Q. 13.70 - An Introduction to General, Organic, and Biological Chemistry

Question

Use the Fischer projection for D-gulose in problem $13.69$ to answer each of the following: $(13.3,13.5)$

a. Draw the Fischer projection and name the product formed by the reduction of D-gulose.

b. Draw the Fischer projection and name the product formed by the oxidation of D-gulose.

Step-by-Step Solution

Answer

• Glucose has six carbon atoms, it is classified as a hexose monosaccharide. 

a)

             

b)

                                        

Step 1: Introduction (Part a)

• An aldehyde functional group is present on one of the carbon atoms. 
• As a result, it belongs to the aldohexose group. 
• It can be dextro- (as in D-glucose) or laevo- (as in L-glucose) depending on the location of the hydroxyl (-OH) groups (as in L-glucose). 
• When rotating plane polarised light clockwise, this nomenclature based on Fischer projection denotes D–. L– is the counterclockwise rotation of plane polarised light. 

Step 2 a : Draw the Fischer projection and name the product formed by the reduction of D-gulose.

Oxidation of D-glucose gives D-sorbital when aldehyde of glucose reduces into alcohol

Step 3 :b Draw the Fischer projection and name the product formed by the oxidation of D-gulose.

In oxidation of glucose aldehyde part oxidizes into carboxylic acid and product is glucuronic acid