Chapter 12, Problem 12.81QP

(a)

Interpretation Introduction

Interpretation:

Structure and IUPAC name for the reactant and product for the given reaction has to be given.

Concept Introduction:

IUPAC rules for naming alcohols:

• Alcohols are named by identifying the parent compound and replacing the –eending with –ol.
• Lowest possible number should be given for the hydroxyl group present in the parent chain.
• Name and number all substituent, and put them as prefixes to “alkanol” name also give the first preference as per the alphabetical order.
• If an alcohol contains two hydroxyl groups then name it as diol, an alcohol; contains three hydroxyl groups then name it as triol.

IUPAC rules for naming ethers:

• Ethers are characterized by $\text{R - O - R}$ functional group and which has two alkyl groups.
• Longest alkyl group in the parent chain of the molecule is named as hydrocarbon chain.
• Simplest alkyl group attached to the parent chain is named as alkoxy group.
• The numbering for chain must be done to get the lowest number for the carbon that is attached to the alkoxy group.
• The structure representation of alkoxy group is $-OR$ and which is analogous to the naming of hydroxyl group in alcohols, so ${\text{CH}}_{\text{3}}-\text{O}-$ is methoxy, ${\text{CH}}_{\text{3}}{\text{CH}}_2-\text{O}-$ is ethoxy, and so on.

Explanation of Solution

The structure for the ether formed by the reaction of given alcohol under the acidic conditions by heating can be shown as follows,

IPUAC name and common name for reactant:

Parent compound    :    ethane

Position of $-OH$    :    carbon – 1

Substituent         :    no substituent

IUPAC Name        :    ethan-1-ol (ethanol)

Therefore, the IUPAC name and common name for the given reactant is ethan-1-ol and ethanol respectively.

IPUAC name and common name for product:

Parent compound    :    ethane

Position of $-OR$    :    carbon – 1

Substituent         :    1-ethoxy

IUPAC Name        :    1-ethoxyethane

Therefore, the IUPAC name and common name for the given product is 1-ethoxyethane and diethyl ether respectively.

(b)

Interpretation Introduction

Interpretation:

Structure and IUPAC name for the reactant and product for the given reaction has to be given.

Concept Introduction:

Refer part (a).

Explanation of Solution

The structure for the ether formed by the reaction of given alcohol under the acidic conditions by heating can be shown as follows,

IPUAC name and common name for reactant:

Parent compound    :    methane, ethane

Position of $-OH$    :    carbon – 1

Substituent         :    no substituent

IUPAC Name        :    methan-1-ol (methanol), ethan-1-ol (ethanol)

Therefore, the IUPAC name and common name for the given reactant is methan-1-ol, methanol and ethan-1-ol, ethanol respectively.

IPUAC name and common name for product:

Parent compound    :    ethane

Position of     :    carbon – 1

Substituent         :    1-ethoxy

IUPAC Name        :    1-ethoxyethane

Therefore, the IUPAC name and common name for the given product is 1-ethoxyethane and diethyl ether respectively.

Parent compound    :    methane

Position of     :    carbon – 1

Substituent         :    1-methoxy

IUPAC Name        :    1-methoxymethane

Therefore, the IUPAC name and common name for the given product is 1-methoxymethane and dimethyl ether respectively.

Parent compound    :    ethane

Position of     :    carbon – 1

Substituent         :    1-methoxy

IUPAC Name        :    1-methoxyethane

Therefore, the IUPAC name and common name for the given product is 1-methoxyethane and ethyl methyl ether respectively.

(c)

Interpretation Introduction

Interpretation:

Structure and IUPAC name for the reactant and product for the given reaction has to be given.

Concept Introduction:

Refer part (a).

Explanation of Solution

The structure for the ether formed by the reaction of given alcohol under the acidic conditions by heating can be shown as follows,

IPUAC name and common name for reactant:

Parent compound    :    propane

Position of     :    carbon – 2

Substituent         :    no substituent

IUPAC Name        :    propan-2-ol (isopropyl alcohol)

Therefore, the IUPAC name and common name for the given reactant is propan-2-ol and isopropyl alcohol respectively.

Parent compound    :    methane, ethane

Position of $-OH$    :    carbon – 1

Substituent         :    no substituent

IUPAC Name        :    methan-1-ol (methanol), ethan-1-ol (ethanol)

Therefore, the IUPAC name and common name for the given reactant is methan-1-ol, methanol and ethan-1-ol, ethanol respectively.

IPUAC name and common name for product:

Parent compound    :    methane

Position of     :    carbon – 1

Substituent         :    1-methoxy

IUPAC Name        :    1-methoxymethane

Therefore, the IUPAC name and common name for the given product is 1-methoxymethane and dimethyl ether respectively.

Parent compound    :    propane

Position of     :    carbon – 2

Substituent         :    1-methoxy,

IUPAC Name        :    2-methoxypropane

Therefore, the IUPAC name and common name for the given product is 2-methoxypropane and methyl isopropyl ether respectively.

Parent compound    :    propane

Position of     :    carbon – 2

Substituent         :    2-isopropoxy,

IUPAC Name        :    2-isopropoxypropane

Therefore, the IUPAC name and common name for the given product is 2-isopropoxypropane and diisopropyl ether respectively.

(d)

Interpretation Introduction

Interpretation:

Structure and IUPAC name for the reactant and product for the given reaction has to be given.

Concept Introduction:

Refer part (a).

Explanation of Solution

The structure for the ether formed by the reaction of given alcohol under the acidic conditions by heating can be shown as follows,

IPUAC name and common name for reactant:

Parent compound    :    methylcyclopentane

Position of     :    carbon – 1

Substituent         :    no substituent

IUPAC Name        :    cyclopentylmethanol

Therefore, the IUPAC name and common name for the given reactant is cyclopentylmethanol and hydroxymethyl cyclopentane respectively.

IPUAC name and common name for product:

Parent compound    :    cyclopentane

Position of     :    carbon – 1

Substituent         :    No substituent

IUPAC Name        :    oxydicyclopentane

Therefore, the IUPAC name and common name for the given product is oxydicyclopentane and cyclopentyl ether respectively.