Question

$(C{H}_3{)}_{3}C-\stackrel{\stackrel{O}{||}}{C}-N{H}_2\underset{\left(ii\right)D_{2}O}{\overset{\left(i\right)O{D}^{-}/B{r}_2}{\to }}$ Product P is

• A. $(C{H}_3{)}_{3}CN{H}_2$
• B. $(C{H}_3{)}_{3}CNHD$
• C. $(C{H}_3{)}_{3}CN{D}_2$
• D. No reaction

Answer 1

The correct option is C

$(C{H}_3{)}_{3}CN{D}_2$

Remember that in Hoffmann rearrangement, the two original H atoms of the -$CON{H}_2$ group are removed by base (OH) and new H's are derived from $H_{2}O$

$(C{H}_3{)}_{3}C-\stackrel{\stackrel{O}{||}}{C}-N{H}_2\underset{\left(ii\right)D_{2}O}{\overset{\left(i\right)O{D}^{-}/B{r}_2}{\to }}(C{H}_3{)}_{3}C-N{D}_2$