Chapter 17, Problem 17.9P

(a)

Interpretation Introduction

Interpretation: The IUPAC name for Megatomoic acid has to be given.

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.

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

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.

(b)

Interpretation Introduction

Interpretation: The number of possible stereoisomers for the given compound has to be stated.

Concept introduction:

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

The stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in different in each isomer.

The two molecules are described as stereoisomers if they are made of the same atoms connected in the same sequence, but the atoms are positions differently in space

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.