
Concept explainers
(a)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the nucleophilic substitution reaction, the
In
The rate determination step is formation of carbocation.
The stability order of carbocation is,
Tertiary > Secondary > Primary
Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes
In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.
In
Reactant and nucleophile are present at the rate determination step.
The order of species involving in
Tertiary < Secondary < Primary
Tosylation reaction:
The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) to yields tosylated product, this reaction is called as tosylation and which is shown below,
(a)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The given Compound (A) is reaction with methane sulfonyl chloride which gives compound (B). This compound (B) reaction with acetate ion and gives the propyl acetate (D). The reaction is given below,
(b)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.
In
The rate determination step is formation of carbocation.
The stability order of carbocation is,
Tertiary > Secondary > Primary
Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes
In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.
In
Reactant and nucleophile are present at the rate determination step.
The order of species involving in
Tertiary < Secondary < Primary
This is shown below,
(b)

Answer to Problem 55P
The product is given below,
Explanation of Solution
Alcohol (A) is reaction with
(c)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.
In
The rate determination step is formation of carbocation.
The stability order of carbocation is,
Tertiary > Secondary > Primary
Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes
In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.
In
Reactant and nucleophile are present at the rate determination step.
The order of species involving in
Tertiary < Secondary < Primary
Tosylation reaction:
The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) to yields tosylated product, this reaction is called as alkyl tosylation and which is shown below,
(c)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The given Compound (A) is reaction with para toluene sulfonyl chloride which gives compound (B). This compound (B) reaction with phenoxide ion and gives the corresponding ether (D). The reaction is given below,
(d)
Interpretation:
The product of given reaction should be given.
Concept introduction:
Dehydration reaction:
Removal of water molecule, when the alcohol is treated with strong acid like sulfuric acid is known as dehydration reaction.
The stability of carbocation is given below,
Tertiary carbocation is more stable than the secondary and primary.
(d)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The Compound (A) is undergoes dehydration, because the formation of primary carbocation and it is less stable which forms secondary carbocation and the hydrogen is removed from adjacent β- carbon atom which leads to the formation of alkene (B).
(e)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the presence of acid catalyst, this reaction takes place through partial
Epoxides are reactive, methoxide ion attacks Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.
(e)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The reaction is shown below,
Epoxides are reactive, methoxide ion attacks the Epoxides (A) in a less sterically hindered position which forms the alkoxide ion (B), then it gets proton from alcohol which form the product (C). Therefore the major product is shown above.
(f)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the presence of acid catalyst, this reaction takes place through partial
Epoxides are reactive, methoxide ion attacks theEpoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.
(f)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The reaction is shown below,
In the presence of acid catalyst, this reaction takes place through partial
(g)
Interpretation:
The product of given reaction should be given.
Concept introduction:
In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.
In
The rate determination step is formation of carbocation.
The stability order of carbocation is,
Tertiary > Secondary > Primary
Therefore, tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergoes
In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.
In
Reactant and nucleophile are present at the rate determination step.
The order of species involving in
Tertiary < Secondary < Primary
Chlorination reaction:
The alcohol is treated with thionyl chloride to yields chlorinated product, this reaction is called as chlorination and which is shown below,
(g)

Answer to Problem 55P
The product is given below,
Explanation of Solution
The given Compound (A) is reaction with thionyl chloride which gives compound (B). This compound (B) reaction with chlorine ion and gives the corresponding chloro compound (C). The reaction is given below,
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Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
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