a) Interpretation: The ranking of the substituent is to done from the following sets of substituent. Concept introduction: Rule 1: a) Higher atomic number precedes lower. b) An atom node duplicated closer to the root ranks higher than one duplicated further. Rule 2: Higher atomic mass number precedes lower. Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds. Rule 4: a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst). b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs. c) r precedes s . Rule 5: An atom or group with descriptor R has priority over its enantiomorph S .

Question

Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

Answer 1

Question

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

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Answer 2

Question

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

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Answer 3

Question

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

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Answer 4

Question

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

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Answer 5

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 6

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 7

Chapter 5.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 8

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 9

Interpretation Introduction

b)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 10

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 11

Interpretation Introduction

c)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 12

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 13

Interpretation Introduction

d)

Interpretation:

The ranking of the substituent is to done from the following sets of substituent.

Concept introduction:

Rule 1:

a) Higher atomic number precedes lower.

b) An atom node duplicated closer to the root ranks higher than one duplicated further.

Rule 2: Higher atomic mass number precedes lower.

Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.

Rule 4:

a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).

b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.

c) r precedes s.

Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.

Answer 14

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Answer 25

Ch. 5.2 - Prob. 1P Ch. 5.2 - Prob. 2P Ch. 5.2 - Prob. 3P Ch. 5.2 - Prob. 4P Ch. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6P Ch. 5.5 - Prob. 7P Ch. 5.5 - Prob. 8P Ch. 5.5 - Prob. 9P Ch. 5.5 - Assign R or S configuration to the chirality...

Solution Summary: The author explains the Cahn-Ingold rules for assigning R and S configuration to the following molecules.

Chapter 5 Solutions