Question

Draw the curved arrow mechanism for the addition of HCN in water with NaOH to 3-methylcyclopentan-1-one to give the corresponding cyanohydrin in the fewest steps. Draw the arrows that lead to the resonance structures with full octets around each atom other than hydrogen. Draw all electrons and charges if necessary on all structures; do not show any inorganic side products or counterions. Reagents needed for each step are provided in the boxes.

Answer 1

Reaction mechanism consists of three steps which are depicted below.

Step-by-step explanation:

• In the first step, NaOH reacts with HCN to produce stronger nucleophile
  `CN^(-)`.
• In the second step,
  `CN^(-)` gives nucleophilic addition reaction at the carbonyl center of 3-methylcyclopentan-1-one.
• In the third step, alkoxy ion removes a proton from
  `H_(2)O` molecule to form cyanohydrin.
• Full mechanistic pathway has been shown below.