Q49dE - Organic Chemistry (Mcmurry)

Question

Question:  Propose structures for compounds that fit the following descriptions: 

(d) An alcohol that reacts rapidly with HCl at 0 °C

Step-by-Step Solution

Answer

Answer: 

Step 1: S N 2 reaction

It is a nucleophilic substitution reaction in which an old bond is broken, and a new bond is formed. Both processes co-occur. Hence, it’s a single-step reaction.

The two reacting species are involved in the rate-determining steps.

Step 2: Nucleophile

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons ready for bonding.

Step 3: Reaction to alcohol

When an alkyl halide reacts with alcohol, it undergoes a substitution reaction because halides are more nucleophilic. The reaction occurs fast with tertiary alcohol because they are bulky; hence, substitution occurs quickly.