The actual oxidizing agent and the function of the other reagents. Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated. Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Question

Want to see the full answer?

Answer 1

Question

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. QA O • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. • If enantiomers are formed, draw both. • Separate multiple products using the + sign from the drop-down menu. P aste ChemDoodleⓇ ▼ [] Previous Next

The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. QAO • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. • If enantiomers are formed, draw both. • Separate multiple products using the sign from the drop-down menu. + e./ 8) 16224 000. It

Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion: CH3 H3C O Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. орy вste ChemDoodle

Answer 2

Question

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 6

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 7

Chapter 14.11B, Problem 14.21P

(a)

Interpretation Introduction

To determine: The actual oxidizing agent and the function of the other reagents.

Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 8

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 9

(b)

Interpretation Introduction

To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.

Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 10

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

Answer 11

(c)

Interpretation Introduction

To determine: The other enantiomer of the product.

Interpretation: The other enantiomer of the product is to be stated.

Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield 90 % enantiomeric excess. The reagents used in sharpless epoxidation are tert-butyl hydroperoxide, a dialkyl tartarate and titanium (IV) isopropoxide.

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. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2P Ch. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5P Ch. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8P Ch. 14.5 - Prob. 14.9P Ch. 14.6 - Prob. 14.10P

Solution Summary: The author explains the actual oxidizing agent and the function of the other reagents in catalytic asymmetric synthesis.

Want to see the full answer?

Chapter 14 Solutions