For the given transformations, efficient synthesis should be proposed. Concept introduction: When approaching a synthesis problem two questions should be asked 1. Is there a change in the carbon skeleton? 2. Is there a change in the position or identity of the functional group When approaching a synthesis problem, should not encounter a one-step method The desired transformation can achieve in two steps There are two ways to introduce functionality at a benzylic position 1. Oxidation, which produces benzoic acid at benzylic position 2. Radical bromination, which produces benzylic halide.

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Answer 1

Question

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

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Answer 2

Question

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

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Answer 3

Question

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

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Answer 4

Question

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

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Answer 5

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

Answer 6

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

Answer 7

Chapter 18.6, Problem 20PTS

(a)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

1. Is there a change in the carbon skeleton?

2. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

1. Oxidation, which produces benzoic acid at benzylic position

2. Radical bromination, which produces benzylic halide.

Answer 8

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

Answer 9

(b)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

3. Is there a change in the carbon skeleton?

4. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

3. Oxidation, which produces benzoic acid at benzylic position

4. Radical bromination, which produces benzylic halide.

Answer 10

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

Answer 11

(c)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

5. Is there a change in the carbon skeleton?

6. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

5. Oxidation, which produces benzoic acid at benzylic position

6. Radical bromination, which produces benzylic halide.

Answer 12

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

Answer 13

(d)

Interpretation Introduction

Interpretation: For the given transformations, efficient synthesis should be proposed.

Concept introduction:

When approaching a synthesis problem two questions should be asked

7. Is there a change in the carbon skeleton?

8. Is there a change in the position or identity of the functional group

When approaching a synthesis problem, should not encounter a one-step method

The desired transformation can achieve in two steps

There are two ways to introduce functionality at a benzylic position

7. Oxidation, which produces benzoic acid at benzylic position

8. Radical bromination, which produces benzylic halide.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 18.2 - Prob. 1LTS Ch. 18.2 - Prob. 1PTS Ch. 18.2 - Prob. 2ATS Ch. 18.2 - Prob. 3ATS Ch. 18.2 - Prob. 4ATS Ch. 18.2 - Prob. 5ATS Ch. 18.4 - Prob. 6CC Ch. 18.4 - Prob. 8CC Ch. 18.4 - Prob. 9CC Ch. 18.5 - Prob. 10CC

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Chapter 18 Solutions