Q39E - Organic Chemistry (Mcmurry)

Question

Draw all of the different monochlorinated products one would obtain by the radical chlorination of these compounds. (Do not consider the stereochemistry of the products in your answer.)

Step-by-Step Solution

Answer

(a)

(b)

(c)

Step 1: n-Butane

n-butane undergoes radical chlorination in the presence of UV light or heat to form two mono chlorinated products

Step 2: Chlorination of n-butane

In n-butane there are two types of hydrogen atoms are present. Out of the two hydrogens, one is primary and the other is secondary. So, n-butane undergoes radical chlorination and forms two mono chlorinated products as shown:

Step 3: Possible position in Isopentane

In isopentane, there are four types of hydrogens are present, as shown:

Step 4: Chlorination in isopentane

Therefore, isopentane undergoes radical chlorination to form four monochlorinated products. There are four positions are available in the Iospentane which are shown as below here:

Step 5: methyl cyclopentane

In methyl cyclopentane there are four types of hydrogens are present as shown:

Step 2: Chlorination of methyl cyclopentane

Therefore, methyl cyclopentane undergoes radical chlorination to form four monochlorinated products as shown: