Chapter 17, Problem 40P

Give stereochemical formulas for compounds A–Q:

(a) $\begin{array}{l}\left(\text{R}\right)\text{-}(-)\text{-}2\text{-}Bu\tan ol\underset{pyridine}{\overset{\begin{array}{l}\text{p-}toluenesulfonyl\\ chloride\left(TsCl\right)\end{array}}{\to }}A\underset{}{\overset{{}^{-}C\equiv N}{\to }}B\left(C_5{H}_{9}N\right)\underset{H_{2}O}{\overset{H_{2}S{O}_4}{\to }}\\ (+)\text{-}C\left(C_5{H}_{10}{O}_2\right)\underset{H_{2}O}{\overset{\left(1\right)LiAl{H}_4}{\to }}(-)\text{-}D\left(C_5{H}_{12}O\right)\end{array}$

(b) $\begin{array}{l}\left(\text{R}\right)\text{-}(-)\text{-}2\text{-}Bu\tan ol\underset{pyridine}{\overset{PB{r}_3}{\to }}E\left(C{4}_{}{H}_{9}Br\right)\underset{}{\overset{{}^{-}C\equiv N}{\to }}F\left(C_5{H}_{9}N\right)\underset{H_{2}O}{\overset{H_{2}S{O}_4}{\to }}\\ (-)\text{-}C\left(C_5{H}_{10}{O}_2\right)\underset{H_{2}O}{\overset{\left(1\right)LiAl{H}_4}{\to }}(+)\text{-}D\left(C_5{H}_{12}O\right)\end{array}$

(c) $A\underset{}{\overset{C{H}_{3}C{O}_2^{-}}{\to }}G\left(C_6{H}_{12}{O}_2\right)\underset{}{\overset{H{O}^{-}}{\to }}(+)\text{-}H\left(C_4{H}_{10}O\right)+C{H}_{3}C{O}_2^{-}$

(d) $(-)\text{-}D\underset{}{\overset{PB{r}_3}{\to }}J\left(C_5{H}_{11}Br\right)\underset{E{t}_{2}O}{\overset{Mg}{\to }}K\left(C_5{H}_{11}MgBr\right)\underset{\left(2\right)H_3{O}^{+}}{\overset{\left(1\right)C{O}_2}{\to }}L\left(C_6{H}_{12}{O}_2\right)$

(e)

(f) $M\underset{H_{2}O}{\overset{H_{2}S{O}_4}{\to }}P\left(C_4{H}_8{O}_5\right)\underset{HN{O}_3}{\overset{\left[O\right]}{\to }}\text{meso-}tartaricacid$

(g) $N\underset{H_{2}O}{\overset{H_{2}S{O}_4}{\to }}Q\left(C_4{H}_8{O}_5\right)\underset{HN{O}_3}{\overset{\left[O\right]}{\to }}(-)\text{-}tartaricacid$