Chapter 16, Problem 31P

(a) The cis isomer of $\text{3-hexen-1-ol}$

( ${\text{CH}}_3{\text{CH}}_2{\text{CH=CHCH}}_2{\text{CH}}_2\text{OH}$) has the characteristic odour of green leaves and grass. Suggest a synthesis for this compound from acetylene and any necessary organic or inorganic reagents.

(b) One of the compounds responsible for the characteristic odour of ripe tomatoes is the cis isomer of ${\text{CH}}_3{\text{CH}}_2{\text{CH=CHCH}}_2\text{CH=O}$. How could you prepare this compound?