3.

a) Synthesize the following alcohols from Grignard reagents and carbonyl compounds, giving all
reagents used in the reaction steps.

i) 2-Methyl-2-propanol

ii) 4-Methyl-1-pentanol

Answer:

i)

ii)

b) Compare and contrast between nucleophilic addition reaction and nucleophilic acyl substitution
reaction, emphasizing on reaction mechanisms and giving examples.

Answer

Nucleophilic addition reaction and nucleophilic acyl substitution reaction are two types of organic
reactions that involve the participation of a nucleophile. Although both reactions involve the attack of a
nucleophile on an electrophilic center, they differ in terms of their reaction mechanisms and the
functional groups involved.

Nucleophilic Addition Reaction:

Nucleophilic addition reactions occur when a nucleophile attacks an electrophilic center, resulting in the
addition of the nucleophile to the substrate molecule. These reactions are commonly observed in
compounds with double or triple bonds, such as alkenes or alkynes. The reaction mechanism typically
involves the following steps:

a. The nucleophile approaches the electrophilic center (e.g., a carbon-carbon double bond) and donates
its electron pair.

b. The electrophilic center forms a new bond with the nucleophile, breaking the existing π bond.

c. The reaction generates a new compound with a saturated functional group.

Example: The addition of hydrogen bromide (HBr) to ethene (C2H4) is a nucleophilic addition reaction.
In this case, the nucleophile is the bromide ion (Br-) and it attacks the electrophilic carbon atom of the
double bond in ethene. The result is the formation of bromoethane (C2H5Br).

Nucleophilic Acyl Substitution Reaction:

Nucleophilic acyl substitution reactions occur when a nucleophile replaces a leaving group in an acyl
group (R-C=O). These reactions are commonly observed in compounds containing acyl derivatives, such
as carboxylic acids, acid halides, acid anhydrides, and esters. The reaction mechanism typically involves
the following steps:

a. The nucleophile attacks the carbonyl carbon of the acyl group, leading to the formation of a
tetrahedral intermediate.

b. The leaving group (usually a halide or an alcohol) departs, resulting in the formation of a new bond
between the nucleophile and the carbonyl carbon.

c. The reaction generates a new compound with a substituted acyl group.

Example: The reaction between acetic acid (CH3COOH) and ammonia (NH3) is a nucleophilic acyl
substitution reaction. In this case, the nucleophile is the ammonia molecule, and it replaces the leaving
group (OH) in the acetic acid molecule. The result is the formation of acetamide (CH3CONH2).

In summary, nucleophilic addition reactions involve the addition of a nucleophile to a substrate, typically
a compound with double or triple bonds. On the other hand, nucleophilic acyl substitution reactions
involve the substitution of a leaving group in an acyl derivative. The reaction mechanisms and the
functional groups involved in these reactions are distinct, leading to different products.

e) Why is acetic acid stronger acid than ethanol? Justify.

answer

Acetic acid is a stronger acid than ethanol because the acetate ion formed by ionization is stabilized by
resonance while the ethoxide ion has no resonance.