Chapter 17, Problem 17.52AP

(a)

Interpretation Introduction

Interpretation:

The name and structure of three different amides with formula $C_5{H}_{11}NO$ has to be determined.

Concept Introduction:

Amide: One $-N{H}_2$, $-NHR\text{'}$ or $-NR{\text{'}}_2$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCONR{\text{'}}_2$.

Depending on the number of carbon side chain of the amide, different types of amides can form.

Primary amides can be named in the IUPAC system in several ways,

For simple amides the suffix – amide is added to the name of the alkyl substituent.

The suffix- amide can be used in place of the final –e in the name of the parent compound.

For a secondary amides an N prefixes the compound giving the shorter carbon chain and its chain prefix name.

For a tertiary amides an N, N prefixes the compound giving the two shorter carbon chains and their side chain prefix names.

Ammonium salt is formed when tertiary amine and a carboxylic acid reacts forming an ionic compound with a carboxylate acid anion and a trialkyl ammonium cation since there is no hydrogen atom in trialkyl amine

(b)

Interpretation Introduction

Interpretation:

The name and structure of three different esters with formula $C_6{H}_{12}{O}_2$ has to be determined.

Concept Introduction:

In chemistry structure is the arrangement of chemical bonds between atoms in a molecule, specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.

According to IUPAC nomenclature, the naming of compound is determined by the priority of the functional group if more than one functional group is present. The carbon attached to the functional group having most priority should get the least number while naming the compound.

The order of priority is,

$\begin{array}{l}\text{carboxylic}\text{acid>esters>amides>aldehydes>ketones>}\text{alcolhols>thiols>}\text{amines}\text{>}\\ \text{ethers>alkenes>alkyl}\text{halides>alkanes}\end{array}$

Carboxylic acid: One $-OH$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOH$

Ester: One $-OR\text{'}$ group is attached to the carbonyl carbon atom of the compound. It is represented as $RCOOR\text{'}$. The hydrogen atom of $-COOH$ is replaced by an alkyl group.

In case of carboxylic esters “–oic acid”is replaced by “esters “-oate” is to be written. The first part of the name indicates the alkyl group in the $RCO-$ part. The second part is the parent acid it is the alkyl group which replaces the hydrogen on the $-COOH$