Q38E - Organic Chemistry (Mcmurry)

Question

Despite the limitations of radical chlorination of alkanes, the reaction is still useful for synthesizing certain halogenated compounds. For which of the following compounds does radical chlorination give a single monochloro product?

Step-by-Step Solution

Answer

(d) Not give single monochlorinated product.

Step 1: Radical chlorination

The reaction of chlorine with ethane in the presence of UV light or heat is an example of chlorination of alkane which results in the formation of ethyl chloride and HCl

Step 2: Chlorination of ethane

As in ethane, only one kind of C-H bond is present. So, the radical chlorination of ethane gives a single mono chloro product which is as shown:

Step 3: Chlorination of propane

There are two kinds of C-H bonds present in propane, one is CH₂ and the other is CH₃. Thus, two types of chlorinated monochlorinated products are formed. So, the radical chlorination of propane does not give a single monochloro product as shown:

Step 4: Chlorination of cyclohexane

Only one kind of C-H bond is present in cyclohexane. So, the radical chlorination of cyclohexane gives a single monochloro product as shown:

Step 5: Chlorination of given compound

As there are three different kinds of C-H bond present in the given compound, i.e., one is CH₃ attached to C, the other CH₂ is attached to C, and attached CH₃ to CH₂ as shown:

So, the radical chlorination of the given compound does not give single monochloro product.

Step 6: Chlorination of 2-butyne

Only one kind of C-H bond is present in 2-butyne, i.e.CH₃ So, the radical chlorination of 2-butyne gives a single monochloro product as shown:

Step 7: Chlorination of given compound

Only one kind of C-H bond is present in the given compound, i.e.CH₃. So, the radical chlorination of the compound gives a single monochloro product as shown: