Chapter 15, Problem 15.74P

A and B, isomers of molecular formula ${\text{C}}_{\text{3}}{\text{H}}_{\text{5}}{\text{Cl}}_{\text{3}}$, are formed by the radical chlorination of a dihalide C of molecular formula ${\text{C}}_{\text{3}}{\text{H}}_{\text{6}}{\text{Cl}}_{\text{2}}$.

a. Identify the structures of A and B from the following ${}^1\text{H}$ NMR data:

Compound A: singlet at $2.23$ and singlet at $4.04$ ppm

Compound B: doublet at $1.69$, multiplet at $4.34$ and doublet at $5.85$ ppm

b. What is the structure of C?