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Chapter 19: Q52E (page 648)

When crystals of pure 伪-glucose are dissolved in water, isomerization occurs slowly to produce 尾-glucose. Propose a mechanism for isomerization.

Short Answer

Expert verified

The Mutarotation is differ from specific rotation, due to the change in equilibrium between alpha and beta anomeric forms, in the aqueous solution.

Only those carbohydrates show mutarotation which is hemiacetal or hemiketal.

Step by step solution

01

Mutarotation

The Mutarotation is differ from specific rotation, due to the change in equilibrium between alpha and beta anomeric forms, in the aqueous solution.

Only those carbohydrates show mutarotation which is hemiacetal or hemiketal.

02

Mechanism for conversion of alpha glucose to beta glucose

In the first step lone pair of oxygen of hydroxyl get delocalized and the bond between carbon and oxygen gets a break. Further, the rotation of the bond is observed as shown in the following mechanism. In the next step negatively charge oxygen attacks the carbon and further rearrangement.

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Most popular questions from this chapter

The oxygen in water is primarily (99.8%) 16O, but water enriched with the heavy isotopeO18is also available. When an aldehyde or ketone is dissolvedinO18-enriched water, the isotopic label becomes incorporated into thecarbonyl group. Explain.

R2C=O+H2O鈬�R2C=O+H2Owhere O =O18

How would you carry out the following reactions? More than one step may be

required.

(a) 3-Hexyne3-Hexanone

(b) Benzenem-Bromoacetophenone

(c) BromobenzeneAcetophenone

(d) 1-Methylcyclohexene2-Methylcyclohexanone

Draw structures of compounds that fit the following descriptions:

  1. An 伪,尾-unsaturated ketone, C6H8O
  2. An 伪-diketone
  3. An aromatic ketone,C9H10O
  4. A diene aldehyde,C7H8O

Tamoxifen is a drug used in the treatment of breast cancer. How wouldyou prepare tamoxifen from benzene, the following ketone, and any other reagents needed?

Draw structures corresponding to the following names:

  1. Bromoacetone
  2. (S)-2-Hydroxypropanal
  3. 2-Methyl-3-heptanone
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  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
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