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Chapter 28: Question 28.58 (page 1149)

Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Step by step solution

01

Reactant

Reactants are starting material/substance/compound in the chemical reaction that takes part in the reaction which helps in the creation of the product.

It is always placed on the left side of the chemical reaction and reacts with the reagent to give products.

02

Formation of intermediate

When methyl-d-glucose is treated with benzaldehyde a compound is formed, then a base OH- attack to the compound removal of water molecule takes place which on protonation an intermediate is formed as shown below.

Formation of intermediate

03

Formation of methyl-4-6-O-benzylidene-d-glucose 

A water molecule is removed from the intermediate again OH- attack to the compound which forms methyl-4-6-O-benzylidene-d-glucose withH2O as a byproduct.

Formation of methyl-4-6-O-benzylidene-d-glucose

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Most popular questions from this chapter

Which aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) D-lyxose; (c) D-galactose?

What products are formed when each compound is subjected to a Kiliani–Fischer synthesis?

(a.)

(b.)

Consider the following six compounds (A-F).

How are the two compounds in each pair related? Choose from enantiomers, epimers, diastereomers but not epimers, constitutional isomers, and identical compounds.

  1. A and B
  2. A and C
  3. B and C
  4. A and D
  5. E and F

What two aldoses yield D-xylose on Wohl degradation?

A D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?

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