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Monochlorination of butane gives two constitutional isomers: 1-chlorobutane and 2-chlorobutane. Dichlorination of butane yields six constitutional...

Monochlorination of butane gives two constitutional isomers: 1-chlorobutane and 2-chlorobutane. Dichlorination of butane yields six constitutional isomers. Four of these six isomers are drawn below. Draw the structures of the two missing isomers.


Monochlorination of butane gives two constitutiona


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Concepts and reason

Halogenation:

Halogenation is an organic reaction which involves the addition of one or more halogens to a compound.

Halogens in the presence of heat or light react with alkanes to give alkyl halides. The general scheme for halogenation under light or hv is given below:

X2
HCR
X-
C-
R
hv/light
H
where X is any dihalide except F2

In organic chemistry, the relationship between a pair of compounds can be explained by isomerism.

Fundamentals

Radical halogenation of alkanes:

The substitution of a halogen that takes place by replacing the hydrogen atom in the alkane in the free radical pathway is represented as radical halogenation. According to the type of reactant, the single product or multiple products can be determined.

Example of monohalogenation of propane:

Η
Η
Η
Η-
-Η
–
X
+
H-
hy
Η
Η
Η
Η
Η
Η
Η
Η
Η

Example of di-halogenation of propane:

Two types of di-halogen substitution can take place.

1.The two halogen atoms can replace any two hydrogen atoms attached to any two different carbon atoms.

Η
Η
Η
Η-
–
Η
+
-Η
I
Η-
-Η
hv
Η
Η
Η
Η
Η
Η
Η
Η
Η

2.Or the two halogen atoms can replace any two hydrogen atoms attached to the same carbon atom forming a vicinal di-halide.

Η
Η
Η
Η
Χ
Η
* . .
Η-
-Η
–
X
+
H-
-Η
hy
Η
Η
Η
Η
Η
Η
Η
Χ
Η

Constitutional isomers:

Any two compounds have the same chemical formula but differ in the arrangement of atoms or groups are known as constitutional isomers.

СІ СІнн
н—с
-с-с
-с
-н
н
н
н
CI
-I
-с
-с
-С-
-Н
н
н
н
н
н
н
н
н
н—с-с-с-с
-н
+ 2 СІ,
—
Сін
н.
н
н
н
н
-
С
НЕ
н
н
н
н
н
-с-с
-

-
н—с-с-с-с-н
О
н
н
н
Н
-
н
н
І
н—с
-
-с-с-с
Ет —
-н
+ 2 СІ,
—
н
н
н
н
н
CI
н
н
н
—с-с
-с
-с
-н
н
с
н
н

Ans:

The structures of the two remaining constitutional isomers are:

wt, we fou
-0-
H3CH
-OI
H3CG

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