(a) Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated. Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH 2 are especially utilized, due to the by-product of the reaction ( H 2 or NH 3 ) .

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Answer 1

Question

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

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Explain why the ether obtained by treating an optically active alcohol with PBr3 in pyridine followed by sodium methoxide has the same configuration as the alcohol, whereas the ether obtained by treating the alcohol with tosyl chloride followed by sodium methoxide has a configuration opposite that of the alcohol.

H3C. 00 H3C. CH3 XII HO: OCH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 2 CH₂OH HCI catalyst CH3 H3C H-OH₂ H3CO OCH3 CH3 H3C. H₂O: OCH3 CH3 H₂O Ча

Draw the organic product(s) formed when CH3CH₂CH₂OH is treated with each reagent. a. H₂SO4 d. HBr g. TsCl, pyridine b. NaH h. [1] NaH; [2] CH₂CH₂Br e. SOCI₂, pyridine f. PBr3 c. HCI + ZnCl₂ Hint: NaH deprotonates the alcohol forming an alkoxide

Answer 2

Question

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

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Answer 3

Question

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

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Answer 4

Question

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

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Answer 5

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Answer 6

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Answer 7

Chapter 18, Problem 63P

Interpretation Introduction

(a)

Interpretation: A stepwise mechanism for the formation of MOM ether from cyclohexanol is to be stated.

Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-base reaction. In this reaction, NaH or NaNH2 are especially utilized, due to the by-product of the reaction (H2 or NH3).

Answer 8

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Answer 9

Interpretation Introduction

(b)

Interpretation: The functional group that MOM ether comprises is to be identified.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Answer 10

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Answer 11

Interpretation Introduction

(c)

Interpretation: The other products that are formed besides cyclohexanol from the aqueous hydrolysis of the MOM ether are to be predicted, and a stepwise mechanism for the formation of each product is to be drawn.

Concept introduction: Acetals are the groups in which carbon atom is bonded with two OR groups through single bonds. They are used as protecting groups for aldehydes and ketones as they are stable enough in neutral to strong basic condition.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 18.1 - Rank the following compounds in order of...Ch. 18.1 - Prob. 2P Ch. 18.2 - Give the IUPAC name for each aldehyde.Ch. 18.2 - Prob. 4P Ch. 18.2 - Give the IUPAC name for each ketone.Ch. 18.5 - Prob. 11P Ch. 18.9 - Problem 21.17 Draw the products of the following...Ch. 18.9 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 18.9 - Problem 21.19 Draw the products (including...Ch. 18.9 - Problem 21.20 What starting materials are needed...

Solution Summary: The author explains the stepwise mechanism for the formation of MOM ether from cyclohexanol. The alkoxide salts are prepared from alcohols through the Bronsted-Lowry acid-

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