The product for the given reaction has to be identified. Concept introduction: Epoxides from Peroxy acids: The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific. Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The C-Mg bond in the Grignard reagent will act as the nucleophile.

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Answer 1

Question

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

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Answer 2

Question

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

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See solution

Answer 3

Question

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

Answer 6

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

Answer 7

Chapter 13, Problem 37PP

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Alkoxymercuration-demercuration: the process where alcohols can be prepared from alkene, results in the markovnikov’s addition of $H & OH$ groups across the double bond of alkene.

NaBH₄ (Sodium borohydride):

Sodium borohydride is used as a reducing agent.

Aldehydes and ketons react with sodium borohydrate undergoes reduction to forms alcohols.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

Answer 11

(c)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

Answer 12

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Answer 14

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

Answer 15

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

Epoxides from Peroxy acids:

The commonly used Peroxy acids are meta-Chloroperoxybenzoic acid (MCPBA) and Peroxyacetic acid. This process is stereospecific.

Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).

Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.

Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

Answer 16

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

Answer 17

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of Grignard reagent with epoxide will form alcohols. Grignard reagent will add to the less substituted carbon. The $C-Mg$ bond in the Grignard reagent will act as the nucleophile.

The reactions of Epoxides with strong nucleophiles requires a strong driving force that helps in the removal of ring strain associated with the three-membered ring of an Epoxide. These ring opening reactions also occur under acidic conditions.

The mechanism of acid-catalyzed ring opening of an Epoxide occurs in two steps.

In first step, the protonation of Epoxide occurs.

In second step, the attack of nucleophile occurs in the protonated Epoxide by $SN2$ process.

Answer 18

Expert Solution & Answer

Answer 19

Expert Solution & Answer

Answer 20

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Check out a sample textbook solution

See solution

Answer 21

Ch. 13.2 - Prob. 1LTS Ch. 13.2 - Prob. 1PTS Ch. 13.2 - Prob. 2PTS Ch. 13.2 - Prob. 3ATS Ch. 13.4 - Prob. 4CC Ch. 13.5 - Prob. 2LTS Ch. 13.5 - PRACTICE the skill Show reagents that you could...Ch. 13.5 - APPLY the skill Compound 2 was made as a...Ch. 13.5 - Prob. 7CC Ch. 13.5 - Prob. 8CC

Interpretation: The product for the given reaction has to be identified. Concept introduction: Reaction of metal with alcohol: Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.

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Chapter 13 Solutions

Interpretation:

The product for the given reaction has to be identified.

Concept introduction:

Reaction of metal with alcohol:

Metals can react with alcohol to produce alkoxide ion. For an example, ethanol can be react with sodium to produce hydrogen gas and sodium ethoxide.