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Chapter 24: Problem 25

Which of the following amino acids are chiral: (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (b) \(\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (c) \(\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH} ?\)

Short Answer

Expert verified
Amino acids (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) and (c) \(\mathrm{CH}_{2}\left(\mathrm{OH}\right) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) are chiral while (b) \(\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) is not chiral.

Step by step solution

01

Identifying Chirality of Amino Acid (a)

Look at the structure of the given amino acid (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\). Find a carbon atom that is bonded to four different atoms or groups of atoms. This is the second carbon atom from the left in the given formula that is attached to a \(\mathrm{CH}_{3}\), an \(H\), a \(\mathrm{NH}_{2}\) and a \(\mathrm{COOH}\) group. Since it is bonded to four different groups, this amino acid is chiral.
02

Identifying Chirality of Amino Acid (b)

Focus on the given amino acid (b) \(\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\). Notice that there isn't any carbon atom bonded to four different groups, which means it's not chiral. Therefore this amino acid is not chiral.
03

Identifying Chirality of Amino Acid (c)

Take a look at the provided amino acid (c) \(\mathrm{CH}_{2}\left(\mathrm{OH}\right) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\). The carbon atom that is bonded to \(\mathrm{CH}_{2}\), \(\mathrm{OH}\), \(\mathrm{NH}_{2}\) and \(\mathrm{COOH}\) groups is the second one from the right. As it's bonded to four different groups, this amino acid is also chiral.

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Most popular questions from this chapter

Give the chemical names of the following organic compounds and write their formulas: marsh gas, grain alcohol, wood alcohol, rubbing alcohol, antifreeze, mothballs, chief ingredient of vinegar.

Name the classes to which the following compounds belong: (a) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CHO}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) (e) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

Give three sources of methane.

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