Chapter 19, Problem 13P

Interpretation Introduction

Interpretation:

The structural formula corresponding to the given name has to be stated.

Concept Introduction:

The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are as follows:

First identify the word root for the given compound.

Identify the suffix used in the given compound like –ene, oic, ane, etc.

Identify the position, location, and number of the substituent bonded to the carbon chain.

Answer to Problem 13P

Solution:

a) The structural formula corresponding to the given name is shown below.

b) The structural formula corresponding to the given name is shown below.

c) The structural formula corresponding to the given name is ${\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{12}}\text{COOH}$.

d) The structural formula corresponding to the given name is ${\text{CH}}_{\text{2}}=\text{CH}{\left({\text{CH}}_{\text{2}}\right)}_{\text{8}}\text{COOH}$.

e) The structural formula corresponding to the given name is shown below.

f) The structural formula corresponding to the given name is shown below.

g) The structural formula corresponding to the given name is shown below.

h) The structural formula corresponding to the given name is shown below.

i) The structural formula corresponding to the given name is shown below.

j) The structural formula corresponding to the given name is shown below.

Explanation of Solution

a) Structural formula of $2-\text{Hydroxypropanoic}\text{acid}$.

The given name is $2-\text{Hydroxypropanoic}\text{acid}$. The word root used in this is prop. It means structure contains three carbon atoms. The groups that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One hydroxy substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.

b) Structural formula of $2\text{-Hydroxy-2-phenylethanoic}\text{acid}$.

The given name is $2\text{-Hydroxy-2-phenylethanoic}\text{acid}$. The word root used in this is eth. It means structure longest carbon chain contains two carbon atoms. One hydroxy and one phenyl substituents is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.

c) Structural formula of tetradecanoic acid.

The given name is tetradecanoic acid. The word root used in this is tetradec. It means structure contains fourteen carbon atoms. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is ${\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{12}}\text{COOH}$.

d) Structural formula of $10-\text{Undecenoic}\text{acid}$.

The given name is $10-\text{Undecenoic}\text{acid}$. The word root used in this is undec. It means structure contains eleven carbon atoms. The structural formula corresponding to the given name is ${\text{CH}}_{\text{2}}=\text{CH}{\left({\text{CH}}_{\text{2}}\right)}_{\text{8}}\text{COOH}$.

e) Structural formula of $3,5\text{-Dihydroxy-3-methylpentanoic}\text{acid}$.

The given name is $3,5\text{-Dihydroxy-3-methylpentanoic}\text{acid}$. The word root used in this is pent. It means longest carbon chain of the structure contains five carbon atoms. One hydroxy substituent is attached to the third and fifth carbon atom. One methyl substituent is also attached to the third carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.

f) Structural formula of $\left(E\right)\text{-2-Methyl-2-butenoic}\text{acid}$.

The given name is $\left(E\right)\text{-2-Methyl-2-butenoic}\text{acid}$. The word root used in this is but. It means the longest carbon chain in the structure contains four carbon atoms. One methyl substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The prefix $E$ and $Z$ depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an $E$ isomer, whereas when two higher priority groups are present on the same side then it is $Z$ isomer. The structural formula corresponding to the given name is shown below.

g) Structural formula of $2-\text{Hydroxybutanedioic}\text{acid}$.

The given name is $2-\text{Hydroxybutanedioic}\text{acid}$. The word root used in this is but. It means the longest carbon chain in the structure contains four carbon atoms. One hydroxy substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.

h) Structural formula of $2-\text{Hydroxy-1,2,3-propanetriccarboxylic}\text{acid}$.

The given name is $2-\text{Hydroxy-1,2,3-propanetriccarboxylic}\text{acid}$. The word root used in this is prop. It means longest carbon chain contains three carbon atoms. One hydroxy substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The structural formula corresponding to the given name is shown below.

i) Structural formula of $\text{2-}\left(p\text{-isobutylphenyl}\right)\text{propanoic}\text{acid}$.

The given name is $\text{2-}\left(p\text{-isobutylphenyl}\right)\text{propanoic}\text{acid}$. The word root used in this is prop. It means the longest carbon chain contains three carbon atoms. One isobutyl phenyl substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.

j) Structural formula of $o-\text{Hydroxybenzenecarboxylic}\text{acid}$.

The given name is $o-\text{Hydroxybenzenecarboxylic}\text{acid}$. The word root used in this is benzene. It means structure contain one cyclic ring. One hydroxy substituent is attached to the second carbon atom. The functional group present in the given compound is carboxylic acid $\left(\text{COOH}\right)$. The suffix used for carboxylic acid is -oic. The structural formula corresponding to the given name is shown below.