Q50 E - Organic Chemistry (Mcmurry)

Question

21-50 Answer Problem 21-48 for the reaction of the listed reagents with propanamide

Step-by-Step Solution

Answer

 a.  There is no reaction, $\text{Propanamide }+Li{\left(Ph\right)}_{2}Cu$ in ether.

Introduction to the Concept

A chemical compound's structural formula is a graphic depiction of the molecular structure (derived by structural chemistry methods) that shows how the atoms might be organised in real three-dimensional space.

Solution Explanation

a)

The Gilman reagent does not cause an amide to be reduced.

Solution Explanation

b)

Through a nucleophilic acyl substitution process, the reagent Lithium Aluminum Hydride  $\mathbf{Li}\mathbf{Ae}{\mathbf{H}}_{\mathbf{4}}$ reduces the amide's acyl carbon.

The first hydride edition was followed by hydrolysis in terms of mechanism. Produces an aldehyde, which is then subjected to a second hydride reduction, resulting in the main alcohol propane-1-ol as the end product.

An amide is converted to an I alcohol by hydride reduction by $\mathbf{Li}\mathbf{Ae}{\mathbf{H}}_{\mathbf{4}}$ .

Solution Explanation

c)

An amide is converted to a $\left(3^o\right)$ tertiary alcohol with two identical substituents using Grignard reagents such as methyl magnesium bromide. (has a$C{H}_3$)

Using the Grignard Reagent, the reaction finally becomes a nucleophilic acyl substitution reaction at the acyl carbon, resulting in the reduction of carbonyl oxygen $C=O\mathit{ }to\mathit{ }C-OH$.

Because ketones are more sensitive to nucleophiles than amides, the first stage of the reaction yields a methyl propyl ketone, which is not separated. This intermediate ketone quickly adds an anomer molecule of the grignard reagent and then hydrolyzes to 2-methyl-butan-2-ol, a reduced 3° tertiary alcohol.

With two identical alkyl substitutions, a grignard reaction converts an amide to a 3° alcohol.

Solution Explanation

d)

A nucleophilic acyl substitution process converts an amide to a carboxylic acid by acidic hydrolysis.

Overall, an amide has been transformed to a carboxylic acid by an acid catalysis reaction including nucleophilic acyl substitution.

Solution Explanation

e)

Esters are formed when amides react with alcohols. As seen below, the reaction finally becomes a nucleophilic acyl substitution reaction.

When an amide is transformed to an ester, it undergoes nucleophilic acyl substitution.

Solution Explanation

f)

Ammonolysis of an amide by amide results in a nucleophilic acyl substitution process that exchanges the amide Nitrogen function.

 

In a nucleophilic acyl substitution reaction, an amide has lost its amino group.

Solution Explanation

g)

Although the carboxylate anion would be attacked nucleophilically by $\mathit{C}{\mathit{H}}_3\mathit{ }\mathit{C}{\mathit{O}}_2$, the second phase of elimination is to occur at the lin level.

The presence of a good leaving group in the final elimination phase, or at least experimental conditions that allow the production of a prospective excellent leaving group in the reactant, is a key feature of a successful nucleophilic acyl substitution reaction.