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Chapter 5: Q55 E. (page 148)

On reaction with hydrogen gas by a platinum catalyst, ribose (Problem 5-54) is converted into ribitol. Is ribitol optically active or inactive? Explain.

Short Answer

Expert verified

A ribitol is an optically inactive compound.

Step by step solution

01

Optically active compounds

Optical active compounds are those which are capable of rotating plane-polarized light.Meso compounds are optically inactive compounds. For a compound to be optically active, it must have a chiral center.

02

Find out if ribitol is optically active or inactive

On catalytic hydrogenation (), ribose containing aldehyde converts into a hydroxyl group. When the plane of symmetry is drawn inside the molecule so that two halves of ribitol become mirror images of one another, this resulting compound is meso compound and, hence, optically inactive.

Conversion of Ribose to Ribitol

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Most popular questions from this chapter

One of the steps in fat metabolism is the hydration of crotonate to yield 3-hydroxybutyrate. This reaction occurs by addition of 鈥揙H to the Si face at C3, followed by protonation at C2, also from the Si face. Draw the product of the reaction, showing the stereochemistry of each step.

Draw examples of the following:

(a) A meso compound with the formula

(b) A meso compound with the formula

(c) A compound with two chirality centers, one R and the other S

Which, if any, of the following structures represent meso compounds? (Blue = N, green = Cl.)

Cis-1,2-Dimethylcyclohexane is optically inactive even though it has two chirality centers. Explain.

Q 31 Which of the following objects are chiral?

(a) A basketball

(b) A fork

(c) A wine glass

(d) A golf club

(e) A spiral staircase

(f) A snowflake
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