The natural ( − ) -menthol with 1 R , 2 S , 5 R - stereochemistry should be identified from the possible stereoisomers that exist for ( − ) -menthol . Concept introduction : ( − ) -menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of ( − ) -menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

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Answer 1

Question

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

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12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?

3. Deduce the relationship between each of the following pairs as enantiomers, cis-trans isomers, constitutional isomers or same molecule. (a) H and Br он но Br (b) OH OH OH H and OH

(a) How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.

Answer 2

Question

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

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Answer 3

Question

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

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Answer 4

Question

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

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Answer 5

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

Answer 6

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 7

Chapter 5, Problem 52P

(a)

Interpretation Introduction

Interpretation:The natural (−)-menthol with 1R,2S,5R- stereochemistry should be identified from the possible stereoisomers that exist for (−)-menthol .

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 8

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 9

(b)

Interpretation Introduction

Interpretation: The natural (+)-isomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 10

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 11

(c)

Interpretation Introduction

Interpretation: The natural (+)-neomenthol with 1S,2R,5R- stereochemistry should be identified.

Concept introduction: (−)-menthol is also known as laevo-menthol . It is naturally found in the aroma of peppermint and is used as essential oil. The structure of (−)-menthol has three chiral centers and hence total eight stereoisomers exist for menthol as illustrated below.

Answer 12

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

Answer 13

(c)

Interpretation Introduction

Interpretation: The stability order for the three diastereomers namely menthol, isomenthol, and neomenthol should be determined.

Concept introduction:In chair form all the C—C—C bond angle are 109.5 ° . Since this is ideal tetrahedral angle so there is no angular strain in chair form. The staggered C—H

bond further allows for no amount of torsional strain. There are two kinds of hydrogens in cyclohexane namely axial and equatorial indicated as follows:

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 5.1 - Prob. 5.3E Ch. 5.1 - Prob. 5.4E Ch. 5.1 - Prob. 5.5E Ch. 5.2 - Prob. 5.6E Ch. 5.2 - Prob. 5.8TIY Ch. 5.3 - Prob. 5.9E Ch. 5.3 - Prob. 5.11TIY Ch. 5.3 - Prob. 5.12E Ch. 5.4 - Prob. 5.13E Ch. 5.4 - Prob. 5.14E

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