Organic Chemistry A Short Course 13Th Ed By Hart Test Bank

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Organic Chemistry A Short Course 13Th Ed By Hart Test Bank

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WITH ANSWERS
Organic Chemistry A Short Course 13Th Ed By Hart Test Bank

Chapter 5 Stereoisomerism

 

MULTIPLE CHOICE

 

  1. Which of the following objects is chiral?
A) egg
B) pencil
C) cross country skis
D) paperclip
E) shoes

 

 

ANS:  E                    TOP:   Definitions

 

  1. Chiral molecules that have nonsuperimposable mirror images are called:
A) enantiomers
B) diastereomers
C) meso compounds
D) stereogenic
E) symmetrical

 

 

ANS:  A                    TOP:   Definitions

 

  1. Which of the following molecules has a mirror plane of symmetry?
 

 

 

A) 1
B) 2
C) 3
D) 4
E) all of them

 

 

ANS:  B                    TOP:   Definitions

 

  1. What is the process that separates enantiomers?
A) separation
B) decoupling
C) resetting
D) resolution
E) selective binding

 

 

ANS:  D                    TOP:   Definitions

 

  1. A 50:50 mixture of enantiomers
A) is a meso form.
B) is a pair of diastereomers.
C) is a racemic mixture.
D) rotates plane polarized light.
E) is a pair of conformers.

 

 

ANS:  C                    TOP:   Definitions

 

  1. The terms that best describe the isomeric relationship between staggered and eclipsed ethane are
A) configurational, achiral, diastereomers.
B) conformational, chiral, enantiomers.
C) conformational, achiral, diastereomers.
D) configurational, chiral, enantiomers.
E) conformational, achiral, enantiomers.

 

 

ANS:  C                    TOP:   Definitions

 

  1. Which of the molecules below has a stereogenic carbon atom?
 

 

 

A) 1
B) 2
C) 3
D) 2 and 3
E) 1, 2, and 3

 

 

ANS:  B                    TOP:   Definitions

 

  1. How many stereogenic centers are present in the following molecule?
 

 

 

A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  B                    TOP:   Definitions

 

  1. How many stereogenic centers are present in the following molecule?
 

 

A) 1
B) 2
C) 4
D) 6
E) 8

 

 

ANS:  B                    TOP:   Definitions

 

  1. How many chiral stereoisomers can be drawn for CH3CHClCHBrCH3?
A) 1
B) 2
C) 3
D) 4
E) 8

 

 

ANS:  D                    TOP:   Definitions

 

  1. How many stereogenic carbons are in the following molecule?
 

 

 

A) 0
B) 1
C) 2
D) 3
E) 4

 

 

ANS:  A                    TOP:   Definitions

 

  1. How many stereoisomers can be obtained from the monobromination of pentane?
A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  B                    TOP:   Definitions

 

  1. How many stereoisomers with the formula CH3CHICHICH3 are possible?
A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  C                    TOP:   Definitions

 

  1. The number of stereogenic centers in progesterone is:

progesterone (no stereochemistry shown)

A) 2
B) 3
C) 4
D) 5
E) 6

 

 

ANS:  E                    TOP:   Definitions

 

  1. The total number of possible stereoisomers of  is:

 

A) 2
B) 4
C) 6
D) 8
E) 0

 

 

ANS:  D                    TOP:   Definitions

 

  1. The total number of possible stereoisomers of 1-bromo-2-chlorocyclopentane is:
A) 2
B) 4
C) 6
D) 8
E) 0

 

 

ANS:  B                    TOP:   Definitions

 

  1. An unknown sample is tested with a polarimeter for optical activity.  The results of the test required no movement of the analyzer.  What samples would give this result?
A) pure enantiomer
B) meso compound
C) racemic mixture
D) both B and C
E) none of these

 

 

ANS:  D                    TOP:   Optical Activity

 

  1. An unknown sample is tested with a polarimeter for optical activity. The results of the test require movement of the analyzer. What samples would give this result?
A) pure enantiomer
B) meso compound
C) racemic mixture
D) both B and C
E) none of these

 

 

ANS:  A                    TOP:   Optical Activity

 

  1. Which of the following statements about enantiomers is INCORRECT?
A) they cannot be differentiated by spectra
B) they have the same melting and boiling points
C) the mirror image of the R enantiomer is the S enantiomer
D) the specific rotation of enantiomers has the same magnitude
E) without exception, S enantiomers will rotate plane-polarized light to the left (counterclockwise)

 

 

ANS:  E                    TOP:   Optical Activity

 

  1. The observed rotation for 100 mL of an aqueous solution containing 1 g of sucrose, placed in a 2-decimeter sample tube, is +1.33 at 25C.  What is the specific rotation of sucrose?
A) +66.5
B) +266
C) +41.5
D) +133
E) 108

 

 

ANS:  A                    TOP:   Optical Activity

 

  1. Which of the following molecules are the same?
 

 

 

A) 1 and 2
B) 3 and 4
C) 1 and 3
D) 2 and 3
E) 2 and 4

 

 

ANS:  C                    TOP:   Relationships Between Stereoisomers

 

  1. Which of the three molecules below is the enantiomer of the following molecule?
 

 

 

 

 

 

A) I
B) II
C) III
D) there are no enantiomers
E) both II and III

 

 

ANS:  A                    TOP:   Relationships Between Stereoisomers

 

  1. Which of the three molecules below is a diastereomer of the following molecule?
 

 

 

 

 

 

A) I
B) II
C) III
D) there are no diastereomers
E) both I and II

 

 

ANS:  C                    TOP:   Relationships Between Stereoisomers

 

  1. Which of the following are achiral conformers?
A) staggered and eclipsed forms of ethane
B) cis and trans-2-butene
C) meso and (2R,3R)-2,3-dibromobutane
D) (R) and (S)-lactic acid

 

 

ANS:  A                    TOP:   Relationships Between Stereoisomers

 

  1. Which of the following would constitute a pair of enantiomers?
A) staggered and eclipsed forms of ethane
B) cis and trans-2-butene
C) meso and (2R,3R)-2,3-dibromobutane
D) (2R,3R) and (2S,3S)-tartaric acid
E) none of these

 

 

ANS:  D                    TOP:   Relationships Between Stereoisomers

 

  1. The terms that best describe the relationship between (2R,3S)-2,3-butanediol and (2S,3S)-2,3-butanediol are
A) configurational, diastereomers.
B) conformational, enantiomers.
C) conformational, diastereomers
D) configurational, enantiomers.
E) configurational, cis/trans.

 

 

ANS:  A                    TOP:   Relationships Between Stereoisomers

 

  1. The terms that best describe the relationship between (2R,3S)-2-bromo-3-chlorobutane and (2S,3R)-2-bromo-3-chlorobutane are
A) configurational, achiral, diastereomers.
B) conformational, chiral, diastereomers.
C) configurational, chiral, enantiomers.
D) conformational, chiral, enantiomers.
E) configurational, chiral, diastereomers.

 

 

ANS:  C                    TOP:   Relationships Between Stereoisomers

 

  1. Which of the following statements about the pair of molecules shown below is not true?
 

 

 

A) They have the same boiling point.
B) One rotates plane polarized light in the opposite direction from the other.
C) They have the same density.
D) One rotates plane polarized light a different number of degrees than the other.
E) They are mirror images of each other.

 

 

ANS:  D                    TOP:   Relationships Between Stereoisomers

 

  1. According to the R-S convention, which priority is correct for the following sets of groups?
A) NH2 > Cl > CH3 > H
B) Cl > NH2 > CH3 > H
C) Cl > CH3 > NH2 > H
D) H > Cl > CH> NH2
E) CH3 > NH2 > Cl > H

 

 

ANS:  B                    TOP:   The R-S and E-Z Conventions

 

  1. (R)-2-chlorobutane is correctly represented by which of the following:
 

 

 

 

 

A) I
B) II
C) III
D) IV
E) V

 

 

ANS:  B                    TOP:   The R-S and E-Z Conventions

 

  1. Which of the following groups has the highest priority for assigning R-S absolute configuration?
A) CH2=CH
B) (CH3)2CH
C) (CH3)3C
D) CH3CH2
E) CH3

 

 

ANS:  C                    TOP:   The R-S and E-Z Conventions

 

  1. The correct IUPAC name for the following molecule is:
 

 

A) (E)-2-bromo-3-chloro-5-methyl-2-hexene
B) (E)-2-bromo-3-chloro-5-methyl-3-hexene
C) (Z)-2-bromo-3-chloro-5-methyl-3-hexene
D) (Z)-2-bromo-3-chloro-5-methyl-2-hexene
E) (E)-5-bromo-4-chloro-2-methyl-4-hexene

 

 

ANS:  D                    TOP:   The R-S and E-Z Conventions

 

  1. Which of the following structures is (E)-2,3-dichloro-2-pentene?
 
 

 

A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  E                    TOP:   The R-S and E-Z Conventions

 

  1. Of the following structures, how many are classified E?
 
 

 

A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  C                    TOP:   The R-S and E-Z Conventions

 

  1. Of the following structures, how many are classified Z?
 
 

 

A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  C                    TOP:   The R-S and E-Z Conventions

 

  1. Which of the following structures depicts (R)-3-ethyl-2,3-dimethylhexane?
A)   D)  
B)   E)  
C)    

 

 

ANS:  B                    TOP:   The R-S and E-Z Conventions

 

  1. The priority order for R/S nomenclature is
A) CH=CH2 > OH > CH3 > CH2CH3
B) OH > CH2CH3 > CH=CH2 > CH3
C) OH > CH=CH2 > CH2CH3 > CH3
D) CH3 > CH2CH3 > CH=CH2 > OH
E) CH2CH3 > CH3 > CH=CH2 > OH

 

 

ANS:  C                    TOP:   The R-S and E-Z Conventions

 

  1. Which name describes the following structure?

 

A) (R)-3-methyl-1-penten-3-ol
B) (S)-3-methyl-1-penten-3-ol
C) (R)-3-ethyl-1-buten-3-ol
D) (R)-3-methyl-1-pentyn-3-ol
E) (S)-3-ethyl-1-buten-3-ol

 

 

ANS:  A                    TOP:   The R-S and E-Z Conventions

 

  1. Which name describes the following structure?

 

A) (R)-4-methyl-1-hexen-4-ol
B) (S)-4-ethyl-1-penten-4-ol
C) (R)-4-ethyl-1-penten-3-ol
D) (S)-4-methyl-1-hexen-4-ol
E) (S)-4-methyl-1-hexyn-4-ol

 

 

ANS:  D                    TOP:   The R-S and E-Z Conventions

 

  1. What is correct name for the following structure?
 

 

A) (R,S)-2,3-dichlorobutane
B) (2R,3S)-2,3-dichlorobutane
C) (2S,3S)-2,3-dichlorobutane
D) (2R,3R)-2,3-dichlorobutane
E) none of these

 

 

ANS:  D                    TOP:   Fischer and Newman Projections

 

  1. What is the absolute configuration around C-2 and C-3?
 

 

 

A) R, R
B) S, S
C) R, S
D) S, R
E) E, Z

 

 

ANS:  A                    TOP:   Fischer and Newman Projections

 

  1. The absolute configuration around the stereogenic center of the molecule below is:
 

 

A) R
B) S
C) E
D) Z
E) trans

 

 

ANS:  A                    TOP:   Fischer and Newman Projections

 

  1. The Fischer projection formula for (S)-lactic acid (2-hydroxypropanoic acid) is
A)   D)  
B)   E)  
C)    

 

 

ANS:  E                    TOP:   Fischer and Newman Projections

 

  1. The Fischer projection that represents the same molecule as  is:

 

A)   D)  
B)   E)  
C)    

 

 

ANS:  C                    TOP:   Fischer and Newman Projections

 

  1. represents

 

A) (2R,3R)-2,3-butanediol.
B) (2S,3S)-2,3-butanediol.
C) the most stable conformer of (2R,3R)-2,3-butanediol.
D) the least stable conformer of (2R,3R)-2,3-butanediol.
E) meso-2,3-butanediol.

 

 

ANS:  E                    TOP:   Fischer and Newman Projections

 

  1. Which one of the following structures represents a meso compound?
A)   D)  
B)   E)  
C)    

 

 

ANS:  A                    TOP:   Fischer and Newman Projections

 

  1. When (R)-3-bromo-2-methyl-1-butene is reacted with HBr, two stereoisomers are formed.  What is the relationship of these stereoisomers?
A) enantiomers
B) meso compounds
C) diastereomers
D) E
E) Z

 

 

ANS:  C                    TOP:   Stereochemistry and Chemical Reactions

 

  1. Treating 1-butene with HBr produces a product with one stereogenic carbon.  What is the name of the product?
A) 2-bromo-1-butene
B) 1-bromobutane
C) (R)-2-bromobutane
D) (S)-2-bromobutane
E) both C and D in equal amounts

 

 

ANS:  E                    TOP:   Stereochemistry and Chemical Reactions

 

  1. When (S)-3-bromo-1-butene is treated with HBr, two stereoisomeric products form.  What is the relationship of these two products?
A) enantiomers
B) diastereomers
C) meso compounds
D) racemic mixture
E) cis/trans

 

 

ANS:  B                    TOP:   Stereochemistry and Chemical Reactions

 

  1. How many stereogenic carbons are produced from the following sequence of reactions?

 

 

A) 1
B) 2
C) 3
D) 4
E) 5

 

 

ANS:  B                    TOP:   Stereochemistry and Chemical Reactions

 

  1. Enantiomers may differ in the following property:
A) the rate at which they react with a chiral reagent
B) boiling point
C) melting point
D) number of degrees they rotate plane polarized light
E) solubility in water

 

 

ANS:  A                    TOP:   Stereochemistry and Chemical Reactions

 

  1. The product of addition of bromine to (R)-3-buten-2-ol will be
A) a 50:50 mixture of enantiomers.
B) a mixture of enantiomers formed in unequal amounts.
C) a 50:50 mixture of diastereomers.
D) a mixture of diastereomers formed in unequal amounts.
E) optically inactive.

 

 

ANS:  D                    TOP:   Stereochemistry and Chemical Reactions

 

Chapter 17 Amino Acids, Peptides, and Proteins

 

MULTIPLE CHOICE

 

  1. Which of the following molecules is a-aminopropanoic acid?
A)   D)  
B)   E)  
C)    

 

 

ANS:  B                    TOP:   Nomenclature

 

  1. What is the name of the following molecule?
 

 

 

 

 

 

A) 3-amino-3-phenylvaleric acid
B) 4-amino-4-methyl-4-phenylbutanoic acid
C) 4-amino-4-phenylpentanoic acid
D) 4-amino-4-phenyl-4-methylbutanoic acid
E) 2-amino-2-phenylbutanoic acid

 

 

ANS:  C                    TOP:   Nomenclature

 

  1. What is the only a-amino acid that does not have a stereogenic carbon?
A) glycine
B) alanine
C) phenylalanine
D) valine
E) leucine

 

 

ANS:  A                    TOP:   Nomenclature

 

  1. Which one of the following represents a tetrapeptide?
A) Val-Ile-Asp-Asp
B) Ala-Ala-Ala-Ala-Val-Val
C) Ala-Ser-Val-Val-Ile
D) Ser-Ser-Ala-Ala-Gly-Gly-Glu-Glu
E) Ser-Ala-Thr-Pro-Leu

 

 

ANS:  A                    TOP:   Nomenclature

 

  1. In the octapeptide, Cys-Ile-Ser-Asp-Gly-His-Gly-Gly, which is the N-terminal amino acid?
A) Ser
B) Ile
C) Asp
D) Cys
E) Gly

 

 

ANS:  D                    TOP:   Nomenclature

 

  1. What is the name of the amide bond linking two amino acids?
A) ionic
B) hydrogen
C) glycosidic
D) nonpolar
E) peptide

 

 

ANS:  E                    TOP:   Nomenclature

 

  1. In the octapeptide, Phe-Ile-Ser-Asp-Gly-His-Gly-Tyr, which is the C-terminal amino acid?
A) Ser
B) Phe
C) Tyr
D) His
E) Gly

 

 

ANS:  C                    TOP:   Nomenclature

 

  1. Which of the following a-amino acids contains an imidazole?
A) arginine
B) asparagine
C) aspartic acid
D) histidine
E) tyrosine

 

 

ANS:  D                    TOP:   Nomenclature

 

  1. Which molecule is an a-amino acid?
A)   D)  
B)   E)  
C)    

 

 

ANS:  C                    TOP:   Structure

 

  1. To what family of polymers do proteins belong?
A) polyesters
B) polyacids
C) polyamines
D) polyurethanes
E) polyamides

 

 

ANS:  E                    TOP:   Structure

 

  1. Which of the following a-amino acids contains a hydroxyl group?
A) asparagine
B) threonine
C) cysteine
D) isoleucine
E) phenylalanine

 

 

ANS:  B                    TOP:   Structure

 

  1. How many different combinations are possible for a tripeptide containing one of each of the following amino acids: Phe, Val, Asp?
A) 2
B) 6
C) 8
D) 10
E) greater than 10

 

 

ANS:  B                    TOP:   Structure

 

  1. Which of the following amino acids can form disulfide bonds?
A) Gly
B) His
C) Cys
D) Asp
E) Glu

 

 

ANS:  C                    TOP:   Structure

 

  1. What is the correct relationship between valylalanine and alanylvaline?
A) enantiomeric pair
B) meso compounds
C) structural isomers
D) geometric isomers
E) racemic mixture

 

 

ANS:  C                    TOP:   Structure

 

  1. Hydrogen bonds, a-helices, and pleated sheets are               structural properties of proteins.
A) primary
B) secondary
C) tertiary
D) quaternary
E) sole

 

 

ANS:  B                    TOP:   Structure

 

  1. The dipeptides are

 

A) constitutional isomers.
B) stereoisomers.
C) diastereoisomers.
D) enantiomers.
E) identical.

 

 

ANS:  A                    TOP:   Structure

 

  1. In the dipeptide shown the following segment of the molecule is likely to lie in a single plane:
 

 

A)  
B)  
C)  
D)  
E)  

 

 

ANS:  D                    TOP:   Structure

 

  1. How many different combinations are possible for a tetrapeptide containing two glycines  (Gly,) one alanine (Ala,) and one phenylalanine (Phe)?
A) 3
B) 6
C) 12
D) 24
E) 36

 

 

ANS:  C                    TOP:   Structure

 

  1. Under what condition would phenylalanine exist as follows?
A) at a low pH
B) at a high pH
C) at the pI
D) when pH = pKa
E) none of these

 

 

ANS:  B                    TOP:   Acid-Base Chemistry

 

  1. What is the net charge of isoleucine at its isoelectric point?
A) 0
B) +1
C) +2
D) 1
E) 2

 

 

ANS:  A                    TOP:   Acid-Base Chemistry

 

  1. If an amino acid has one carboxyl group and one amino group, and the pKas are 2.4 and 9.8 respectively, what is its isoelectric point?
A) 3.7
B) 6.1
C) 7.0
D) 7.9
E) 12.2

 

 

ANS:  B                    TOP:   Acid-Base Chemistry

 

  1. Based on the pKas of aspartic acid shown below, what is its approximate isoelectric point?
 

 

 

                                     

 

A) 2
B) 3
C) 5
D) 7
E) 10

 

 

ANS:  B                    TOP:   Acid-Base Chemistry

 

  1. Which of the following will migrate toward the positive electrode in an electrophoresis experiment?
 

 

 

 

 

 

A) I
B) II
C) III
D) I and III
E) none will migrate

 

 

ANS:  B                    TOP:   Acid-Base Chemistry

 

  1. Based on the equilibria shown below, what is the net charge on structure IV?
 

 

A) 2
B) 1
C) 0
D) +1
E) +2

 

 

ANS:  A                    TOP:   Acid-Base Chemistry

 

  1. At the isoelectric point, the structure of methionine (2-amino-4-methylthiobutanoic acid) is:
A)   D)  
B)   E)  
C)    

 

 

ANS:  D                    TOP:   Acid-Base Chemistry

 

  1. The isoelectric pH (pI) of  is likely to be at a pH that is

 

A) below pK1.
B) at pK1.
C) between pK1 and pK2.
D) at pK2.
E) above pK2.

 

 

ANS:  C                    TOP:   Acid-Base Chemistry

 

  1. The structure of  at the isoelectric point is:

 

A)   D)  
B)   E)  
C)    

 

 

ANS:  B                    TOP:   Acid-Base Chemistry

 

  1. Which reagent is used to determine the N-terminal amino acid of a peptide?
A) Jones
B) Fehlings
C) Ninhydrin
D) Sangers
E) Tollens

 

 

ANS:  D                    TOP:   Structure Determination

 

  1. What fragments will be obtained by a trypsin hydrolysis of the following octapeptide?

Ala-Val-Trp-Lys-Phe-Gly-Arg-Met

A) Ala-Val-Trp-Lys-Phe and Gly-Arg-Met
B) Ala-Val-Trp-Lys-Phe -Gly and Arg-Met
C) Ala-Val-Trp-Lys and Phe-Gly-Arg and Met
D) Ala-Val-Trp-Lys and Phe and Gly-Arg and Met
E) Ala-Val-Trp and Lys-Phe-Gly and Arg-Met

 

 

ANS:  C                    TOP:   Structure Determination

 

  1. Which reagent is used specifically to cleave the C-terminal amino acid of a peptide?
A) trypsin
B) carboxypeptidase
C) cyanogen bromide
D) chymotrypsin
E) HCl/H2O

 

 

ANS:  B                    TOP:   Structure Determination

 

  1. Which of the following is Sangers reagent?
A)   D)  
B)   E)  
C)    

 

 

ANS:  B                    TOP:   Structure Determination

 

  1. Bradykinin is a nonapeptide, Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg. In addition to one mole of Arg, what peptides are present after hydrolysis of bradykinin with chymotrypsin?
A) Arg-Pro-Pro and Gly-Phe and Ser-Pro-Phe
B) Pro-Pro-Gly and Phe-Ser-Pro-Phe-Arg
C) Arg-Pro-Pro-Gly-Phe and Ser-Pro-Phe
D) Arg-Pro-Pro-Gly-Phe-Ser and Pro-Phe
E) Pro-Pro-Gly and Phe-Ser-Pro-Phe-Arg

 

 

ANS:  C                    TOP:   Structure Determination

 

  1. What is the structure of the phenylhydantoin derived from the first cycle of the Edman degradation of Phe-Ala-Ser?
A) D)
B) E)
C)  

 

 

ANS:  B                    TOP:   Structure Determination

 

  1. A useful reagent for detecting amino acids is
A) hydrogen peroxide.
B) Tollens reagent.
C) ninhydrin.
D) Benedicts reagent.
E) Merrifields reagent.

 

 

ANS:  C                    TOP:   Structure Determination

 

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