Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 10, Problem 69P

(a)

Interpretation Introduction

Interpretation:

The appropriate reagents should be given for each steps in the given reaction.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  1

The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary and primary.

The alcohols is reaction with acids like hydrochloric acid or hydrobromic, which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes elimination reaction which yields the corresponding alkene as a product.

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  2

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

Ozonolysis:

Alkene reacts with ozone to gives aldehyde and ketone is known as ozonolysis.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  3

Oxidation of alcohol:

Alcohols reacts with hypochlorous (oxidizing agent) in the presence of acetic acid which yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  4

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  5

(b)

Interpretation Introduction

Interpretation:

The appropriate reagents should be given for each steps in the given reaction.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  6

The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary and primary.

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes elimination reaction which yields the corresponding alkene as a product.

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  7

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

Ozonolysis:

Alkene reacts with ozone which cleaves the double bond followed by work up with dimethyl sulfide to forms ketone with aldehyde is known as ozonolysis.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  8

Oxidation of alcohol:

Alcohols reaction with hypochlorous (oxidizing agent) in the presence of acetic acid which yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  9

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  10

(c)

Interpretation Introduction

Interpretation:

The appropriate reagents should be given for each steps in the given reaction.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  11

The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary and primary.

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes elimination reaction which yields the corresponding alkene as a product.

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  12

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

Ozonolysis:

Alkene reacts with ozone which cleaves the double bond followed by work up with dimethyl sulfide to forms ketone with aldehyde is known as ozonolysis.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  13

Oxidation of alcohol:

Alcohols reaction with hypochlorous (oxidizing agent) in the presence of acetic acid which yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  14

Organic Chemistry (8th Edition), Chapter 10, Problem 69P , additional homework tip  15

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Chapter 10 Solutions

Organic Chemistry (8th Edition)

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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