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Chapter 19: Q85E (page 648)

When glucose (Problem 19-52) is treated with\(NaB{H_4}\), reaction occurs to yield sorbitol, a polyalcohol commonly used as a food additive. Show how this reduction occurs.

Short Answer

Expert verified

Reduction followed as:

Step by step solution

01

Reduction with sodium borohydride

Sodium borohydride\(NaB{H_4}\)is the mild reducing agent which is used to reduce the aldehyde and ketone carbonyl group to the alcohol. It reduces aldehyde to primary alcohol and ketone to secondary alcohol it do not reduce the higher carbonyl like carboxylic acid and ether so, it is a mild reagent.

02

 Step 2: Reduction of glucose with sodium borohydride

As glucose contain the aldehyde group and sodium borohydride is the basic reducing agent so it abstracts the proton of the aldehyde followed by hydrolysis convert the carbonyl into the hydroxyl group as the primary alcohol is formed in sorbitol as shown below:

Reduction of Glucose

03

 Step 3: Reduction of glucose

Reduction of glucose to form sorbitol is followed by hydrolysis by converting the open aldehyde to alcohol group.

Compound Formation

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Most popular questions from this chapter

Draw structures corresponding to the following names:

  1. Bromoacetone
  2. (S)-2-Hydroxypropanal
  3. 2-Methyl-3-heptanone
  4. (2S,3R)-2,3,4-Trihydroxybutanal
  5. 2,2,4,4-Tetramethyl-3-pentanone
  6. 4-Methyl-3-penten-2-one
  7. Butanedial
  8. 3-Phenyl-2-propenal
  9. 6,6-Dimethyl-2,4-cyclohexadienone
  10. p-Nitroacetophenone

How might you use mass spectrometry to distinguish between the following pairs of isomers?

(a) 3-Methyl-2-hexanone and 4-methyl-2-hexanone

(b) 3-Heptanone and 4-heptanone

(c) 2-Methylpentanal and 3-methylpentanal

Name the following aldehydes and ketones:

The following molecular model represents a tetrahedral intermediateresulting from addition of a nucleophile to an aldehyde or ketone. Identifythe reactants, and write the structure of the final product when thenucleophilic addition reaction is complete.

The proton NMR spectrum for a compound with formula C10H12O2is shown below. The infrared spectrum has a strong band at. The broadband-decoupled 13CNMR spectral results are tabulated along with the DEPT-135 and DEPT-90 information. Draw the structure of this compound.
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