Updated By SaraNextGen

On March 11, 2024, 11:35 AM

Question 11.23:

Give IUPAC names of the following ethers:

(i)

(ii)

(iii)

(iv)

(v)

(vi)

Answer:

(i) 1-Ethoxy-2-methylpropane

(ii) 2-Chloro-1-methoxyethane

(iii) 4-Nitroanisole

(iv) 1-Methoxypropane

(v) 4-Ethoxy-1, 1-dimethylcyclohexane

(vi) Ethoxybenzene

Question 11.24:

Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis:

(i) 1-Propoxypropane

(ii) Ethoxybenzene

(iii) 2-Methoxy-2-methylpropane

(iv) 1-Methoxyethane

Answer:

(i) 

(ii)

(iii)

(iv)

Question 11.25:

Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.

Answer:

The reaction of Williamson synthesis involves S_N2 attack of an alkoxide ion on a primary alkyl halide.

But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then elimination would compete over substitution. As a result, alkenes would be produced. This is because alkoxides are nucleophiles as well as strong bases. Hence, they react with alkyl halides, which results in an elimination reaction.

Question 11.26:

How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.

Answer:

1-propoxypropane can be synthesized from propan-1-ol by dehydration.

Propan-1-ol undergoes dehydration in the presence of protic acids (such as H₂SO₄, H₃PO₄) to give 1-propoxypropane.

The mechanism of this reaction involves the following three steps:

Step 1: Protonation

Step 2: Nucleophilic attack

Step 3: Deprotonation

Question 11.27:

Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.

Answer:

The formation of ethers by dehydration of alcohol is a bimolecular reaction (S_N2) involving the attack of an alcohol molecule on a protonated alcohol molecule. In the method, the alkyl group should be unhindered. In case of secondary or tertiary alcohols, the alkyl group is hindered. As a result, elimination dominates substitution. Hence, in place of ethers, alkenes are formed.

Question 11.28:

Write the equation of the reaction of hydrogen iodide with:

(i) 1-propoxypropane

(ii) Methoxybenzene and

(iii) Benzyl ethyl ether

Answer:

(i)

(ii)

(iii)

Question 11.29:

Explain the fact that in aryl alkyl ethers

(i) The alkoxy group activates the benzene ring towards electrophilic substitution and

(ii) It directs the incoming substituents to ortho and para positions in benzene ring.

Answer:

(i)

In aryl alkyl ethers, due to the +R effect of the alkoxy group, the electron density in the benzene ring increases as shown in the following resonance structure.

Thus, benzene is activated towards electrophilic substitution by the alkoxy group.

(ii) It can also be observed from the resonance structures that the electron density increases more at the ortho and para positions than at the meta position. As a result, the incoming substituents are directed to the ortho and para positions in the benzene ring.

Question 11.30:

Write the mechanism of the reaction of HI with methoxymethane.

Answer:

The mechanism of the reaction of HI with methoxymethane involves the following steps:

Step1: Protonation of methoxymethane:

Step2: Nucleophilic attack of I^−:

Step3:

When HI is in excess and the reaction is carried out at a high temperature, the methanol formed in the second step reacts with another HI molecule and gets converted to methyl iodide

Question 11.31:

Write equations of the following reactions:

(i) Friedel-Crafts reaction−alkylation of anisole.

(ii) Nitration of anisole.

(iii) Bromination of anisole in ethanoic acid medium.

(iv) Friedel-Craft’s acetylation of anisole.

Answer:

(i)

(ii)

(iii)

(iv)

Question 11.32:

Show how would you synthesise the following alcohols from appropriate alkenes?

(i)

(ii)

(iii)

(iv)

Answer:

The given alcohols can be synthesized by applying Markovnikov’s rule of acid-catalyzed hydration of appropriate alkenes.

(i)

(ii)

(iii)

Acid-catalyzed hydration of pent-2-ene also produces pentan-2-ol but along with pentan-3-ol.

Thus, the first reaction is preferred over the second one to get pentan-2-ol.

(iv)

Question 11.33:

When 3-methylbutan-2-ol is treated with HBr, the following reaction takes

place:

Give a mechanism for this reaction.

(Hint : The secondary carbocation formed in step II rearranges to a more

stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.

Answer:

The mechanism of the given reaction involves the following steps:

Step 1: Protonation

Step 2: Formation of 2° carbocation by the elimination of a water molecule

Step 3: Re-arrangement by the hydride-ion shift

Step 4: Nucleophilic attack