Pre-Medical Chemistry Review
Questions
Course Introduction
Pre-Medical Chemistry is an introductory course designed to provide students with a foundational understanding of chemical principles essential for medical studies. Covering topics such as atomic and molecular structure, chemical bonding, stoichiometry, thermodynamics, kinetics, acids and bases, and organic functional groups, the course emphasizes their relevance to biological systems and human physiology. Through a combination of lectures, laboratory experiments, and problem-solving exercises, students will develop critical analytical skills and a scientific framework that supports advanced coursework in biology, biochemistry, and health sciences, preparing them for medical school or related health professions.
Recommended Textbook
Organic Chemistry 7th Edition by Paula Yurkanis Bruice
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Chapter 1: Remembering General Chemistry: Electronic
Structure and Bonding
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Sample Questions
Q1) Which of the following contain(s)polar covalent bonds?
A)NH<sub>3</sub>
B)Na<sub>2</sub>O
C)H<sub>2</sub>
D)KF
E)both A and C
Answer: A
Q2) How many nonbonding electron pairs, bonding electron pairs, pi bonds, and sigma bonds are present in CO<sub>2</sub>?
Answer: 4 nonbonding electron pairs, 4 bonding electrons pairs, 2 pi bonds, 2 sigma bonds
Q3) Give the hybridization, shape, and bond angle for the carbon in CO<sub>2</sub>.
Answer: sp, linear, 180
Q4) Identify the least electronegative atom.
Answer: B
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) 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.
Q2) Which of the following anions, CH<sub>3</sub>CHBrCO<sub>2</sub><sup></sup>or CH<sub>3</sub>CHFCO<sub>2</sub><sup>-</sup> is the stronger base?
Explain your choice.
Answer: CH<sub>3</sub>CHBrCO<sub>2</sub><sup>-</sup> is the stronger base. The more electronegative F atom can more effectively delocalize the negative charge via induction. This greater delocalization stabilizes CH<sub>3</sub>CHFCO<sub>2</sub><sup>- </sup>relative to CH<sub>3</sub>CHBrCO<sub>2</sub><sup>-</sup> and makes it a weaker base.
Q3) Give the conjugate acid and the conjugate base for HSO<sub>4</sub><sup>-</sup>.
Answer: conjugate acid: H<sub>2</sub>SO<sub>4</sub> conjugate base: SO<sub>4</sub><sup>2-</sup>
Page 4
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Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) Which of the molecules below has the higher boiling point? Briefly explain your choice.
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH or CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub>
Answer: CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH has the higher boiling point since it is capable of intermolecular hydrogen bonding.
Q2) There is something wrong with the following name. Write the structure and correct the name: 2-ethylpropane.
Answer: 11ea7d6e_0662_2035_8568_07790dde7422_TB1830_00_TB1830_00 The correct name is 2-methylbutane.
Q3) Provide the chair structure of cis-decalin, two cis-fused six-membered rings.
Answer: 11ea7d6e_0669_9a97_8568_4b548fc8e6b9_TB1830_00_TB1830_00
Q4) How many constitutional isomers are possible for C<sub>6</sub>H<sub>14</sub>?
Answer: B
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) Provide a careful structure for (2S,3R)-2,3-dibromohexane.
Q2) Provide a careful structure for (2R,3S,4S)-2-bromo-4-methyl-3-hexanol.
Q3) Which of the following statements correctly pertains to a pair of enantiomers?
A)They rotate the plane of polarized light by exactly the same amount and in opposite directions.
B)They rotate the plane of polarized light by differing amounts and in opposite directions.
C)They rotate the plane of polarized light by differing amounts and in the same direction.
D)They have different melting points.
E)They have the same melting point, but they have different boiling points.
Q4) Provide a perspective drawing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.
Q5) Draw the structure of (2R,3S)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.
Q6) A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?
Q7) Briefly describe how two enantiomers might be separated.
Page 6
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Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Which of the following is capable of exhibiting cis-trans isomerism?
A)1-butene
B)1-pentene
C)cyclohexene
D)ethene
E)2-butene
Q2) Which of the following is an allylic alcohol?
A)CH<sub>2</sub>=CHCH<sub>2</sub>OCH<sub>3</sub>
B)CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>3</sub>
C)HOCH=CHCH<sub>2</sub>CH<sub>3</sub>
D)CH<sub>3</sub>CH=CHCH<sub>2</sub>OH
E)CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>2</sub>OH
Q3) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
Q4) Draw the curved arrows to show how CH<sub>3</sub>CH=CHCH<sub>3</sub> reacts with HBr to form a carbocation.
Q5) Consider the conversion of C to D via a one-step mechanism. The activation energy of this conversion is 3 kcal/mol. The energy difference between D and the transition state of the reaction is 7 kcal/mol. Estimate H° for the reaction C D.
Q6) Draw the structure of (Z)-4-ethyl-3-methylheptene.
Page 7
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Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
Q2) Based on the relative stabilities of the intermediates involved, explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.
Q3) Give the intermediate for the halohydrin reaction.
A)a halonium ion
B)the most stable carbocation with OH on the adjacent carbon
C)the most stable carbocation with X on the adjacent carbon
D)a cyclic oxonium ion
E)the most stable carbanion
Q4) What is hyperconjugation, and how does it affect carbocation stability?
Q5) Which of the following compounds will react most rapidly with HCl?
A)5-methyl-1-hexene
B)4-methyl-1-hexene
C)(E)-5-methyl-2-hexene
D)(E)-2-methyl-3-hexene
E)2-methyl-2-hexene
Q6) Give the types of products formed from the bromination and catalytic hydrogenation (using D<sub>2</sub>)of cyclohexene.
Page 8
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Chapter 7: Reactions of Alkynes Introduction to Multistep Synthesis
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Sample Questions
Q1) Provide the structure of the major organic produt that results when 2-butyne is treated with HgSO<sub>4</sub>/H<sub>2</sub>SO<sub>4</sub> in water
Q2) A mixture of 1-heptyne, 2-heptyne, and 3-heptyne was hydrogenated in the presence of a platinum catalyst until hydrogen uptake ceased. If one assumes that the hydrogenation went to completion, how many distinct seven-carbon hydrocarbons were produced?
A)1
B)2
C)3
D)6
E)8
Q3) Describe a sequence of reactions by which the aldehyde CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CHO could be prepared from acetylene.
Q4) Describe a sequence of reactions by which butylbenzene can be prepared from phenylacetylene.
Q5) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q6) Why are terminal alkynes more acidic than other hydrocarbons?
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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory
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Sample Questions
Q1) Which of the following statements concerning resonance contributors and resonance hybrids is not correct?
A)The fewer nearly equivalent resonance contributors are in the structure, the greater the resonance energy.
B)A resonance hybrid is more stable than the predicted stability of any of its resonance contributors.
C)The greater the number of relatively stable resonance contributors, the greater the resonance energy.
D)The greater the predicted stability of a resonance contributor, the more it contributes to the resonance hybrid.
E)none of the above
Q2) In the acetate ion (CH<sub>3</sub>CO<sub>2</sub><sup>-</sup>), which of the oxygen atoms bears a greater negative charge? Explain your answer.
Q3) Provide the structure of the biologically significant heterocycle purine.
Q4) Provide the structure of indole.
Q5) What is the major product obtained from the addition of one mole of HCl at high temperature to 1,3-butadiene?
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Give the name(s)of the product(s)of the S<sub>N</sub>2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.
A)2,2-dimethyl-1-butanol
B)3,3-dimethyl-2-butanol
C)3,3-dimethyl-1-butanol
D)2,3-dimethyl-2-butanol
E)2,3-dimethyl-1-butanol
Q2) Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?
Q3) Identify the alkyl halide that reacts the fastest in a S<sub>N</sub>2 reaction.
A)2-chloro-2-methylpropane
B)2-chlorobutane
C)1-chlorobutane
D)chloromethane
Q4) Identify the alkyl halide that reacts the fastest in an S<sub>N</sub>2 reaction.
A)1-chloropropane
B)1-bromopropane
C)1-fluoropropane
D)1-iodopropane
Q5) Provide the structure of the major organic product in the following reaction. (CH<sub>3</sub>)<sub>3</sub>N + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>I
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Sample Questions
Q1) 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.
Q2) Which of the following correctly reflects relative stabilities of carbocations?
A)3° allylic > 2° > 1° benzylic
B)methyl > 2° benzylic > 3°
C)3° benzylic > vinyl > 1°
D)2° allylic > 2° > vinyl
E)1° benzylic > 3° > 3° allylic
Q3) Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?
A)S<sub>N</sub>1
B)S<sub>N</sub>2
C)E1
D)E2
E)none of the above
Q4) What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is heated in ethanol?
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Q5) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and
Sulfur-Containing Compounds
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Sample Questions
Q1) Draw the tosylate ion and explain why it is a particularly good leaving group.
Q2) When dipentyl ether is treated with excess HI, through what type of mechanism(s)does the major product result?
A)S<sub>N</sub>2
B)S<sub>N</sub>1
C)both S<sub>N</sub>1 and S<sub>N</sub>2
D)E1
E)E2
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) Which of the following is least likely to be found in the product mixture which results when 2,2-dimethyl-3-pentanol is heated in phosphoric acid?
A)(E)-4, 4-dimethyl-2-pentene
B)(Z)-4, 4-dimethyl-2-pentene
C)2, 3-dimethyl-2-pentene
D)2, 3-dimethyl-1-pentene
E)4, 4-dimethyl-1-pentene
Q5) How are certain arene oxides believed to cause cancer?
Q6) Why are alcohols typically poor electrophiles?
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Chapter 12: Organometallic Compounds
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Sample Questions
Q1) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q2) How would one use a Grignard-based synthesis to accomplish the following transformation?
benzyl bromide (PhCH<sub>2</sub>Br)to 3-phenyl-1-propanol
Q3) What two-word name is given to a reaction that breaks the carbon-carbon double bond and then rejoins the fragments with the double bonds forming in a different location?
Q4) 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>
Q5) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) Calculate the overall H° for the reaction shown given the bond dissociation energies (in kcal/mol)below: (CH<sub>3</sub>)<sub>3</sub>C-H + Cl-Cl (CH<sub>3</sub>)<sub>3</sub>C<sub> </sub>- Cl + H-Cl
91 58 78.5 103
A)+181.5 kcal/mole
B)+58.0 kcal/mole
C)+32.5 kcal/mole
D)-32.5 kcal/mole
E)-57.5 kcal/mole
Q2) Write an equation to describe the initiation step in the chlorination of methane.
Q3) Provide a series of synthetic steps by which (CH<sub>3</sub>)<sub>2</sub>C=CH<sub>2</sub> could be prepared from 2-methylpropane.
Q4) How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.
Q5) A hydrocarbon with molecular formula C<sub>5</sub>H<sub>12</sub> is subjected to free radical chlorination conditions and only one monochlorinated product resulted. Provide the structure of this product.
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) Which molecule below has two significant bands (medium and broad)in the 33003500 cm<sup>-1</sup> range of its IR spectrum?
A)(CH<sub>3</sub>)<sub>3</sub>N
B)CH<sub>3</sub>CH<sub>2</sub>NH2
C)CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>
D)CH<sub>3</sub>CON(CH<sub>3</sub>)<sub>2</sub>
E)CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>
Q2) Which region of the electromagnetic spectrum, IR or X-ray, is characterized by waves of lower frequency?
Q3) Which of the following is highest in energy per photon?
A)electromagnetic radiation with a wavenumber of 10<sup>-2</sup> cm<sup>-1</sup>
B)electromagnetic radiation with a frequency of 10<sup>7</sup> s<sup>-1</sup>
C)electromagnetic radiation with a frequency of 10<sup>5</sup> s<sup>-1</sup>
D)electromagnetic radiation with a wavelength of 10 cm
E)electromagnetic radiation with a wavenumber of 10<sup>6</sup> cm<sup>-1</sup>
Q4) Is it possible to have an M + 2 peak in mass spectrometry? Explain.
Q5) How could you distinguish the mass spectrum of 2,2-dimethylpropane from that of isopentane?
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Q6) How can UV spectroscopy be used to estimate the nucleotide composition of DNA?
Chapter 15: Nmr Spectroscopy
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Sample Questions
Q1) If two signals differ by 3 ppm, how do they differ in Hertz in a 60 MHz spectrometer?
A)20 Hz
B)300 Hz
C)360 Hz
D)180 Hz
E)90 Hz
Q2) Why is Fourier transform NMR spectroscopy preferred over continuous wave as a technique for <sup>13</sup>C NMR?
Q3) Predict the number of signals expected, their splitting, and their relative area in the <sup>1</sup>H NMR spectrum of CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub>.
Q4) Deduce the identity of the following compound from the spectral data given. C<sub>7</sub>H<sub>10</sub>O<sub>2</sub>: <sup>1</sup>H NMR, 1.16 (3H, singlet), 2.21 (2H, singlet); <sup>13</sup>C NMR, 216.25 (singlet), 52.57 (singlet), 34.51 (triplet), 20.22 (quartet)
Q5) Why is carbon-hydrogen coupling not generally seen in <sup>1</sup>H NMR spectra?
Q6) What is indicated by a cross peak in the COSY spectrum of a compound?
Q7) What information does a COSY spectrum give?
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Q8) Give one reason why <sup>13</sup>C NMR is less sensitive than <sup>1</sup>H NMR.
Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid
Derivatives
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Sample Questions
Q1) 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
Q2) Give a detailed, stepwise mechanism for the Fischer esterification of acetic acid with methanol.
Q3) Typically, amides will hydrolyze under ________ conditions than esters.
A)milder
B)more dilute
C)more vigorous
D)less vigorous
E)more saline
Q4) Palmitic acid (hexadecanoic acid)has a melting point of 63°C. Palmitoleic acid (9-hexadecenoic acid)has a melting point of 32°C. Explain this difference in melting points.
Q5) What reagents are used to dehydrate amides to nitriles?
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Chapter 17: Reactions of Aldehydes and Ketones
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Sample Questions
Q1) Propose a synthesis of 4-phenyl-2-butanol from 3-phenylpropanal.
Q2) An unknown compound (A), C<sub>10</sub>H<sub>12</sub>O, gave the following proton NMR data:
(a)triplet, at 1.0 ppm (3H)
(b)quartet, at 2.4 ppm (2H) (c)singlet, at 3.7 ppm (2H)
(d)multiplet, at 7.2 ppm (5H) Propose a structure for (A).
Q3) What class of organic compounds results when cyclopentanone reacts with ethylamine in the presence of trace acid?
A)cyanohydrin
B)semicarbazone
C)imine
D)enamine
E)oxime
Q4) Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.
Q5) Provide the structure of the compound that results when 4-heptanone is treated with peroxyacetic acid.
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Q1) Which of the following routes works best for the preparation of 3-ethylcyclohexanone from cyclohexanone?
A)1) LDA 2. Br<sub>2</sub> 3. CH<sub>3</sub>CH<sub>2</sub>MgBr B)1) Br<sub>2</sub>, H<sub>3</sub>O<sup>+</sup> 2. KOC(CH<sub>3</sub>)<sub>3</sub> 3. (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>CuLi 4. H<sub>3</sub>O<sup>+</sup> C)1) Br<sub>2</sub>, H<sub>3</sub>O<sup>+</sup> 2. CH<sub>3</sub>CH<sub>2</sub>OH,
D)1) NBS 2. Mg, ether 3. CH<sub>3</sub>CHO E)1) Br<sub>2</sub>, h 2. NaOH 3. NaOCH<sub>2</sub>CH<sub>3</sub> 4. H<sub>3</sub>O<sup>+</sup>
Q2) When compound X is heated, PhCOCH(CH<sub>3</sub>)<sub>2</sub> and CO<sub>2</sub> are produced. Offer a structure for compound X.
Q3) Rank the following compounds in order of increasing acidity of their a-Hs, least acidic to most acidic: CH<sub>3</sub>CH<sub>2</sub>CON(CH<sub>3</sub>)<sub>2</sub>, PhCOCH<sub>2</sub>CHO, CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, and PhCOCH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
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Q4) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Sample Questions
Q1) Identify the reaction(s)below that give benzoic acid as a product.
A)1-phenylethanol + manganese dioxide + heat
B)1-phenylethanol + sodium dichromate + acid + heat
C)tert-butylbenzene + sodium dichromate + acid + heat
D)ethylbenzene + sodium dichromate + acid + heat
E)phenylmethanol + manganese dioxide + heat
Q2) Bromination of benzene requires a Lewis acid catalyst while bromination of cyclohexene does not. Explain this difference in reactivity.
Q3) Which of the following aromatic rings is alkylated most rapidly by CH<sub>3</sub>CH<sub>2</sub>Cl/AlCl<sub>3</sub>?
A)benzene
B)ethylbenzene
C)chlorobenzene
D)benzenesulfonic acid
E)nitrobenzene
Q4) Provide the structure of anisole.
Q5) Provide the structure of benzoic acid.
Q6) What is the principle of microscopic reversibility?
Q7) Draw benzyl bromide.
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Chapter 20: More About Amines Heterocylic Compounds
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Q1) Draw the structures of the keto forms of both 2-hydroxypyridine and 4-hydroxypyridine.
Q2) Which of the following statements best describes the meaning of the term alkaloid?
A)heterocyclic natural products with a nitrogen as a heteroatom
B)natural, cyclic hydrocarbons
C)heterocyclic natural products with a sulfur as a heteroatom
D)heterocyclic natural products with an oxygen as a heteroatom
E)natural, cyclic hydrocarbons with alkyl groups
Q3) Which of the following lists the correct order of reactivity of the substrates in electrophilic aromatic substitution reactions?
A)thiophene > pyrrole > furan > benzene
B)benzene > furan > thiophene > pyrrole
C)furan > pyrrole > benzene > thiophene
D)benzene > pyrrole > thiophene > furan
E)pyrrole > furan > thiophene > benzene
Q4) Show how the dipole moments are oriented in pyrrolidine and pyrrole, and explain why they are oriented in opposite directions.
Q5) Draw 2-methylpyrrolidine.
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Chapter 21: Carbohydrates
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Q1) When -D-xylofuranose is treated with excess methyl iodide in the presence of Ag<sub>2</sub>O, how many equivalents of methyl iodide react with each equivalent of the furanose?
A)0
B)1
C)4
D)5
E)6
Q2) Which of the following would give a positive Tollen's test?
A) -D-glucopyranose
B)methyl -D-glucopyranoside
C)sucrose
D)methyl -D-ribofuranoside
E)none of the above
Q3) Draw the Fischer projection for the open-chain form of D-glucose.
Q4) Draw the more stable chair conformer of -D-glucopyranose.
Q5) Provide the Fischer projection of the open-chain form of the aldonic acid which results when L-glucose is treated with bromine water.
Q6) Draw L-erythrose.
Q7) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) When a disulfide linkage is formed, the compound containing this new linkage has been ________.
A)hydrolyzed
B)dehydrated
C)electrolyzed
D)oxidized
E)reduced
Q2) Which of the following amino acids has an aromatic R group?
A)serine
B)cysteine
C)asparagine
D)tyrosine
E)leucine
Q3) Which of the following best describes the side chain of arginine at a pH of 11?
A)hydrophobic
B)nonpolar
C)charged and polar
D)uncharged but polar
E)aprotic
Q4) Provide the structure of Thr-Gln-Met at pH 7.0.
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Chapter 23: Catalysis
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Q1) How does an acid catalyst increase the rate of reaction?
Q2) Describe the second step of a specific-base-catalyzed dehydration of a hydrate.
A)base abstracts a proton, electron pair from O-H bond goes to oxygen
B)negative charge from oxygen forms double bond, hydroxide departs as leaving group
C)base abstracts a proton, electron pair from O-H bond forms a double bond, hydroxide departs as leaving group
D)hydroxide departs as leaving group, then negative charge from oxygen forms a double bond
E)electron pair from O-H bond forms a double bond, base abstracts a proton
Q3) How does Zn<sup>2+</sup> catalyze the hydrolysis of trifluoroacetate esters?
Q4) Describe the acid-catalyzed second slow step in the hydrolysis of an ester.
A)The electron pair on oxygen forms double bond and alcohol is the leaving group.
B)The base abstracts extra hydrogen from protonated alcohol.
C)The oxygen of the carbonyl group abstracts a hydrogen from HB.
D)Water attacks the carbonyl carbon and electron pair goes to oxygen.
E)The oxygen on the alkoxy group abstracts a hydrogen from HB.
Q5) Explain the phenomenon known as molecular recognition. Give an example.
Q6) Explain what is meant by the induced fit model. Give an example.
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) Give the purpose of thymidylate synthase.
A)converts cytosine to guanine
B)converts guanine to cytosine
C)converts thymine to uracil
D)converts uracil to thymine
E)converts adenine to guanine
Q2) Which of the following reactions does the coenzyme biotin catalyze?
A)decarboxylation of an -keto acid
B)decarboxylation of an -carboxy acid
C)carboxylation of an -carboxy acid
D)decarboxylation of a carbon adjacent to an ester or keto group
E)carboxylation of a carbon adjacent to an ester or keto group
Q3) Which of the following statements regarding glycolysis is correct?
A)Glycolysis is another name for the Krebs cycle.
B)Disaccharides can enter glycolysis without being hydrolyzed.
C)Glycolysis occurs primarily in the fluid outside the cell.
D)Glycolysis is the series of reactions which produces 2 moles of pyruvate from each mole of D-glucose.
E)Glycolysis is the series of reactions which is responsible for the complete oxidation of pyruvate and acetyl-CoA to carbon dioxide.
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Chapter 25: The Chemistry of Metabolism
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Q1) Of the following compounds, which are generated in any step of the glycolytic conversion of glucose to pyruvate: ATP, ADP, NAD<sup>+</sup>, NADH, FAD, FADH<sub>2</sub>, acetyl-CoA.
Q2) What organic compound is the most important form of chemical energy?
Q3) Give the product from the beta-oxidation of a fatty acyl-CoA.
Q4) Give the product(s)formed from the hydrolysis of a fat.
A)esters
B)aldehydes
C)glycerol
D)fatty acids
E)ketones
Q5) Of the following compounds, which are consumed in any step of the glycolytic conversion of glucose to pyruvate: ATP, ADP, NAD<sup>+</sup>, NADH, FAD, FADH<sub>2</sub>, Acetyl-CoA.
Q6) In which stage of catabolism is the citric acid cycle found?
Q7) To what reaction are many endergonic metabolic processes coupled in order to make them exergonic?
Q8) Describe what's happening mechanistically when glucose reacts with ATP to yield glucose-6-phosphate.
Page 27
Q9) Provide the structure of -farnesene, a simple, acyclic sesquiterpene.
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Chapter 26: Nucleosides, Nucleotides, and 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) Which of the following statements best explains the source of energy behind the ATP molecule?
A)the energy released when a phosphoanhydride bond of ATP is broken
B)the energy released when adenosine binds to the phosphate
C)the energy released when ribose binds to the phosphate
D)the energy released when adenine binds to ribose
E)the energy released when ATP is reduced
Q3) Which of the following statements explains what nucleic acids are?
A)They are acidic in nature.
B)They are the carriers of genetic information.
C)DNA and RNA are collectively known as nucleic acids.
D)Nucleic acids are chains of five-membered ring sugars, each bonded to a heterocyclic amine, linked by phosphate groups.
E)all of the above
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Chapter 27: Synthetic Polymers
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Q1) A substituted ethylene polymer in which the substituents are randomly oriented is called ________.
A)a ditactic polymer
B)an eutatic polymer
C)an isotactic polymer
D)a syndiotatic polymer
E)an atactic polymer
Q2) Show the reaction which occurs when benzoyl peroxide is heated.
Q3) What are common factors that enter into the choice of radical initiators for chain-growth polymerization?
Q4) Which is not typically made through radical polymerization?
A)poly(styrene)
B)PVC
C)Dacron
D)poly(vinyl acetate)
E)Lucite
Q5) What is the mass of each repeating unit in poly(ethylene)?
Q6) Provide the structure of the monomer from which Orlon [poly(acrylonitrile)] is prepared.
Q7) List the three phases in the mechanism of chain-growth polymerization.
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Chapter 28: Pericyclic Reactions
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Q1) Under thermal conditions, (2E,4E)-hexadiene undergoes a ________ ring closure to yield ________.
A)conrotatory, cis-3,4-dimethylcyclobutene
B)conrotatory, trans-3,4-dimethylcyclobutene
C)disrotatory, cis-3,4-dimethylcyclobutene
D)disrotatory, trans-3,4-dimethylcyclobutene
Q2) Which of the following molecular orbitals are formed from subtractive overlap of atomic orbitals?
A)antibonding orbitals
B)out-of-phase orbitals
C)bonding orbitals
D)A and B
E)B and C
Q3) Which of the following molecular orbitals is produced when in-phase atomic orbitals overlap?
A)a bonding molecular orbital
B)an antibonding molecular orbital
C)a nonbonding molecular orbital
D)an out-of-phase molecular orbital
E)an excited energy state of molecular orbital
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