(a) Interpretation: The complete mechanism and the major organic product are to be drawn for the given reaction. Concept introduction: Haloforms ( CHX 3 , X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product. If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

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Answer 1

Question

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ

2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O

Answer 2

Question

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

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Answer 3

Question

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

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Answer 4

Question

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

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Answer 5

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 6

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 7

Chapter 12, Problem 12.27P

Interpretation Introduction

(a)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The complete mechanism and the major organic product are to be drawn for the given reaction.

Concept introduction:

Haloforms (CHX3, X = halogen) can be deprotonated by strong bases like alkoxide ions. The resulting tri halo anion undergoes heterolysis to produce a dihalo-carbene. The dihalo-carbene can react with an alkene or alkyne to produce a dihalo-substituted cyclopropane (or cyclopropene) ring. The lone pair of the carbene forms a bond with one of the initially double-bonded carbons. Simultaneously, the π bond pair from the alkene/alkyne forms a bond with the carbene carbon. The cis/trans stereochemistry of the starting alkene is preserved. If the alkene has a cis geometry, the two substituents are on the same side of the ring in the product. If it has a trans geometry, the two substituents are on the opposite sides of the ring in the product.

If the starting alkene is achiral and the product chiral, then a racemic mixture of two enantiomers is produced. If the starting alkene and the product are both chiral, an unequal mixture of enantiomers is produced.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 12 - Prob. 12.1P Ch. 12 - Prob. 12.2P Ch. 12 - Prob. 12.3P Ch. 12 - Prob. 12.4P Ch. 12 - Prob. 12.5P Ch. 12 - Prob. 12.6P Ch. 12 - Prob. 12.7P Ch. 12 - Prob. 12.8P Ch. 12 - Prob. 12.9P Ch. 12 - Prob. 12.10P

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