Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 16.5, Problem 16.4P

(a)

Interpretation Introduction

Interpretation:

Show how the gicven product can be synthesized from the Grignard reagent.

Concept introduction:

Alkyl or aryl magnesium halides (RMgX) are known as Grignard reagent. The Grignard reaction is an organometallic chemical reaction in which the Grignard reagent act as nucleophile and attack electrophilic carbon atom that are present within polar bonds to yield a carbon-carbon bond.

Addition of a Grignard reagent to an aldehyde/ketone followed by protonation will produce an alcohol.

Thus,

Reaction of Grignard reagent with formaldehyde yields primary alcohol. Secondary and tertiary alcohol can be prepared by the reaction of Grignard reagent with any aldehyde (except formaldehyde) and ketone respectively.

An equimolar mixture of the two enantiomers is called racemic mixture and it is optically inactive.

(b)

Interpretation Introduction

Interpretation:

Show how the gicven product can be synthesized from the Grignard reagent.

Concept introduction:

Alkyl or aryl magnesium halides (RMgX) are known as Grignard reagent. The Grignard reaction is an organometallic chemical reaction in which the Grignard reagent act as nucleophile and attack electrophilic carbon atom that are present within polar bonds to yield a carbon-carbon bond.

Addition of a Grignard reagent to an aldehyde/ketone followed by protonation will produce an alcohol.

Thus,

Reaction of Grignard reagent with formaldehyde yields primary alcohol. Secondary and tertiary alcohol can be prepared by the reaction of Grignard reagent with any aldehyde (except formaldehyde) and ketone respectively.

An equimolar mixture of the two enantiomers is called racemic mixture and it is optically inactive.

(c)

Interpretation Introduction

Interpretation:

Show how the gicven product can be synthesized from the Grignard reagent.

Concept introduction:

Alkyl or aryl magnesium halides (RMgX) are known as Grignard reagent. The Grignard reaction is an organometallic chemical reaction in which the Grignard reagent act as nucleophile and attack electrophilic carbon atom that are present within polar bonds to yield a carbon-carbon bond.

Addition of a Grignard reagent to an aldehyde/ketone followed by protonation will produce an alcohol.

Thus,

Reaction of Grignard reagent with formaldehyde yields primary alcohol. Secondary and tertiary alcohol can be prepared by the reaction of Grignard reagent with any aldehyde (except formaldehyde) and ketone respectively.

An equimolar mixture of the two enantiomers is called racemic mixture and it is optically inactive.

(d)

Interpretation Introduction

Interpretation:

Show how the gicven product can be synthesized from the Grignard reagent.

Concept introduction:

Alkyl or aryl magnesium halides (RMgX) are known as Grignard reagent. The Grignard reaction is an organometallic chemical reaction in which the Grignard reagent act as nucleophile and attack electrophilic carbon atom that are present within polar bonds to yield a carbon-carbon bond.

Addition of a Grignard reagent to an aldehyde/ketone followed by protonation will produce an alcohol.

Thus,

Reaction of Grignard reagent with formaldehyde or oxirane yields primary alcohol. Secondary and tertiary alcohol can be prepared by the reaction of Grignard reagent with any aldehyde (except formaldehyde) and ketone respectively.

An equimolar mixture of the two enantiomers is called racemic mixture and it is optically inactive.

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Show how these four products can be synthesized from the same Grignard reagent.
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Chapter 16 Solutions

Organic Chemistry

Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
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