Question

Ethyl acetate can be prepared by an SN2 reaction. Draw the alkylbromide and nucleophile used in the reaction. Remember to include formal charges (do not include counterions).

Answer 1

Answer:

Few important points related to $S_N2$ reaction:

1. $S_N2$ is a one-step reaction that follows second order kinetics.

2. In $S_N2$ reaction, a transition state is formed in situ.

3. Strong nucleophiles like $OH^- \ or\ CN^-$ are used in case of bi-molecular nucleophilic substitution reaction.

Ethyl acetate can be prepared by a second-order nucleophilic substitution reaction between acetic acid and ethyl bromide.  

The reaction between acetic acid and ethyl bromide is drawn below:

Answer 2

Answer:

Acetic acid + 1-chloropropane -> Ethyl acetate

Alkylbromide: 1-chloropropane

Nucleophile: Acetic acid

Explanation:

For this reaction the nucleophile would be the acetate produced by the acetic acid. Then the negative charge would attack the primary carbon on the alkyl bromide at the same time the Cl would leaves. The C-Cl bond would be broken and the C-O would be formed at the same time (see figure).

Finally the ethyl acetate is produced by the Sn2 reacion.