The complete mechanism for this reaction is to be shown and the major product is to be predicted. Concept introduction: In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an S N 2 reaction. The result is α halogenation of the aldehyde/ketone. Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Answer 1

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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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Answer 3

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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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Answer 4

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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 10, Problem 10.13P

Interpretation Introduction