The given following compounds has to be prepared using an aldol addition in the first step. Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed. If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion. Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Question

Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

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Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image

2. Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. OH CH-COOH 0 HO CN C H30* C. H H HC N NaOH H₂O C=O 0 cyanohydrin H + NaCN + H₂O

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

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Answer 5

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 6

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 7

Chapter 17.12, Problem 25P

(a)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 8

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 9

(b)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 10

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 11

(c)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 12

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 13

(d)

Interpretation Introduction

Interpretation: The given following compounds has to be prepared using an aldol addition in the first step.

Concept introduction: If two different carbonyl compound used in an aldol addition, known as a crossed-aldol reaction. If the two carbonyl compounds contain alpha carbon then four products are formed because two different enolate ion is formed.

If both carbonyl compounds have alpha hydrogens, primarily only one product is formed if LDA is used to remove the alpha hydrogen from carbonyl carbon that is needed for the enolate ion.

Because LDA is a strong base, all of the carbonyl carbon is converted to the enolate ion, so none of the carbonyl carbon is left behind to react with enolate ion. Therefore, the second carbonyl compound is added slowly.

Answer 14

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Answer 25

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

Solution Summary: The author explains that the following compounds have to be prepared using an aldol addition in the first step.

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Chapter 17 Solutions