Draw cyclic structures for D-ribose and D-mannose.

Short Answer

Expert verified
The cyclic structures of D-ribose and D-mannose can be obtained by converting their linear Fischer projections to Haworth projections. Form cyclic structures via intramolecular hemiacetal formation by reacting the carbonyl carbon (C-1) with the hydroxyl group at the last stereogenic carbon (C-4 in D-ribose and C-5 in D-mannose). After converting, draw both α and β anomers for D-ribose and D-mannose in the Haworth projection.

Step by step solution

01

Draw the Fischer projection of D-ribose and D-mannose#linear_structure#

First, let's draw the Fischer projection for D-ribose and D-mannose (linear structure). D-ribose is an aldopentose sugar, and D-mannose is an aldohexose sugar. To draw the Fischer projection, we need to represent the carbon chain in a vertical line and the hydroxyl groups (OH) at right angles according to the following orientations: For D-ribose: D-ribose - Carbon atoms: C-1 to C-5 C-1: The carbonyl group forming an aldehyde. C-2: OH on the right side. C-3: OH on the left side. C-4: OH on the right side. C-5: CH₂OH on the right side For D-mannose: D-mannose - Carbon atoms: C-1 to C-6 C-1: The carbonyl group forming an aldehyde. C-2: OH on the left side. C-3: OH on the right side. C-4: OH on the right side. C-5: OH on the left side. C-6: CH₂OH on the right side. Now we have the linear Fischer projections for both D-ribose and D-mannose.
02

Converting Fischer projection to Haworth projection (cyclic structure)#convert_structure#

Now, let's convert the Fischer projection to the Haworth projection, which better represents the cyclic structure. We'll form the cyclic structures through an intramolecular hemiacetal formation which requires a reaction between the carbonyl carbon (C-1) and the hydroxyl (OH) group at the last stereogenic carbon in the Fischer projection (C-4 in D-ribose and C-5 in D-mannose). For D-ribose: 1. Rotate the -OH group on C-4 upwards, forming a bond with the C-1 carbonyl (also rotate the CH₂OH group at C-5 upwards). 2. The C-1 carbonyl carbon forms a new stereocenter, creating an anomeric carbon (C-1) with two possible configurations: alpha (α) or beta (β). In the alpha configuration, the -OH of the newly formed anomeric carbon points down while the β configuration has the -OH pointing up. 3. Draw both α and β anomers of D-ribose in the Haworth projection. For D-mannose: 1. Rotate the -OH group on C-5 upwards, forming a bond with the C-1 carbonyl (also rotate the CH₂OH group at C-6 upwards). 2. The C-1 carbonyl carbon forms a new stereocenter, creating an anomeric carbon (C-1) with two possible configurations: alpha (α) or beta (β). In the alpha configuration, the -OH of the newly formed anomeric carbon points down while the β configuration has the -OH pointing up. 3. Draw both α and β anomers of D-mannose in the Haworth projection. Now we have cyclic structures for both D-ribose and D-mannose, in α and β anomeric configurations.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free