H. но OH HO HO- CH2OH

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL4: Proton (1h) Nmr Spectroscopy
Section: Chapter Questions
Problem 1CTQ
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Question

Draw both pyranose anomers of each aldohexose using a threedimensional
representation with a chair pyranose. Label each anomer as
α or β.

H.
но
OH
HO
HO-
CH2OH
Transcribed Image Text:H. но OH HO HO- CH2OH
Expert Solution
Step 1

The given structure is,

Chemistry homework question answer, step 1, image 1

 

Step 2

The Fischer projection of D-sugar is converted to Haworth projection.

In step 1, The formation of pyranose ring takes place by the attack of hydroxyl substituent at carbon fifth on carbonyl carbon.

In step 2, CH2OH is drawn above the ring in Haworth projection of D-pyranose.

In step 3, At carbon first position, the substituents CH2OH and OH are cis to one other in beta-form. So, they are drawn above the ring. The substituents CH2OH and OH are trans to one other in alpha-form. So, substituent OH is drawn below the ring.

In step 4, the substituents that are found in right side in Fischer projection are drawn below the ring in Haworth projection. The substituents that are found in left side in Fischer projection are drawn above ring in Haworth projection.

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