Question

synthesize 3-phenylpropanol from acetylene and benzyl bromide

Answer 1

Answer on Question #66024 - Chemistry - Organic Chemistry

Task:

Synthesize 3-phenylpropanol from acetylene and benzyl bromide

Solution:

1)

$$\begin{array}{l} \mathrm{H} \xrightarrow{\text{NH}_3} \mathrm{H} + 2 \mathrm{LiNH_2} \xrightarrow{\mathrm{NH_3} (\text{liquid})} \mathrm{H} \xrightarrow{\text{Li}} + 2 \mathrm{NH_3} \\ \text{acetylene} \\ \end{array}$$ $$\begin{array}{l} \mathrm{H} \xrightarrow{\text{NH}_3} \mathrm{H} + \mathrm{BuLi} \xrightarrow[\text{-78}^0 \text{C}]{\text{THF}} \mathrm{H} \xrightarrow{\text{Li}} + \mathrm{BuH} \\ \text{acetylene} \\ \end{array}$$

2)

$$\begin{array}{c} \mathrm{CH_3} \\ | \\ \mathrm{Br} \\ | \\ \mathrm{Br} \\ \end{array} + \mathrm{H}$$

benzyl bromide

$$\begin{array}{l} \ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } } \xrightarrow{\text{Sia}_2\text{BH}} \ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } } \ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } } \\ \text{enol} \\ \end{array}$$ $$\begin{array}{l} \ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } } \\ \ce{ \chemfig{ CH_3O} } \\ \end{array}$$ $$\begin{array}{l} \ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } } \\ 1) \frac{\mathrm{NaBH_4} \cdot \mathrm{EtOH}}{2) \mathrm{H_3O^+}} \end{array}$$ $$\ce{ \chemfig{ O= C(-[::+60]CH_3)(-[::-60]CH_3) } }$$

Answer provided by www.AssignmentExpert.com