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ChemistryOrganic Chemistry8th Edition
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Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. When D-ribose is treated with methanol in the presence of an acid catalyst, two cyclic acetals, A and B, are formed, both with molecular formula C 6 H 12 O 5 . These are separated, and each is treated with sodium periodate (Section 10.8C) followed by dilute aqueous acid. Both A and B yield the same three products in the same ratios. From this information, deduce whether the cyclic hemiacetal formed by D-ribose is four-membered, five-membered, or six-membered.

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Organic Chemistry

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

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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 16, Problem 16.70P
Textbook Problem
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Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. When D-ribose is treated with methanol in the presence of an acid catalyst, two cyclic acetals, A and B, are formed, both with molecular formula C6H12O5. These are separated, and each is treated with sodium periodate (Section 10.8C) followed by dilute aqueous acid. Both A and B yield the same three products in the same ratios.

Chapter 16, Problem 16.70P, Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could

From this information, deduce whether the cyclic hemiacetal formed by D-ribose is four-membered, five-membered, or six-membered.

Interpretation Introduction

Interpretation:

The given reaction is

Organic Chemistry, Chapter 16, Problem 16.70P

The cyclic hemiacetals formed from D-ribose are four-membered or five-membered or six-membered has to be given.

Concept Introduction:

Cyclic hemiacetals are formed by the intramolecular reaction of a carbonyl group with alcohol group.

Explanation of Solution

When D-ribose reacts with methanol, internal reaction occurs in D-ribose molecule between alcohol and aldehyde.  The reaction can be given as

Ribose is a five carbon compound...

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Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Show how these four products can be synthesized...Ch. 16.6 - Show how each alkene can be synthesized by a...Ch. 16.7 - Hydrolysis of an acetal in aqueous acid gives an...Ch. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Acid-catalyzed hydrolysis of an imine gives an...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. 16.8 - 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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