Chapter 17, Problem 17.55P

Draw the structure corresponding to each name.
a. propyl formate
b. butibutanoate
c. heptyl benzoate
d. N-ethylhexanamide
e. N-ethyl-N-methylheptanamide

Interpretation Introduction

(a)

Interpretation:

The structure of propyl formate should be drawn.

Concept Introduction:

The structure of organic compound is drawn in order to represent the arrangement of atoms in which they are present in a molecule.

Answer to Problem 17.55P

  

Explanation of Solution

An organic compound in which carboxy functional group that is -COOH is bonded to the carbon atom is said to be a carboxylic acid. The general formula for carboxylic acid is RCOOH or RCO₂H. When -H of the carboxylic acid is replaced by an alkyl or aryl group (-R') then it results in the formation of an ester having general formula RCOOR'.

The reaction which results in the formation of at least one ester along with water on heating acids with alcohols is said to be esterification.

So, in order to give the IUPAC name to the esters, the following steps are followed:

• The alkyl substituent from the alcohol is named first.
• The name of the parent chain from carboxylic acid part is replaced as carboxylate.

In order to write the common name of the esters, the common of acids are written from which the ester has been formed.

The given name is propyl formate where propyl name is derived from propanol and formate is derived from the name formic acid. So, the structure of propyl formate is:

  

Interpretation Introduction

(b)

Interpretation:

The structure of butyl butanoate should be drawn.

Concept Introduction:

The structure of organic compound is drawn in order to represent the arrangement of atoms in which they are present in a molecule.

Answer to Problem 17.55P

  

Explanation of Solution

An organic compound in which carboxy functional group that is -COOH is bonded to the carbon atom is said to be a carboxylic acid. The general formula for carboxylic acid is RCOOH or RCO₂H. When -H of the carboxylic acid is replaced by an alkyl or aryl group (-R') then it results in the formation of an ester having general formula RCOOR'.

The reaction which results in the formation of at least one ester along with water on heating acids with alcohols is said to be esterification.

So, in order to give the IUPAC name to the esters, the following steps are followed:

• The alkyl substituent from the alcohol is named first.
• The name of the parent chain from carboxylic acid part is replaced as carboxylate.

In order to write the common name of the esters, the common of acids are written from which the ester has been formed.

The given name is butyl butanoate where butyl name is derived from butanol and butanoate is derived from the name butanoic acid. So, the structure of butyl butanoate is:

  

Interpretation Introduction

(c)

Interpretation:

The structure of heptyl benzoate should be drawn.

Concept Introduction:

The structure of organic compound is drawn in order to represent the arrangement of atoms in which they are present in a molecule.

Answer to Problem 17.55P

  

Explanation of Solution

An organic compound in which carboxy functional group that is -COOH is bonded to the carbon atom is said to be a carboxylic acid. The general formula for carboxylic acid is RCOOH or RCO₂H. When -H of the carboxylic acid is replaced by an alkyl or aryl group (-R') then it results in the formation of an ester having general formula RCOOR'.

The reaction which results in the formation of at least one ester along with water on heating acids with alcohols is said to be esterification.

So, in order to give the IUPAC name to the esters, the following steps are followed:

• The alkyl substituent from the alcohol is named first.
• The name of the parent chain from carboxylic acid part is replaced as carboxylate.

In order to write the common name of the esters, the common of acids are written from which the ester has been formed.

The given name is heptyl benzoate where heptyl name is derived from heptanol and benzoate is derived from the name benzoic acid. So, the structure of heptyl benzoate is:

  

Interpretation Introduction

(d)

Interpretation:

The structure of N-ethylhexanamide should be drawn.

Concept Introduction:

The structure of organic compound is drawn in order to represent the arrangement of atoms in which they are present in a molecule.

Answer to Problem 17.55P

  

Explanation of Solution

An organic compound in which carboxy functional group that is -COOH is bonded to the carbon atom is said to be a carboxylic acid. The general formula for carboxylic acid is RCOOH or RCO₂H. When -OH (hydroxyl group) of the carboxylic acid is replaced by nitrogen (-N) then it results in the formation of an amide.

The reaction which results in the formation of amide along with water on heating acids with amine or ammonia is said to be amidation.

So, in order to give the IUPAC name to the amides, the rules for naming carboxylic acid is followed and -oic acid of the carboxylic acid is replaced by amide.

In order to give the name to the amide group, the following steps are followed:

• The parent (longest) alkane chain is named as for carboxylic acids.
• The -oic acid in the name is changed to -amide.
• The numbering of the chain is done in such a way that amide group and substituents gets the smaller number.
• N-alkyl is used to show each alkyl group bonded to -N atom in the name for secondary and tertiary amides.

For number of carbons atoms chain, the prefix is given as:

Carbon-1  meth

Carbon-2  eth

Carbon-3  prop

Carbon-4  but

Carbon-5  pent

Carbon-6  hex

Carbon-7  hept

Carbon-8  oct

Carbon-9  non

Carbon-10  dec

In order to write the common name of the amides, the common of acids are written from which the amide has been formed by replacing -oic acid in name from -amide.

The given name is N-ethylhexanamide where hex represents 6 carbon atoms parent chain and N-ethyl represents ethyl substituted N atom. So, the structure of N-ethylheptanamide is:

  

Interpretation Introduction

(e)

Interpretation:

The structure of N-ethyl-N-methylheptanamide should be drawn.

Concept Introduction:

The structure of organic compound is drawn in order to represent the arrangement of atoms in which they are present in a molecule.

Answer to Problem 17.55P

  

Explanation of Solution

An organic compound in which carboxy functional group that is -COOH is bonded to the carbon atom is said to be a carboxylic acid. The general formula for carboxylic acid is RCOOH or RCO₂H. When -OH (hydroxyl group) of the carboxylic acid is replaced by nitrogen (-N) then it results in the formation of an amide.

The reaction which results in the formation of amide along with water on heating acids with amine or ammonia is said to be amidation.

So, in order to give the IUPAC name to the amides, the rules for naming carboxylic acid is followed and -oic acid of the carboxylic acid is replaced by amide.

In order to give the name to the amide group, the following steps are followed:

• The parent (longest) alkane chain is named as for carboxylic acids.
• The -oic acid in the name is changed to -amide.
• The numbering of the chain is done in such a way that amide group and substituents gets the smaller number.
• N-alkyl is used to show each alkyl group bonded to -N atom in the name for secondary and tertiary amides.

For number of carbons atoms chain, the prefix is given as:

Carbon-1  meth

Carbon-2  eth

Carbon-3  prop

Carbon-4  but

Carbon-5  pent

Carbon-6  hex

Carbon-7  hept

Carbon-8  oct

Carbon-9  non

Carbon-10  dec

In order to write the common name of the amides, the common of acids are written from which the amide has been formed by replacing -oic acid in name from -amide.

The given name is N-ethyl-N-methylheptanamide where hept represents 7 carbon atoms parent chain, N-ethyl represents ethyl substituted N atom and N-methyl represents methyl substituted N atom. So, the structure of N-ethyl-N-methylheptanamide is: