Question
Asked Mar 4, 2020
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Draw a stepwise mechanism for the following reaction.

ОН
Н
(2 equiv)
H*
HO..
ОН
НО
НО
Он
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ОН Н (2 equiv) H* HO.. ОН НО НО Он

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Expert Answer

Step 1

To form the target molecule, the conversion of pyranose into furanose takes place. The mechanism of the reaction is preceded by the protonation of the starting material, followed by shifting of electrons present on hydroxyl group to stabilize oxonium ion. In the next step, a hydroxyl group attached to fourth carbon attacks on the first carbon atom to generate furanose ring with a positive charge on -O atom followed by reaction with A- base to form furanose ring. The stepwise mechanism for the conversion of pyranose into furanose is shown below:

Chemistry homework question answer, step 1, image 1

Step 2

The [1] step of the reaction comprises the protonation of the carbonyl compound to produce alcohol. The hydroxyl group is attached to the electron deficient carbon atom. The corresponding reaction is shown below:

Chemistry homework question answer, step 2, image 1

Step 3

In [2] step, the electrons present on -OH group of furanose attacks on electron-deficient carbon atom of an alcohol, followed by [3] step in which abstraction of H+ ion by water takes place to form a hemiacetal. The corresponding reactions are shown b...

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