Chemistry for Biological Sciences Study
Guide Questions
Course Introduction
Chemistry for Biological Sciences provides an essential foundation in chemical principles with an emphasis on their applications in biological systems. This course covers topics such as atomic and molecular structure, chemical bonding, thermodynamics, kinetics, acids and bases, and introductory organic chemistry, all contextualized within biological processes. Through lectures, laboratory experiments, and problem-solving activities, students will gain an understanding of how chemical concepts underpin key biological phenomena such as metabolism, cellular respiration, and molecular interactions, preparing them for further study in the life sciences.
Recommended Textbook
Organic Chemistry 8th Edition by Paula Yurkanis Bruice
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Page 2
Chapter 1: Remembering General Chemistry: Electronic
Structure and Bonding
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Sample Questions
Q1) Identify the compound with the weakest bond.
A)H<sub>2</sub>
B)HF
C)HCl
D)HBr
E)HI
Answer: E
Q2) Triethylamine [(CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>N] is a molecule in which the nitrogen atom is ________ hybridized and the CNC bond angle is
A)sp<sup>2</sup>,>109.5°
B)sp<sup>2</sup>,<109.5°
C)sp<sup>3</sup>,>109.5°
D)sp<sup>3</sup>,<109.5°
E)sp,109.5°
Answer: D
Q3) BF<sub>3</sub> has a dipole moment of zero.Propose a structure for BF<sub>3</sub> that is consistent with this information.
Answer: BF<sub>3</sub> is trigonal planar. 11ea8a1c_2c6d_766e_b657_bfe266551fe1_TB1831_00
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
Q2) Would you predict trifluoromethanesulfonic acid,CF<sub>3</sub>SO<sub>3</sub>H,to be a stronger or weaker acid than methanesulfonic acid,CH<sub>3</sub>SO<sub>3</sub>H? Explain your reasoning.
Answer: Trifluoromethanesulfonic acid is a stronger acid.Compare the strengths of the conjugate bases and remember that the weaker the base,the stronger the conjugate acid.In the case of the trifluoro derivative,the presence of the highly electronegative fluorine atoms serves to delocalize the negative charge to a greater extent.This additional delocalization makes trifluoromethanesulfonate a weaker base.
Q3) H-A is an acid with a pKa of 4.5.Which of the following statements about an aqueous solution of H-A is true?
A)At pH = 4.5,the solution contains much more H-A than.A<sup>-</sup>.
B)At pH = 4.5,the solution contains much more A<sup>-</sup> than H-A.
C)At pH- 3.5,the solution contains about 90% A<sup>-</sup> and 10% H-A.
D)At pH = 6.5,the solution contains about 80% A<sup>- and 20% H-A</sup>.
E)At pH = 5.5,the solution contains about 90% A<sup>-</sup> and 10% H-A.
Answer: E
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Chapter 3: An Introduction to Organic Compounds:
Nomenclature, physical Properties, and Structure
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Sample Questions
Q1) Which of the compounds below will form hydrogen bonds between its molecules?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>F
B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
C)(CH<sub>3</sub>)<sub>3</sub>N
D)CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub>
E)CH<sub>3</sub>NHCH<sub>2</sub>CH<sub>3</sub>
Answer: E
Q2) Provide the chair structure of cis-decalin,two cis-fused six-membered rings.
Answer: 11ea8a1c_2c7f_9f52_b657_93cf9ae01146_TB1831_00
Q3) Use a sawhorse structure to depict the eclipsed conformer of ethane.
Answer: 11ea8a1c_2c7c_b90d_b657_5367c2365501_TB1831_00
Q4) Which of the following will have the lowest boiling point?
A)CH<sub>3</sub>Cl
B)CH<sub>4</sub>
C)CH<sub>2</sub>Cl<sub>2</sub>
D)CHCl<sub>3</sub>
E)CCl<sub>4</sub>
Answer: B
Page 5
Q5) Draw the most stable conformer of trans-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030d_b657_778a7cd7007c_TB1831_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) How many stereoisomers exist with the following basic connectivity?
CH<sub>3</sub>CHClCH<sub>2</sub>CHClCH<sub>3</sub>
E)4
Q2) The specific rotation of a pure substance is -5.90°.What is the percentage of this isomer in a mixture with an observed specific rotation of -2.95°?
A)25%
B)50%
C)75%
D)80%
E)0%
Q3) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.
Q4) A sample of (+)and (-)-3-chlorohexane has a rotation of -20 degrees.Pure (+)-3-chlorohexane has a rotation of +40 degrees.Calculate the enantiomeric excess and the amount of (-)and (+)-3-chlorohexane in the original sample.
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Page 6
Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) An increase in which of the following will occur if the reaction temperature is increased? I.Energy of activation
II)Collision frequency
III)Fraction of collisions with sufficient energy
A)I and II
B)I and III
C)II and III
D)I,II,and III
E)I
Q2) How many degrees of unsaturation are present in a molecule with formula C<sub>10</sub>H<sub>16</sub>?
A)1
B)2
C)3
D)4
E)5
Q3) Under what conditions is G° equal to H° for a chemical reaction?
Q4) Draw the structure of (Z)-1-chloro-2-methyl-2-butene.
Page 7
Q5) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
Q6) Why do reactions tend to proceed at a faster rate as T increases?
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Chapter 6: The Reactions of Alkenes - the Stereochemistry
of Addition Reactions
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Sample Questions
Q1) What is the product of the hydrogenation of an alkene?
A)dihaloalkane
B)alkane
C)haloalkane
D)alcohol
E)ether
Q2) A reaction in which a mixture of two constitutional isomers is obtained but one is formed in higher amounts than the other is called a
A)regioselective reaction.
B)regiospecific reaction.
C)stereospecific reaction.
D)stereoselective reaction.
E)successful reaction.
Q3) Which statement is true in the hydroboration-oxidation of an alkene?
A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markovnikov orientation and both syn and anti addition occur.
Q4) What is hyperconjugation,and how does it affect carbocation stability?
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
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Sample Questions
Q1) Write structures and give IUPAC names for all alkynes with molecular formula C<sub>5</sub>H<sub>8</sub>.
Q2) Provide the structure of the major organic product that results when 2-butyne is treated with HgSO<sub>4</sub>/H<sub>2</sub>SO<sub>4</sub> in water.
Q3) Provide the structure of the major organic product that results when 2-butyne is treated with H<sub>2</sub> in the presence of Lindlar's catalyst.
Q4) Provide the structure of all distinct terminal alkynes with a molecular formula of C<sub>6</sub>H<sub>10</sub>.
Q5) Provide the structure of (2E,4E)-2-chloro-2,4-octadiene.
Q6) Which of the alkyne addition reactions below involves an enol intermediate?
A)hydroboration/oxidation
B)treatment with HgSO<sub>4</sub> in dilute H<sub>2</sub>SO<sub>4</sub>
C)hydrogenation
D)both A and B
E)both A and C
Q7) Why are terminal alkynes more acidic than other hydrocarbons?
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Q8) Give the IUPAC name for BrCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>2</sub>CH<sub>3</sub>.
Electronic Effects: an Introduction to the Reactions of
Benzene
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Sample Questions
Q1) Provide the structure of indole.
Q2) Which of the following terms best describes a Diels-Alder reaction?
A)a [4+2] cycloaddition
B)a [2+2] cycloaddition
C)a sigmatropic rearrangement
D)a 1,3-dipolar cycloaddition
E)a substitution reaction
Q3) Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing H° of this reaction.The most negative H° should be listed first.
cis-2-pentene,2,3-pentadiene,and trans-1,3-pentadiene
Q4) What descriptive term is applied to the type of diene represented by 2,4-hexadiene?
A)conjugated diene
B)cumulated diene
C)isolated diene
D)alkynyl diene
E)none of the above
Page 11
Q5) Is cyclooctatetraene a planar molecule? Explain.
Q6) Give the hybridization,shape,and bond angle of a carbon in benzene.
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12
Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Sample Questions
Q1) Assuming no other changes,what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?
A)no change
B)doubles the rate
C)triples the rate
D)quadruples the rate
E)rate is halved
Q2) Which of the following is the rate law for S<sub>N</sub>1 mechanisms?
A)Rate = k[Alkyl Halide] [Nucleophile]
B)Rate = k[Nucleophile]
C)Rate = k[Alkyl Halide]
D)Rate = k[Alkyl Halide] [Nucleophile] + k<sub>2</sub>[Alkyl Halide]
E)Rate = k<sub>1</sub>[Alkyl Halide] + k<sub>2</sub>[Nucleophile]
Q3) What type of solvent is best for S<sub>N</sub>2 reactions which employ anionic nucleophiles: polar,protic solvents; polar,aprotic solvents; or nonpolar solvents? Explain.
Q4) Which base,ammonia (NH<sub>3</sub>)or triethylamine [(CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>N],would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly.
Page 13
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Chapter 10: Reactions of Alcohols, ethers, epoxides, amines and
Sulfur-Containing Compounds
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Sample Questions
Q1) Which of the following reagents is best used in the conversion of methyl alcohol to methyl chloride?
A)Cl<sub>2</sub>/CCl<sub>4</sub>
B)Cl<sub>2</sub>/h
C)Cl<sup>-</sup>
D)SOCl<sub>2</sub> E)NaCl
Q2) Which of the following alcohols will react most rapidly with the Lucas reagent (HCl,ZnCl<sub>2</sub>)?
A)(CH<sub>3</sub>)<sub>3</sub>COH
B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH C)CH<sub>3</sub>CHOHCH<sub>2</sub>CH<sub>3</sub> D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH
Q3) Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in the presence of HBr.
Q4) How are certain arene oxides believed to cause cancer?
Q5) Provide the structure of the major organic product which results when naphthalene oxide undergoes rearrangement in the presence of water.Explain the regioselectivity of this rearrangement.
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Chapter 11: Organometallic Compounds
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Sample Questions
Q1) Which of the following sequences of reactions would be best when converting cyclohexene oxide into propylcyclohexane? A)1)CH<sub>3</sub>CCNa 2.H<sub>3</sub>O<sup>+</sup> B)1)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr 2.H<sub>2</sub>SO<sub>4</sub>, 3.H<sub>2</sub>,Pt C)1)H<sub>3</sub>O<sup>+</sup> 2.CH<sub>3</sub>CCNa D)1)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li 2.HBr E)1)H<sub>3</sub>PO<sub>4</sub>, 2.CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr 3.H<sup>+</sup>
Q2) Complete and balance the following reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li + CuI
Q3) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q4) The following alkyl halide could not be used to form a Grignard reagent.Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q5) Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain briefly.
Q6) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + CdCl<sub>2</sub>
Page 15
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Chapter 12: Radicals
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Sample Questions
Q1) Show the propagating steps in the addition of HBr to 1-pentene in the presence of peroxide.
Q2) The reaction Br<sub>2</sub> + CH<sub>3</sub>Br CH<sub>2</sub>Br<sub>2</sub> + HBr was carried out.Which of the following mechanism steps is both productive and relatively likely to occur?
A)Br + CH<sub>2</sub>Br CH<sub>2</sub>Br<sub>2</sub>
B)Br + CH<sub>3</sub> CH<sub>3</sub>Br
C)Br + Br<sub>2</sub> Br<sub>2</sub> + Br
D)Br + CH<sub>3</sub>Br HBr + CH<sub>2</sub>Br
Q3) Rank the following fractions which result from the fractional distillation of petroleum in order of increasing boiling point: asphalt,gasoline,kerosene,natural gas,heating oil.
Q4) How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.
Q5) Write an equation to describe the initiation step in the chlorination of methane.
Q6) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.
Q7) Species with unpaired electrons are called ________.
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Sample Questions
Q1) Which compound has the lowest carbonyl absorption frequency in an infrared spectrum?
A)ester
B)ketone
C)amide
D)aldehyde
E)carboxylic acid
Q2) Which of the following statements best explains how a hydrocarbon can show an M+2 peak in mass spectrometry?
A)from <sup>13</sup>C and <sup>1</sup>H
B)from <sup>12</sup>C and <sup>2</sup>H
C)from a single <sup>13</sup>C
D)from a single <sup>3</sup>H
E)from two <sup>13</sup>C's
Q3) Which compound's carbonyl stretch occurs at the lowest wavenumber?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
B)CH<sub>3</sub>COCH<sub>2</sub>CH<sub>3</sub> C)CH<sub>3</sub>CH<sub>2</sub>CONH<sub>2</sub>
D)CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> E)CH<sub>3</sub>CH<sub>2</sub>COCH<sub>2</sub>CH<sub>3</sub>
Page 17
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Chapter 14: Nmr Spectroscopy
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Sample Questions
Q1) An unknown compound,C<sub>4</sub>H<sub>10</sub>O,gave the following proton NMR data:
Triplet at 1.13 ppm
Quartet at 3.38 ppm
What is the structure of the compound?
Q2) What multiplicities are observed in the spin coupled <sup>13</sup>C NMR spectrum of 2,3-dimethyl-2-butene?
Q3) Deduce the identity of the following compound from the <sup>1</sup>H NMR spectral data given.
C<sub>8</sub>H<sub>18</sub>O : 0.89 (6H,doublet),1.87 (1H,multiplet),3.17 (2H,doublet)(ppm)
Q4) How many signals would you expect to see in the <sup>1</sup>H NMR spectrum of the following compound? ClCH<sub>2</sub>CH<sub>2</sub>Cl
Q5) What is indicated by a cross peak in the COSY spectrum of a compound?
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Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid
Derivatives
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Q1) In which of the following compounds does the carbonyl stretch in the IR spectrum occur at the lowest wavenumber?
A)cyclohexanone
B)ethyl acetate
C)propanoyl chloride
D)pentanamide
E) -butyrolactone
Q2) What are the products of the reaction of benzoic acid with thionyl chloride?
Q3) Why are -lactams,such as penicillins and cephalosporins,unusually reactive amides?
Q4) Give a detailed,stepwise mechanism for the Fischer esterification of acetic acid with methanol.
Q5) Which of the following intermediates is present in the acid-catalyzed hydrolysis of t-butylacetate but not in the acid-catalyzed hydrolysis of methyl acetate?
A)a protonated carbonyl
B)a carbocation
C)a carbanion
D)a carboxylate anion
E)1-propanol
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Chapter 16: Reactions of Aldehydes and Ketones
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Sample Questions
Q1) Provide the major organic product of the reaction of aniline with 3-pentanone.
Q2) Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.
Q3) Draw the structure of 3-bromobutanal.
Q4) Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H<sub>2</sub>NOH.
Q5) What is the major product when (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>Br is subjected to the following reaction sequence: 1.Mg,ether 2.CO<sub>2</sub> 3.H<sub>3</sub>O<sup>+ </sup>?
A)3-methyl-1-butanol
B)2-methyl-2-butanol
C)4-methyl-1-pentanol
D)4-methylpentanoic acid
Q6) Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.
Q7) Draw the structure of 3,3-dimethyl-4-oxopentanal.
Q8) Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.
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Chapter 17: Reactions at the -Carbon
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Q1) When the 1,7-diester
CH<sub>3</sub>O<sub>2</sub>CCH<sub>2</sub>CH<sub>2</sub>CH(CH<sub>3</sub>) CH<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?
A)an acyclic -diketone
B)an acyclic -ketoacid
C)an acyclic -diester
D)a cyclic -ketoester
E)a cyclic -diketone
Q2) Which of the following compounds will give a positive iodoform test?
A)propanal
B)2-pentanone
C)3-pentanone
D)benzophenone
E)cyclohexanone
Q3) Show how an enolate can add to a carbonyl.
Q4) Provide a detailed,stepwise mechanism for the base-catalyzed enolization of acetaldehyde.
Q5) Provide a detailed,stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) Provide the structure of benzenesulfonic acid.
Q2) Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E<sup>+</sup>.
Q3) Provide the structure of benzoic acid.
Q4) What specific electrophile is attacked by benzene when it undergoes nitration?
A)HNO<sub>3</sub>
B)NO<sub>3</sub>
C)NO
D)NO<sub>2</sub>
E)NO<sub>2</sub><sup>+</sup>
Q5) Provide the structure of anisole.
Q6) Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene?
A)Benzene functions as a nucleophile.
B)Formation of a carbocation intermediate is the rate-determining step.
C)The carbocation intermediate contains an sp<sup>3</sup> hybridized carbon in the ring.
D)The addition product is a frequent minor product.
E)Aromaticity is regained by loss of H<sup>+</sup>.
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) Show how the dipole moments are oriented in pyrrolidine and pyrrole,and explain why they are oriented in opposite directions.
Q2) Which heterocyclic ring is present in heme?
A)pyrrole
B)purine
C)pyrimidine
D)pyridine
E)porphyrin
Q3) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Q4) When benzofuran is treated with acetic anhydride,the major organic product is
A)2-acetylbenzofuran.
B)3-acetylbenzofuran.
C)4-acetylbenzofuran.
D)5-acetylbenzofuran.
E)7-acetylbenzofuran.
Q5) Draw the structures of the keto forms of both 2-hydroxypyridine and 4-hydroxypyridine.
Q6) Draw 2-methylpyrrolidine.
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) When pure -D-glucopyranose is dissolved in water,the optical rotation of the resulting solution changes over a period of time.What is the name of this phenomenon and why does it occur?
Q2) An optically active D-aldopentose produced an optically inactive alditol upon treatment with NaBH<sub>4</sub>.When this aldopentose was subjected to a Ruff degradation,a D-aldotetrose was generated.This aldotetrose gave an optically active aldaric acid upon oxidation with HNO<sub>3</sub>.Use these data to provide the structure of the starting D-aldopentose.
Q3) Provide the Fischer projection of the open-chain form of the aldonic acid which results when L-glucose is treated with bromine water.
Q4) Sucrose is a disaccharide is the table sugar.It consists of A)glucose. B)fructose. C)lactose.
D)A and B E)all of the above.
Q5) Provide the structure of the product which results when D-ribose is treated with bromine water.
Q6) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?
Page 24
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Treatment of a decapeptide with Edman's reagent releases PTH-Ala.What conclusion can be drawn regarding the decapeptide's primary structure?
Q2) Give a detailed,stepwise mechanism for the formation of the activated acyl derivative from the reaction of an amino acid with N,N'-dicyclohexylcarbodiimide.
Q3) Draw glutamate.
Q4) What is an amino acid analyzer?
Q5) Three dimensional structure of the peptides is also called a
A)primary structure.
B)secondary structure.
C)tertiary structure.
D)ternary structure.
E)quaternary structure.
Q6) The quaternary structure of proteins is concerned with which of the following?
A)sequence of amino acids in the peptide chain
B)description of the way the peptide chains are arranged with respect to each other C)location of the disulfide bridges in the peptide chain
D)conformation of the protein backbone
E)three-dimensional arrangement of all atoms in the protein
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Sample Questions
Q1) Which amino acid component is most likely to serve as a proton donor in an enzyme's active site?
A)methionine
B)glutamic acid
C)valine
D)phenylalanine
E)pyroline
Q2) Explain what is meant by site-specific mutagenesis.
Q3) Which of the following residues acts as a general-acid catalyst in aldolase but as a general-base catalyst in chymotrypsin?
A)methionine
B)histidine
C)cysteine
D)asparagine
E)lysine
Q4) Explain what is meant by anchimeric assistance and give an example.
Q5) How does an acid catalyst increase the rate of reaction?
26
Q6) How does a metal catalyst increase the rate of reaction?
Q7) How does Zn<sup>2+</sup> catalyze the hydrolysis of trifluoroacetate esters?
Q8) Explain the phenomenon known as molecular recognition.Give an example.
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Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
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Sample Questions
Q1) A quinone is part of the structure of vitamin A)B<sub>12</sub>.
B)B<sub>1</sub>.
C)B<sub>2</sub>.
D)C)
E)K)
Q2) The common name of vitamin B<sub>1</sub> is A)niacin.
B)riboflavin. C)thiamine.
D)biotin. E)panthothenate.
Q3) Which of the following are required species for biotin-dependent enzymes?
A)ATP
B)Mg<sup>+2</sup>
C)HCO<sub>3</sub><sup>-</sup>
D)A and B
E)A,B,and C
Q4) Which type of vitamins,water-soluble or lipid-soluble,can cause overdose?
Page 28
Q5) List the four stages of catabolism and briefly explain the significance of each.
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Chapter 24: The Organic Chemistry of the Metabolic Pathways
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Sample Questions
Q1) What three factors contribute to the greater stability of ADP and phosphate compared to ATP?
Q2) Complete the following concerning ATP's role as the universal carrier of chemical energy: "The energy ________ from the hydrolysis of ATP converts ________ reactions into ________ reactions."
A)released,exergonic,endergonic
B)released,endergonic,exergonic
C)consumed,exergonic,endergonic D)consumed,endergonic,exergonic
E)consumed,oxidation,reduction
Q3) Draw the structure of pyruvate.
Q4) What class of enzyme puts a phosphoryl group on its substrate?
Q5) To what reaction are many endergonic metabolic processes coupled in order to make them exergonic?
Q6) Describe what's happening mechanistically when glucose reacts with ATP to yield glucose-6-phosphate.
Q7) What compounds are formed when a carboxylate is phosphorylated by the attack at the b-phosphorus of ATP?
Q8) What explains the kinetic stability of ATP in aqueous media at biological pH? Page 29
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Chapter 25: The Organic Chemistry of Lipids
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Sample Questions
Q1) Squalene is a A)monoterpene.
B)sesquiterpene.
C)diterpene.
D)triterpene.
E)carotenoid.
Q2) Identify the compound with the highest melting point.
A)palmitic acid
B)lauric acid
C)stearic acid
D)myristic acid
E)linoleic acid
Q3) Most hormones are A)phosphoglycerides.
B)terpenes.
C)squalenes.
D)prostaglandins.
E)steroids.
Q4) Myristic acid has the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>12</sub>CO<sub>2</sub>H.Provide the structure of the triglyceride trimyristin.
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Chapter 26: The Chemistry of the Nucleic Acids
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Q1) For what compound is ATP an abbreviation?
A)adenine triphosphate
B)adenosine tetraphosphate
C)adenine tetraphosphate
D)adenosine triphosphate
E)adenine triphosphoric acid
Q2) Draw the structure of AMP.
Q3) Which of the following statements is not true about the structure of DNA as proposed by Watson and Crick?
A)The number of adenines in DNA is equal to the number of thymines.
B)The number of cytosines is equal to the number of guanines.
C)DNA consists of two strands of nucleic acids with the sugar-phosphate backbone on the inside and the bases on the outside.
D)The chains in DNA are held together by hydrogen bonding.
E)Adenine always pairs with thymine and guanine always pairs with cytosine.
Q4) Draw the structure of guanosine.
Q5) Draw the structure of TTP.
Q6) Show the hydrogen bonding which occurs when adenine and thymine form a base pair.
Q7) Draw the structure of cytidine 5'-phosphate.
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Chapter 27: Synthetic Polymers
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Q1) Why is chain branching less common in anionic polymerization than in cationic polymerization?
Q2) Identify the monomer(s)that undergo cationic polymerization.You may choose more than one answer.
A)styrene
B)methyl methacrylate
C)vinyl chloride
D)methyl vinyl ether
E)acrylamide
Q3) Identify the initiator in a radical polymerization.
A)KOH
B)BuLi
C)CH<sub>3</sub>OOCH<sub>3</sub>
D)BF<sub>3</sub>,H<sub>2</sub>O
E)HCl
Q4) What structural characteristic is shared by compounds used as radical initiators?
Q5) Provide the structure of the monomer from which Orlon [poly(acrylonitrile)] is prepared.
Q6) Describe what plasticizers are and give an example.
Page 33
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Chapter 28: Pericyclic Reactions
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Q1) Give the conditions for 1,7-hydrogen shifts.You may choose more than one answer.
A)suprafacial rearrangement
B)antarafacial rearrangement
C)thermal conditions
D)photochemical conditions
E)all of the above
Q2) Give a representation of the antibonding molecular orbital of the allyl anion.
Q3) Under what conditions would a 1,5-hydrogen shift occur in a sigmatropic rearrangement?
A)thermal conditions
B)photochemical conditions
C)suprafacial pathway
D)A and C
E)B and C
Q4) What are the three most common pericyclic reactions? Give examples.
Q5) What is meant by frontier orbitals?
Q6) Electrocyclic reactions are reversible.The cyclic compound is favored for electrocyclic reactions that form six-membered rings,whereas the open-chain compound is favored for reactions that form four-membered rings.Explain thoroughly in terms of the enthalpy changes that are occurring.
Page 34
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