KMnO4

25oC

CH3CHO

5.

The bromination of 3,3-diphenyl-1-butene resulted in the formation of 2bromo-2,3-diphenylbutane. Show how this reaction occurred.

6.

The reaction of 2-chloropentane in the presence of sodium ethoxide produced

2 alkene products in different percentage yields. Explain the formation of
these products and state which would be the major and minor products.
Stating with propyne, suggest how you would prepare propene and 2-butyne

7.
8.

Three compounds A,B, and C all have the formula C6H10. All three compounds
rapidly decolorizes bromine in CCl4; all three are soluble in cold concentrated

sulfuric acid. Compound A has a much lower pKA value than B or C.

Compounds A and B both yielded hexane when treated with an excess of
hydrogen in the presence of platinum catalyst. Under these conditions, C only
absorbs 1 molar equivalent of hydrogen and gives a product with formula
C6H12. When A is oxidized with hot basic potassium permanganate and the
resulting solution acidified, the only organic product that can be isolated is
CH3(CH2)3COOH. Similar oxidation of B gives only CH3CH2COOH, and
similar treatment of C gives only HOOC(CH2)4COOH. What are the
structures for A, B and C?
9.

Treating (Z)-2-butene with osmium tetraoxide in pyridine followed with an

aqueous solution of sodium hydrogen sulphite yielded a diol which is
optically inactive and not resolvable. Explain by drawing the reaction
involved. What would you expect to get by treating the same reagents with
(E)-2-butene?

10.

Write the structures for the alkene that would produce the following carbonyl
products on treatment with ozone followed by Zn in acetic acid.
i. CH3COCH3 and (CH3)2CHCHO
ii. (CH2)4CO and HCHO

11.

Three structural isomers of an alkene (C8H16) undergoes oxidative cleavage

when reacted with hot, alkaline potassium permanganate to produce the
following products. Draw the probable structures of the 3 isomers.
i. Isomer 1:
ii. Isomer 2:
iii. Isomer 3:

2 carboxylic acids (3C and 5C)

carboxylic acid (3C) and ketone (5C and optically inactive)
carboxylic acid (2C) and ketone (6C and optically active)

GOOD LUCK