Tutorial sheet 8 (31/1/2020)

Topics to be discussed

Anomeric effect, Fischer projections, R and S nomenclature, conformationally mobile

systems, optical activity, specific activity

1. Draw the structure of D- Glucose, D-Fructose, L-Fructose and D-Mannose. All these
undergo formation of an osazone with phenylhydrazine (write this reaction to show
the formation for one of them). Which of these osazones have same melting point?

The Osazones formed by D-Glucose and D-Fructose have the same melting point (180-185°).

Answer: All hexoses in this question will have identical melting points. The melting
point along with other physical properties is identical for enantiomers.

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2. Assign all the asymmetric centers in the above carbohydrate structures as R or S.

(2R,3S,4R,5R) (3S,4R,5R) (3R,4S,5S) (2S,3S,4R,5R)

3. Draw the Fischer projection for the amino acid L-threonine. (Tutors have to draw the
side chain and the alpha amino acid. Specify that the configuration at side chain is R
and at alpha carbon is S).

4. Draw the structure of the following molecules:

(i) (R)-2-chloropentane (ii) (S)-3-chloro-2-methylpentane

(iii) (S)-2-bromo-2-phenylbutane (iv) (R)-2-bromo-2-chlorobutane

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 5. D-Ribose is optically active but its reduction product D-ribitol is not. Explain this
observation based on the structures.
Ans:
D-Ribitol is a meso compound. Hence, it is optically inactive. A plane of symmetry
passes through C3- carbon.

(2S,4R)