ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING.
ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING.
8th Edition
ISBN: 9780134466712
Author: Bruice
Publisher: PEARSON
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Concept explainers

Question
Chapter 10, Problem 55P

(a)

Interpretation Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

SN1reaction:

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 SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

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 SN1 substitution reaction.

SN2reaction:

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 SN2 reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in SN2 reaction is,

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  1

(a)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  2

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

SN1reaction:

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 SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

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 SN1 substitution reaction.

SN2reaction:

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 SN2 reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in SN2 reaction is,

Tertiary < Secondary < Primary

This is shown below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  4

(b)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  5

Explanation of Solution

Alcohol (A) is reaction with PBr3 in pyridine which undergoes SN2 type of reaction, the bromine attacks the carbon atom through the back side and provides brominated compound (C). This is shown below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  6

(c)

Interpretation Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

SN1reaction:

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 SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

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 SN1 substitution reaction.

SN2reaction:

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 SN2 reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in SN2 reaction is,

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  7

(c)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  8

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  9

(d)

Interpretation Introduction

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.

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  10

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  11

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).

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  12

(e)

Interpretation Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  13

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  14

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)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  15

Explanation of Solution

The reaction is shown below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  16

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 Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  17

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  18

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)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  19

Explanation of Solution

The reaction is shown below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  20

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive Epoxides (A) get protonated forms compound (B) followed by alcohol attacks to the stable carbocation and form the final product (C).

(g)

Interpretation Introduction

Interpretation:

The product of given reaction should be given.

Concept introduction:

SN1reaction:

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 SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

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 SN1 substitution reaction.

SN2reaction:

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 SN2 reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in SN2 reaction is,

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  21

(g)

Expert Solution
Check Mark

Answer to Problem 55P

The product is given below,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  22

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,

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING., Chapter 10, Problem 55P , additional homework tip  23

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Chapter 10 Solutions

ORGANIC CHEMISTRY (LL)-W/MOD.MASTERING.

Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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