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Chapter 11, Problem 75P

(a)

Interpretation Introduction

Interpretation:

The mechanism of the given reaction should be proposed.

Concept introduction:

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  1

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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  2

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.

(b)

Interpretation Introduction

Interpretation:

The structure of all products that formed in the given reaction should be drawn.

Concept introduction:

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  3

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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  4

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.

(c)

Interpretation Introduction

Interpretation:

The reason should be explained for the formation of six member ring compound in the given reaction.

Concept introduction:

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  5

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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 11, Problem 75P , additional homework tip  6

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.

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Chapter 11 Solutions

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18PCh. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20PCh. 11.6 - Prob. 22PCh. 11.7 - Prob. 24PCh. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26PCh. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28PCh. 11.7 - Prob. 29PCh. 11.7 - Prob. 30PCh. 11.8 - Prob. 31PCh. 11.8 - Prob. 32PCh. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38PCh. 11.10 - Prob. 39PCh. 11.10 - Prob. 40PCh. 11.10 - Prob. 41PCh. 11.10 - Prob. 42PCh. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54PCh. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65PCh. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71PCh. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75PCh. 11 - Prob. 76PCh. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79PCh. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82PCh. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85PCh. 11 - Prob. 86PCh. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....
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