(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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Identify the missing organic reactants in the following reaction: H+ X + Y OH H+ O O Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structures of the missing organic reactants X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Explanation Check Click and drag to start drawing a structure. X G 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Cente ? E

Calculate the solubility of CaF2 in g/L (Kp = 4.0 x 10-8). sp

For the following reaction with excess reagent, predict the product. Be sure your answer accounts for stereochemistry. If multiple stereocenters are formed, be sure to draw all products using appropriate wedges and dashes. 1. EtLi, Et₂O CH₁ ? 2. H₂O*

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Concept explainers

Videos

Want to see the full answer?

Chapter 12 Solutions