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Chapter 23: Q7. (page 1217)

Draw the Haworth projection for the cyclic structure of D-mannose by laying down the Fischer projection.

Short Answer

Expert verified

The Haworth projection for the cyclic structure of D-mannose is drawn below.

Haworth Projection

Step by step solution

01

Fisher Projection

Fischer projection depicts the three-dimensional structure of a molecule on a page, with horizontal lines representing bonds that extend above the plane of the paper, and vertical lines representing bonds that extend away from the viewer.

Fischer projection of D-mannose

02

Haworth Projection of D-mannose

In carbohydrates, closed cyclic structure of molecules is represented by Haworth projection. The distinction between the Fischer and Haworth projections is that the Fischer projection depicts the open chain structure whereas the Haworth projection depicts the closed cyclic structure.

Haworth Projection of D-mannose

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Most popular questions from this chapter

Use fig. 23-3 (the D-family of aldoses) to name the following aldoses.

(a) The C2 epimer of D-xylose

(b) The C3 epimer of D-erythrose

(c) The C3 epimer of D-altros

(d) The enantiomer of D-talose

(e) The C-5 epimer of D-idose

Draw the expected product of the reaction of the following sugars with excess methyl iodide and silver oxide.

  1. ฮฑ-D-fructofuranose
  2. ฮฒ-D-galactopyranose

Like glucose, galactose mutarotates when it dissolves in water. The specific rotation of ฮฑ-D-galactopyranoseis +150.70 , and that of the ฮฒ anomer is +52.80 . When either of the pure anomers dissolves in water, the specific rotation gradually changes to +80.20. Determine the percentages of the two anomers present at equilibrium.

Trehalose is a nonreducing disaccharide (C12H22O11) isolated from the poisonous mushroom Amanita muscaria. Treatment with an ฮฑ -glucosidase converts trehalose to two molecules of glucose, but no reaction occurs when trehalose is treated with a ฮฒ -glucosidase. When trehalose is methylated by dimethyl sulfate in mild base and then hydrolyzed, the only product is 2,3,4,6-tetra-O-methylglucose. Propose a complete structure and systematic name for trehalose.

Raffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose does not reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinose gives D-glucose, D-fructose, and D-galactose. When raffinose is treated with invertase, the products are D-fructose and a reducing disaccharide called melibiose. Raffinose is unaffected by treatment with a-galactosidase, but an ฮฑ -galactosidase hydrolyzes it to D-galactose and sucrose. When raffinose is treated with dimethyl sulfate and base followed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetra-O-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the complete structures of raffinose and melibiose and give a systematic name for melibiose.

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