Chapter 17.2, Problem 17.1P

(a)

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups.

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.

(b)

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid. If two or more carboxylic functional groups are present in the same compound then its number should be taken in to consideration and the prefix di, tri, tetra.. must be used.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

  E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.

  In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight. If the higher priority groups are on the same sides, then the configuration is designated as Z. If the higher priority groups are on the opposite sides, then the configuration is designated as E.

(c)

Interpretation Introduction

Interpretation: The IUPAC name for the compound has to be given and its configuration should be specified.

Concept introduction:

Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,

Nomenclature of carboxylic acid:

• Find the Parent hydrocarbon chain.
• Carboxyl carbon must be numbered first.
• Replace the –e in the alkane name with –oic acid.

Naming of compounds with two functional groups;

If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.

  $\begin{array}{ccc}\text{Class}& \text{Suffix name}& \text{Prefix name}\\ \text{Carboxylic acid}& \text{-oic acid}& \text{Carboxy}\\ \text{Ester}& \text{-oate}& \text{Alkoxy carbonyl}\\ \text{Amide}& \text{-amide}& \text{Amido}\\ \text{Nitrile}& \text{-ntrile}& \text{Cyano}\\ \text{Aldehyde}& \text{-al}& \text{Oxo(=O)}\\ \text{Aldehyde}& \text{-al}& \text{Formyl(-CH=O)}\\ \text{Ketone}& \text{-one}& \text{Oxo(=O)}\\ \text{Alcohol}& \text{-ol}& \text{Hydroxy}\\ \text{Amine}& \text{-amine}& \text{Amino}\\ \text{Alkene}& \text{-ene}& \text{Alkenyl}\\ \text{Alkyne}& \text{-yne}& \text{Alkynyl}\\ \text{Alkane}& \text{-ane}& \text{Alkyl}\\ \text{Ether}& \text{---}& \text{Alkoxy}\\ \text{Alkylhalide}& \text{---}& \text{Halo}\end{array}$

R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.

The CIP rules are as follows:

Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.

If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.