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Chapter 22: Problem 110

Why is glycine not optically active?

Short Answer

Expert verified
Glycine is not optically active because its alpha-carbon does not have four different substituents attached to it. The alpha-carbon in glycine is connected to an amino group (NH2), a carboxyl group (COOH), and two hydrogen atoms. Since it has two identical hydrogen atoms, it is not an asymmetric carbon atom, making glycine achiral and not optically active.

Step by step solution

01

Understand Glycine's Structure

To determine if glycine is optically active, we need to examine its structure. The chemical formula for glycine is NH2CH2COOH. In more detail, the structure can be represented as: H | H2N - C - COOH | H
02

Identify Asymmetric Carbon Atoms

An asymmetric carbon atom, or chiral center, is a carbon atom that has four different substituents attached to it. In the case of glycine, the carbon in question (which is the alpha-carbon) is connected to an amino group (NH2), a carboxyl group (COOH), and two hydrogen atoms.
03

Determine Optical Activity

Since the alpha-carbon is attached to two identical hydrogen atoms, it does not have four different substituents, and therefore, it is not an asymmetric carbon atom. Consequently, glycine does not have a chiral center, which means it is achiral and not optically active.

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Most popular questions from this chapter

All amino acids have at least two functional groups with acidic or basic properties. In alanine, the carboxylic acid group has $K_{a}=4.5 \times 10^{-3}\( and the amino group has \)K_{b}=7.4 \times 10^{-5} .$ Three ions of alanine are possible when alanine is dissolved in water. Which of these ions would predominate in a solution with \(\left[\mathrm{H}^{+}\right]=1.0 M ?\) In a solution with \(\left[\mathrm{OH}^{-}\right]=1.0 \mathrm{M} ?\)

In glycine, the carboxylic acid group has \(K_{a}=4.3 \times 10^{-3}\) and the amino group has \(K_{b}=6.0 \times 10^{-5} .\) Use these equilibrium constant values to calculate the equilibrium constants for the following. $$ \mathrm{a} .^{+} \mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{3} \mathrm{O}^{+} $$ $$ \mathrm{b} . \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H}+\mathrm{OH}^{-} $$ $$ \mathrm{c} .^{+} \mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H} \rightleftharpoons 2 \mathrm{H}^{+}+\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-} $$

In general terms, what does the tertiary structure of a protein represent? Distinguish between the secondary and tertiary structures of a protein.

How many different pentapeptides can be formed using five different amino acids?

Name all of the alcohols that have the formula $\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\( . How many ethers have the formula \)\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O} ?$
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