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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

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Section
BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 16.7, Problem 16.6P
Textbook Problem
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Hydrolysis of an acetal in aqueous acid gives an aldehyde or a ketone and two molecules of alcohol or one molecule of a diol. Draw the structural formulas for the products of hydrolysis of the following acetals in aqueous acid.

Chapter 16.7, Problem 16.6P, Hydrolysis of an acetal in aqueous acid gives an aldehyde or a ketone and two molecules of alcohol

(a)

Interpretation Introduction

Interpretation:

The structural formulas for the products of hydrolysis of the given acetal in aqueous acid has to be drawn.

Concept introduction:

Acetals are a group of organic compound that contain two alkoxy (-OR) groups on the same carbon atom.

Organic Chemistry, Chapter 16.7, Problem 16.6P , additional homework tip  1

Acetals can be hydrolysed by addition of dilute acid. The excess of water drives the equilibrium toward the formation of the ketone or aldehyde and two molecules of alcohol or one molecule of diol.

Explanation of Solution

Hydrolysis of an acetal in aqueous acid gives an aldehyde or ketone and two molecules of alcohol or a molecule of a diol.

The hydrolysis of given acetal in aqueous acid can be shown as follows,

(b)

Interpretation Introduction

Interpretation:

The structural formulas for the products of hydrolysis of the given acetal in aqueous acid has to be drawn.

Concept introduction:

Acetals are a group of organic compound that contain two alkoxy (-OR) groups on the same carbon atom.

Organic Chemistry, Chapter 16.7, Problem 16.6P , additional homework tip  2

Acetals can be hydrolysed by addition of dilute acid. The excess of water drives the equilibrium toward the formation of the ketone or aldehyde and two molecules of alcohol or one molecule of diol.

(c)

Interpretation Introduction

Interpretation:

The structural formulas for the products of hydrolysis of the given acetal in aqueous acid has to be drawn.

Concept introduction:

Acetals are a group of organic compound that contain two alkoxy (-OR) groups on the same carbon atom.

Organic Chemistry, Chapter 16.7, Problem 16.6P , additional homework tip  3

Acetals can be hydrolysed by addition of dilute acid. The excess of water drives the equilibrium toward the formation of the ketone or aldehyde and two molecules of alcohol or one molecule of diol.

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Chapter 16 Solutions

Organic Chemistry
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Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 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 - Complete the equations for these oxidations. (a)...Ch. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Complete the following reactions.Ch. 16 - Name each compound, showing stereochemistry where...Ch. 16 - Draw a structural formula for each compound. (a)...Ch. 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 - With organolithium and organomagnesium compounds,...Ch. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - The Wittig reaction can be used for the synthesis...Ch. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - It is possible to generate sulfur ylides in a...Ch. 16 - Propose a structural formula for compound D and...Ch. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Draw structural formulas for the hemiacetal and...Ch. 16 - Draw structural formulas for the products of...Ch. 16 - Propose a mechanism to account for the formation...Ch. 16 - Propose a mechanism for this acid-catalyzed...Ch. 16 - In Section 11.5, we saw that ethers, such as...Ch. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Which of these molecules will cyclize to give the...Ch. 16 - Draw a structural formula for the product of each...Ch. 16 - Following are structural formulas for amphetamine...Ch. 16 - Following is the final step in the synthesis of...Ch. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Draw a structural formula for the product formed...Ch. 16 - Draw a structural formula for the product of the...Ch. 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 - Disparlure is a sex attractant of the gypsy moth...Ch. 16 - Propose structural formulas for compounds A, B,...Ch. 16 - Following is a retrosynthetic scheme for the...Ch. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Propose a mechanism for this isomerization.Ch. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Following are the final steps in one industrial...Ch. 16 - Following is the structural formula of the...Ch. 16 - Both (S)-citronellal and isopulegol are naturally...Ch. 16 - At some point during the synthesis of a target...Ch. 16 - Both 1,2-diols and 1,3-diols can be protected by...Ch. 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 - As we saw in Chapter 6, carbon-carbon double bonds...Ch. 16 - Ribose, a carbohydrate with the formula shown,...Ch. 16 - The favorite nuclide used in positron emission...Ch. 16 - Use the reaction roadmap you made for Problem...Ch. 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 - Cetrizine is a nonsedating antihistamine. The...Ch. 16 - Wittig reactions are widely used in drug...Ch. 16 - Complete the following Wittig reactions.Ch. 16 - Complete the following Grignard reaction. The...

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