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

Rank the following groups in order of decreasing priority. −C≡CH, −CH(CH3)2, −CH2CH3, −CH=CH2

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