Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 7, Problem 46P

(a)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Acid Catalysed addition of water: When water is added to alkyne in the presence of an acid, the product formed will be an enol.  Enol contains a double bond and an OH group.  The OH group is bonded to one of the sp2 carbons.

If a carbonyl group is bonded to two alkyl groups, it is called as a ketone.  The enol formed in the acid catalysed addition of water will be easily converted into a ketone.

Conversion of terminal alkynes into enol: If we want to convert terminal alkyne into an enol, the presence of mercuric ion as a catalyst should be needed and the catalyst will increase the rate of the reaction.

Organic Chemistry (8th Edition), Chapter 7, Problem 46P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

NaNH2 will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

Pd/C: Hydrogenation can done using this catalyst and converts alkenes to alkanes.  The addition will be a syn addition.

(c)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

NaNH2 will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

Pd/C: Hydrogenation can done using this catalyst and converts alkenes to alkanes.  The addition will be a syn addition.

Acid Catalysed addition of water: When water is added to alkyne in the presence of an acid, the product formed will be an enol.  Enol contains a double bond and an OH group. The OH group is bonded to one of the sp2 carbons.

If a carbonyl group is bonded to two alkyl groups, it is called as a ketone.  The enol formed in the acid catalysed addition of water will be easily converted into a ketone.

Conversion of terminal alkynes into enol: If we want to convert terminal alkyne into an enol, the presence of mercuric ion as a catalyst should be needed and the catalyst will increase the rate of the reaction.

Organic Chemistry (8th Edition), Chapter 7, Problem 46P , additional homework tip  2

(d)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

NaNH2 will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

Pd/C: Hydrogenation can done using this catalyst and converts alkenes to alkanes.  The addition will be a syn addition.

(e)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

NaNH2 will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

Pd/C: Hydrogenation can done using this catalyst and converts alkenes to alkanes.  The addition will be a syn addition.

(f)

Interpretation Introduction

Interpretation:

The preparation method for the given compound has to be given by taking ethyne as starting material.

Concept Introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Different reagents are used for the deprotonation and one of the common reagent is sodium amide.

NaNH2 will deprotonate alkynes, alcohols and as a strong base it will deprotonate alkynes and produces acetylide ion.

Lindlar catalyst: The catalyst is used for the hydrogenation of alkynes in a syn manner.  This means both hydrogen are added on the same side across the triple bond and the product obtained will be a cis product.

Sodium in liquid ammonia: The catalyst is used for the formation of trans alkenes from alkynes.  Because of its more reactivity towards triple bonds, the reaction will stop at the formation of alkenes.

Pd/C: Hydrogenation can done using this catalyst and converts alkenes to alkanes.  The addition will be a syn addition.

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Chapter 7 Solutions

Organic Chemistry (8th Edition)

Ch. 7.6 - Prob. 12PCh. 7.6 - Prob. 13PCh. 7.7 - Prob. 14PCh. 7.7 - Which alkyne should be used for the synthesis of...Ch. 7.7 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.8 - Only one alkyne forms an aldehyde when it...Ch. 7.9 - Describe the alkyne you should start with and the...Ch. 7.9 - Prob. 20PCh. 7.10 - Prob. 21PCh. 7.10 - Prob. 22PCh. 7.10 - Prob. 23PCh. 7.10 - Rank the following from strongest base to weakest...Ch. 7.10 - Prob. 26PCh. 7.12 - Prob. 28PCh. 7 - What is the major product obtained from the...Ch. 7 - Draw a condensed structure for each of the...Ch. 7 - A student was given the structural formula of...Ch. 7 - Prob. 32PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 35PCh. 7 - Draw the mechanism for the following reaction:Ch. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 44PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 46PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What is each compounds systematic name?Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 7 - Prob. 50PCh. 7 - Draw the keto tautomer for each of the following:Ch. 7 - Show how each of the following compounds can be...Ch. 7 - A chemist is planning to synthesize 3-octyne by...Ch. 7 - Prob. 54PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 56PCh. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Show how the following compound can be prepared...Ch. 7 - Prob. 60P
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