(a) Interpretation: The configuration of each stereo center in the given molecule is to be designated as R or S. Concept introduction: When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R. When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S. If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S. If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

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Answer 1

Question

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

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Please help me answer these three questions. Required info should be in data table.

Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Bri CH3CH2O- (conc.) Draw the major organic product or products.

Tartaric acid (C4H6O6) is a diprotic weak acid. A sample of 875 mg tartaric acid are dissolved in 100 mL water and titrated with 0.994 M NaOH. How many mL of NaOH are needed to reach the first equivalence point? How many mL of NaOH are needed to reach the second equivalence point?

Answer 2

Question

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

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Answer 3

Question

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

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Answer 4

Question

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

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Answer 5

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 6

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 7

Chapter C, Problem C.5P

Interpretation Introduction

(a)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituent is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The configuration of each stereo center in the given molecule is to be designated as R or S.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged clockwise, the configuration is R.

When the fourth priority substituent is pointing away (it is attached by a dash bond) and the first, second, and third priority substituents are arranged counterclockwise, the configuration is S.

If the fourth priority substituent is attached by a wedge bond, then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

If the fourth priority substituent is in the plane of the page, then it is switched with the substituent that points away. Then the clockwise or counterclockwise arrangement of the first, second, and third priority substituents is determined and that arrangement is reversed before assigning R or S.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. C - Prob. C.1P Ch. C - Prob. C.2P Ch. C - Prob. C.3P Ch. C - Prob. C.4P Ch. C - Prob. C.5P Ch. C - Prob. C.6P Ch. C - Prob. C.7P Ch. C - Prob. C.8P Ch. C - Prob. C.9P Ch. C - Prob. C.10P

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Chapter C Solutions