Illustrate how cyclopentanecarboxamide can be converted into cyclopentyl isopropyl ketone involving nitrile as an intermediate. Use any necessary reagents.

Predict the product formed when a nitrile is reacted with an organolithium reagent followed by acid workup.

Using the box out method, predict the product of a Wittig reaction between benzaldehyde and methylenetriphenylphosphorane.

What characterizes the structure of an ylide in the Wittig reaction?

What is the significance of converting betaine to oxaphosphetane in the Wittig reaction?

Consider the acetal hydrolysis mechanism shown below: 

Draw the alternative mechanism where the methoxy oxygen is protonated and cleaved first, followed by the ring cleavage.

Suggest a mechanism for the pinacol rearrangement reaction given below.

Draw the product of the following pinacol rearrangement reaction.