Smith6e Chapter27 TB AnswerKey

Organic Chemistry, 6e (Smith)
Chapter 27 Amino Acids and Proteins
1) Which of the following compounds is not an amino acid?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 1 Easy
Section: 27.01
Topic: Amino Acids, Peptides, and Proteins
Bloom's: 2. Understand
Chapter: 27
2) What is the configuration of naturally occurring amino acids?

A) D
B) S
C) L
D) R
Answer: C
Difficulty: 1 Easy
Section: 27.01
Bloom's: 1. Remember
Chapter: 27
Accessibility: Keyboard Navigation
1
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3) Which is the correct structure for serine?
A) A
B) B
C) C
D) D
Answer: C
Difficulty: 1 Easy
Section: 27.01
Chapter: 27
4) Which is the correct structure for the amino acid proline?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 1 Easy
Section: 27.01
Chapter: 27
2
5) Which is the correct structure for the amino acid cysteine?
A) A
B) B
C) C
D) D
Answer: D
Difficulty: 1 Easy
Section: 27.01
Chapter: 27
6) Which is the correct structure for the amino acid valine?
A) A
B) B
C) C
D) D
Answer: C
Difficulty: 1 Easy
Section: 27.01
Chapter: 27
3
7) Which of the following is the correct structure for alanine at pH = 7?
A) A
B) B
C) C
D) D
Answer: D
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
8) Which of the following is the correct structure for aspartic acid at pH = 1?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
4
9) Which of the following aldehydes would be a good starting material in the Strecker synthesis
of phenylalanine?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
10) What reagents would you use to convert acetaldehyde into alanine?
A) NH3
B) HCN
C) NaCN, NH4Cl
D) NaNH2
Answer: C
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
5
11) What is the separation of a racemic mixture into its component enantiomers called?
A) Diastereomers
B) Meso
C) Resolution
D) Neutralization
Answer: C
Difficulty: 1 Easy
Section: 27.03
Bloom's: 3. Apply
Chapter: 27
12) Why does the formation of salts of a racemic mixture of N-acetyl valine with a single
enantiomer of a-methylbenzylamine enable the separation of the two enantiomers of N-acetyl
valine?
A) They form amides.
B) They form diastereomers.
C) They form salts.
D) They form meso compounds.
Answer: B
Difficulty: 2 Medium
Section: 27.04
Bloom's: 3. Apply
Chapter: 27
13) Why can glycine not be resolved into two enantiomers?

A) It has no stereogenic centers.
B) It has no nitrogen atoms.
C) It has no aromatic rings.
D) It cannot be converted into a salt.
Answer: A
Section: 27.04
Bloom's: 3. Apply
Chapter: 27
6
14) What amino acid is at the N-terminus of the following peptide?
A) Valine
B) Serine
C) Alanine
D) Proline
Answer: A
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
15) What amino acid is at the C-terminus of the following peptide?
A) Valine
B) Serine
C) Alanine
D) Proline
Answer: C
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
7
16) Why is the s-trans form of an amide bond more stable?
A) There is no s-cis form in an amide bond.
B) The oxygen is hydrogen-bonded with the nitrogen atom.
C) The nitrogen is able to be sp2-hybridized.
D) The more sterically bulky groups are farther apart.
Answer: D
Difficulty: 1 Easy
Section: 27.06
Bloom's: 3. Apply
Chapter: 27
17) Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room temperature?
A) These amide bonds are not stable.
B) There is partial double bond character between the carbonyl carbon and the nitrogen atom.
C) The oxygen atom is hydrogen-bonded with the nitrogen atom.
D) The side-chains can form hydrogen bonds.
Answer: B
Difficulty: 1 Easy
Section: 27.06
Bloom's: 3. Apply
Chapter: 27
18) Which of the following is the major advantage of the Merrifield synthesis of peptides?
A) It allows for the formation of absolutely no by-products.
B) Impurities can be easily washed away.
C) Excess reagent can be used.
D) It prevents hydrogenation.
Answer: B
Difficulty: 1 Easy
Section: 27.07
Bloom's: 3. Apply
Chapter: 27
8
19) What are the basic steps in the Merrifield peptide synthesis?
A) Coupling and hydrolysis
B) Hydrolysis and deprotection
C) Deprotection and hydrogenation
D) Coupling and deprotection
Answer: D
Difficulty: 1 Easy
Section: 27.07
Bloom's: 3. Apply
Chapter: 27
20) Which of the following is the structure of the amino acid lysine?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
9
21) What is (are) the missing reagent(s) in the reaction below?
A) NH3
B) HCN
C) NaCN, NH4Cl
D) NaNH2
Answer: C
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
10
22) What is the major organic product for the following reaction?
A) A
B) B
C) C
D) D
Answer: A
Difficulty: 3 Hard
Section: 27.07
Bloom's: 3. Apply
Chapter: 27
11
23) What is the IUPAC or common name for the following compound?
A) Cysteinylalanine
B) Alanylcysteine
C) Serinylalanine
D) Alanylserine
Answer: B
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
24) Amino acid synthesis is possible by all except one of the pathways listed. Which is not a
synthetic pathway for amino acids?
A) Amination of malonic ester followed by hydrolysis and decarboxylation
B) Nucleophilic addition of NH3 to an aldehyde followed by addition of cyanide to the imine,
and, finally, hydrolysis
C) SN2 reaction using an a-halo carboxylic acid with ammonia as the nucleophile
D) Reaction of NH4Cl and NaCN with an aldehyde followed by an acidic work-up
Answer: A
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
12
25) Which of the following correctly describes a protein?
A) a dipeptide; two amino acids joined together by one amide bond
B) a tripeptide; three amino acids joined together by two amide bonds
C) a polymer of more than 40 amino acids joined together by amide bonds
D) a polypeptide of any number of amino acids joined together by amide bonds
Answer: C
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
26) Which of the following correctly describes a peptide bond?

A) a bond between sp3-hybridized atoms only
B) a bond usually found in the s-cis conformation
C) an amide bond
D) the result of the formation of the carbonyl group of one amino acid with a R-group from the
other amino acid
Answer: C
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
27) Which of the following correctly describes the Merrifield synthesis?

A) It uses a solid phase technique for the synthesis of peptides.
B) It uses DCC (dicyclohexylcarbodiimide) to form the amide bond in a peptide synthesis.
C) It uses BOC (tert-butoxycarbonyl) as a protecting group for peptide synthesis.
D) It uses aqueous phase techniques for the synthesis of large polypeptides.
Answer: A
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
13
28) Which of the following correctly describes the tertiary structure of a peptide?
A) the three-dimensional conformations of localized regions of a protein
B) the particular sequence of amino acids that are joined together by peptide bonds
C) the structure is defined by the b-pleated sheet form
D) the three-dimensional shape adopted by the entire peptide
Answer: D
Difficulty: 1 Easy
Section: 27.05
Bloom's: 3. Apply
Chapter: 27
29) What are the only covalent bonds that stabilize the tertiary structure of a peptide?
A) Hydrogen bonds
B) Disulfide bonds
C) Van der Waal bonds
D) Ionic bonds
Answer: B
Difficulty: 1 Easy
Section: 27.07
Bloom's: 3. Apply
Chapter: 27
30) Which of the following is (are) globular protein(s)?

A) Hemoglobin
B) Keratins
C) Collagens
D) Elastins
Answer: A
Difficulty: 1 Easy
Section: 27.10
Chapter: 27
14
31) Which of the following is (are) fibrous protein(s)?
A) Keratins
B) Hormones
C) Enzymes
D) Antibodies
Answer: A
Difficulty: 1 Easy
Section: 27.10
Chapter: 27
32) What is the appropriate sequence of reaction conditions used to synthesize valine from
acetamidomalonic ester?
A) (1) NaOH; (2) (CH3)2CHBr; (3) Cl2, H2O, heat

B) (1) NaOCH2CH3; (2) (CH3)2CH2CHBr; (3) HCl, H2O, heat
C) (1) NaOCH2CH3; (2) (CH3)2CHBr; (3) HCl, H2O, heat
D) (1) NaOH; (2) CH3CH2CH2Br; (3) HCl, H2O, heat
Answer: C
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
15
33) Below is a 2D chromatogram that shows the separation of five amino acids. In this
technique, the amino acid mixture is first separated by chromatography using a polar solvent
system. Then the plate is rotated 90°, and the amino acids are further separated by
electrophoresis. Identify the spots obtained from a mixture of Trp, Glu, Lys, Ile and Thr. A table
with isoelectric points is included to aid in solving this problem.
amino acid-pI value

Trp-5.9
Glu-3.2
Lys-9.7
Ile-6.0
Thr-5.6
A) 1=Lys, 2=Thr, 3=Glu, 4=Trp, 5=Ile

B) 1=Glu, 2=Thr, 3=Lys, 4=Trp, 5=Ile
C) 1=Lys, 2=Ile, 3=Glu, 4=Trp, 5=Thr
D) 1=Glu, 2=Ile, 3=Lys, 4=Trp, 5=Thr
Answer: A
Difficulty: 3 Hard
Section: 27.03
Bloom's: 3. Apply
Chapter: 27
16
34) Below is a proposed method for resolving a racemic mixture of (R)- and (S)-phenylalanine.
Upon separation of the products, will this method produce (R)- or (S)-phenylalanine?
A) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-amino acids.
B) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of L-amino acids.
C) (R)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-amino
acids.
D) (S)-Phenylalanine is produced since the acylase only hydrolyzes the amides of D-amino acids.
Answer: B
Section: 27.03
Bloom's: 3. Apply
Chapter: 27
35) Give the order (1st to last) in which the following amino acids would be eluted with a buffer
of pH = 4 from a column containing a cationic-exchange resin (Dowex 50): Arg (pI = 10.8), Ser
(pI = 5.7), Asp (pI = 2.8) and His (pI = 7.6).
A) His, Ser, Asp, Arg
B) Arg, His, Ser, Asp
C) His, Ser, Arg, Asp
D) Asp, Ser, His, Arg
Answer: D
Difficulty: 3 Hard
Section: 27.03
Bloom's: 3. Apply
Chapter: 27
17
36) Reaction of a polypeptide, composed of 12 amino acids, with carboxypeptidase A releases
Met (C-terminal amino acid). The polypeptide undergoes partial hydrolysis to give 12 groups of
peptides. Use the groups of overlapping amino acids to determine the proper sequence of this
polypeptide. Note: Since these lists of peptides are separated by commas, they are not necessarily
in the proper sequence.
Ser, Lys, Trp-5. Met, Ala, Gly- 9. Lys, Ser

Gly, His, Ala-6. Ser, Lys, Val -10. Glu, His, Val
Glu, Val, Ser-7. Glu, His-11. Trp, Leu, Glu
Leu, Glu, Ser-8. Leu, Lys, Trp-12. Ala, Met
A) Met-Ala-Gly-His-Glu-Val-Ser-Lys-Trp-Leu-Glu-Ser
B) Met-Ala-Gly-Glu-His-Ser-Val-Lys-Trp-Leu-Glu-Ser
C) Ser-Glu-Leu-Trp-Lys-Ser-Val-Glu-His-Gly-Ala-Met
D) Ser-Lys-Leu-Trp-Lys-Ser-Val-His-Glu-Gly-Ala-Met
Answer: C
Difficulty: 3 Hard
Section: 27.03
Bloom's: 3. Apply
Chapter: 27
37) What is formed by the combination of four amino acids?

A) A protein
B) A polypeptide
C) A tripeptide
D) A tetrapeptide
Answer: D
Difficulty: 1 Easy
Section: 27.06
Bloom's: 3. Apply
Chapter: 27
18
38) Which of the following amino acids is achiral?
A) Phenylalanine
B) Glycine
C) Valine
D) Alanine
Answer: B
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
39) Which of the following amino acids does not have an L-isomer?
A) Alanine
B) Valine
C) Glycine
D) Leucine
Answer: C
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
40) Which one of the following naturally occurring amino acids does not have an S
configuration?
A) Cysteine
B) Alanine
C) Tyrosine
D) Isoleucine
Answer: A
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
19
41) What is the name given to the pH at which the concentration of the zwitterionic form of an
amino acid is at a maximum concentration?
A) Electric point
B) Dipolar point
C) Neutral point
D) Isoelectric point
Answer: D
Difficulty: 1 Easy
Section: 27.01
Bloom's: 3. Apply
Chapter: 27
42) What is the major organic product for the following reaction?
A) I
B) II
C) III
D) IV
Answer: A
Section: 27.07
Bloom's: 3. Apply
Chapter: 27
20
43) What is the product of the following reaction? (Assume workup to neutralize.)
A) I
B) II
C) III
D) IV
Answer: A
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
21
A) I
B) II
C) III
D) IV
Answer: B
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
22
A) I
B) II
C) III
D) IV
Answer: C
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
23
A) I
B) II
C) III
D) IV
Answer: D
Difficulty: 1 Easy
Section: 27.02
Bloom's: 3. Apply
Chapter: 27
24

Smith6e Chapter27 TB AnswerKey

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Smith6e Chapter27 TB AnswerKey

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Organic Chemistry, 6e (Smith)

Chapter 27 Amino Acids and Proteins

1) Which of the following compounds is not an amino acid?

2) What is the configuration of naturally occurring amino acids?

4) Which is the correct structure for the amino acid proline?

6) Which is the correct structure for the amino acid valine?

8) Which of the following is the correct structure for aspartic acid at pH = 1?

13) Why can glycine not be resolved into two enantiomers?

15) What amino acid is at the C-terminus of the following peptide?

26) Which of the following correctly describes a peptide bond?

27) Which of the following correctly describes the Merrifield synthesis?

30) Which of the following is (are) globular protein(s)?

A) (1) NaOH; (2) (CH3)2CHBr; (3) Cl2, H2O, heat

amino acid-pI value

A) 1=Lys, 2=Thr, 3=Glu, 4=Trp, 5=Ile

Ser, Lys, Trp-5. Met, Ala, Gly- 9. Lys, Ser

37) What is formed by the combination of four amino acids?

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