(a) Interpretation: The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted. Concept introduction: When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC - in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC - adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

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Answer 1

Question

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

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3. Consider the compounds below and determine if they are aromatic, antiaromatic, or non-aromatic. In case of aromatic or anti-aromatic, please indicate number of I electrons in the respective systems. (Hint: 1. Not all lone pair electrons were explicitly drawn and you should be able to tell that the bonding electrons and lone pair electrons should reside in which hybridized atomic orbital 2. You should consider ring strain- flexibility and steric repulsion that facilitates adoption of aromaticity or avoidance of anti- aromaticity) H H N N: NH2 N Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic TT electrons Me H Me Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic πT electrons H HH…

A chemistry graduate student is studying the rate of this reaction: 2 HI (g) →H2(g) +12(g) She fills a reaction vessel with HI and measures its concentration as the reaction proceeds: time (minutes) [IH] 0 0.800M 1.0 0.301 M 2.0 0.185 M 3.0 0.134M 4.0 0.105 M Use this data to answer the following questions. Write the rate law for this reaction. rate = 0 Calculate the value of the rate constant k. k = Round your answer to 2 significant digits. Also be sure your answer has the correct unit symbol.

Answer 2

Question

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

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Answer 3

Question

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

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Answer 4

Question

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

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Answer 5

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Answer 6

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Answer 7

Chapter 18, Problem 18.4P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism for the given reaction is to be drawn, and the products are to be predicted.

Concept introduction:

When a ketone or an aldehyde is treated with aqueous hydrocyanic acid (HCN), the product is a cyanohydrin, in which an OH group and a cyano (CN) group are bonded to the same carbon atom. The reaction can be sped up by the addition of a small amount of either KCN or the strong base NaOH by increasing the concentration of NC- in the reaction mixture. The mechanism involves two steps. In the first step, the nucleophile NC- adds to the carbonyl carbon, forming an alkoxide. In the second step, a proton is transferred from the protic solvent to the alkoxide ion, giving the final product.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains the complete and detailed mechanism for the given reaction, and the products are to be predicted.

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Chapter 18 Solutions