(a) Interpretation: The structure of a five carbon alkyne that contains a ring is to be stated. Concept introduction: The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is C n H 2 n − 2 . The name of the alkyne compounds ends with suffix − y n e . Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula C n H 2 n .

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Answer 1

Question

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

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Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.

Give reasons for the following: (i) p-nitrophenol is more acidic than p-methylphenol. (ii) Bond length of C—O bond in phenol is shorter than that in methanol. (iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.

Compound X (C4H9Br) reacts by heating with NaOH in H2O to form Y. The compound Y then undergoes acid catalysed hydration by H2SO4 in 180°C to form 2-methyl prop-1-ene. (e) Determine the structure of X and Y. (f) Predict a MAJOR product when compound Y reacts with H2SO4 in 140°C. (g) Draw a structural isomer of X. Name the isomer using IUPAC nomenclature. (h) Describe a chemical test to distinguish between compound Y and 1-butanol.

Answer 2

Question

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

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Answer 3

Question

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

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Answer 4

Question

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

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Answer 5

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

Answer 6

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Answer 7

Chapter 14, Problem 14.29AP

Interpretation Introduction

(a)

Interpretation:

The structure of a five carbon alkyne that contains a ring is to be stated.

Concept introduction:

The alkynes consist of a triple bond between two carbon atoms. The general formula of alkynes is CnH2n−2. The name of the alkyne compounds ends with suffix −yne. Hydrocarbons can also exist in ring like structures. The saturated rings have the general formula CnH2n.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure of a chiral alkyne that consists of six carbons is to be stated.

Concept introduction:

Chirality is a geometric property of molecules. Any molecule having a non-super imposable mirror image is said to be a chiral molecule. The basic requirement of chirality is the presence of an asymmetric carbon. This asymmetric carbon is known as the chiral centre. An asymmetric carbon is the one in which all the substituent are different.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The structure of a symmetrical alkyne that consists of six carbons and gives the same product on hydroboration oxidation or acid catalyzed hydration is to be stated.

Concept introduction:

Hydroboration oxidation of alkyne is the addition of water molecule to an alkyne group by Anti-Markovnikov addition. Anti-Markovnikov addition is when the hydrogen atom is attached to the carbon atom having less number of hydrogen.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The structure of a six carbon alkyne that can exist as diastereomers is to be stated.

Concept introduction:

Diastereomers are a type of stereoisomers. In diastereomers, the configurations of carbon atoms are different at one or more than one positions but not at all carbons. They are different from enantiomers as the enantiomers have configurations of all carbon atoms different. Diastereomers have different physical and chemical properties.

Answer 14

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Answer 16

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Answer 17

Ch. 14 - Prob. 14.1P Ch. 14 - Prob. 14.2P Ch. 14 - Prob. 14.3P Ch. 14 - Prob. 14.4P Ch. 14 - Prob. 14.5P Ch. 14 - Prob. 14.6P Ch. 14 - Prob. 14.7P Ch. 14 - Prob. 14.8P Ch. 14 - Prob. 14.9P Ch. 14 - Prob. 14.10P

Solution Summary: The author explains the structure of a chiral alkyne that consists of six carbons.

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