(a) Interpretation: The structure for the given molecule is to be drawn. Concept introduction: When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.

Question

Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic. ZI NH Explanation Check O aromatic O antiaromatic O nonaromatic O aromatic O antiaromatic H O nonaromatic O aromatic O antiaromatic O nonaromatic ×

Answer 1

Question

Chapter C, Problem C.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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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Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic. ZI NH Explanation Check O aromatic O antiaromatic O nonaromatic O aromatic O antiaromatic H O nonaromatic O aromatic O antiaromatic O nonaromatic ×

Part I. Draw the stepwise reaction mechanism of each product (a, b, c, d, e, f) HO HO OH НОН,С HO OH Sucrose HO CH₂OH H N N HO -H H -OH KMnO4, Heat H OH CH₂OH (d) Phenyl Osatriazole OH НОН,С HO HO + Glacial HOAC HO- HO CH₂OH OH HO Fructose (a) Glucose OH (b) H₂N HN‍ (c) CuSO4-5H2O, ethanol H N N N HO ·H H OH H OH N CH₂OH OH (f) Phenyl Osazone H (e) Carboxy phenyl osatriazole Figure 2.1. Reaction Scheme for the Total Synthesis of Fine Chemicals

Which molecule is the most stable? Please explain.

Answer 2

Question

Chapter C, Problem C.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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.9P

Interpretation Introduction

(a)

Interpretation:

The structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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 structure for the given molecule is to be drawn.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has the higher priority. In 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

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Answer 25

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 the structure of (R)-2-bromohexane.

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