Q7-19P - Organic Chemistry (Mcmurry)

Question

Draw a skeletal structure of the following carbocation. Identify it as primary, secondary, or tertiary, and identify the hydrogen atoms that have the proper orientation for hyperconjugation in the conformation shown.

Step-by-Step Solution

Answer

Structure of compound

Step-by-Step solution Step 1: Carbocation

Carbocations can be categorized into primary, secondary and tertiary carbocations. If one carbon is attached to the carbocation it is termed a primary carbocation.

Step 2: Identification of the skeletal structure of the carbocation and the hydrogen atoms that have proper orientation for hyperconjugation

The skeletal structure of the carbocation can be given as:

Skeletal structure of the carbocation

The carbon having the positive charge is connected to two other carbon atoms. Hence, it is secondary in nature.

The conformation comprises three methyl groups. The three hydrogens indicated with an asterisk on the methyl groups have orbitals parallel to the carbocation p orbital and hence exhibit hyperconjugation. 

Identifying the hydrogen atoms with an asterisk