(a) Interpretation: The IUPAC name for the given molecule is to be written. Concept introduction: When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

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Answer 1

Question

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

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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.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

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Answer 3

Question

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

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Answer 4

Question

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

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Answer 5

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 6

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 7

Chapter C, Problem C.27P

Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 14

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 15

Interpretation Introduction

(e)

Interpretation:

The IUPAC name for the given molecule is to be written.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has a higher priority. In the case of comparison between isotopes, the one having the greater atomic mass gets the 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. When writing the IPUAC name, the R or S designation is written in parenthesis for each asymmetric carbon atom and hyphens are used to separate those designations from the rest of the IUPAC name.

Answer 16

Expert Solution & Answer

Answer 17

Expert Solution & Answer

Answer 18

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Answer 19

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

Solution Summary: The author explains that the IUPAC name for the given molecule is 2-bromobutane.

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