Medicinal Chemistry Test Preparation
Course Introduction
Medicinal Chemistry is a multidisciplinary scientific course that explores the design, synthesis, and development of pharmaceutical agents. It integrates principles from organic chemistry, biology, pharmacology, and computational sciences to understand how chemical structure relates to drug function and activity within the body. Students will learn about the processes involved in drug discovery, target identification, lead optimization, and the molecular mechanisms of drug action. The course also covers important topics such as structure-activity relationships (SAR), drug metabolism, pharmacokinetics, and strategies for optimizing the therapeutic efficacy and safety of medicinal compounds.
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 statements correctly describes the third electron shell that surrounds the nucleus of an atom?
A)The third shell contains only s and p atomic orbitals.
B)The maximum number of electrons that can occupy the third shell is 18.
C)The total number of atomic orbitals present in the third shell is 16.
D)The third shell can contain f orbitals.
E)All third shell elements must have d electrons.
Answer: B
Q2) The atomic number of boron is 5. The correct electronic configuration of boron is ________.
A)1s<sup>2 </sup>2s<sup>3</sup>
B)1s<sup>2 </sup>2p<sup>3</sup>
C)1s<sup>2 </sup>2s<sup>2 </sup>2p<sup>1</sup>
D)2s<sup>2 </sup>2p<sup>3</sup>
E)1s<sup>2 </sup>2s<sup>2 </sup>3s<sup>1</sup>
Answer: C
Q3) Atoms with the same number of protons but different numbers of neutrons are called ________.
Answer: isotopes
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) The conjugate acid of H<sub>2</sub>O is ________.
A)H<sub>3</sub>O<sup>-</sup>
B)H<sub>3</sub>O
C)H<sub>3</sub>O<sup>+</sup>
D)HO<sup>-</sup>
E)H<sub>2</sub>O<sup>+</sup>
Answer: C
Q2) Which of the following is not a conjugate acid-base pair?
A)"H<sub>2</sub>O, HO<sup>-</sup>"
B)"H<sub>2</sub>O, H<sub>3</sub>O<sup>+</sup>"
C)"HSO<sub>4</sub><sup>-</sup>, H<sub>2</sub>SO<sub>4</sub>"
D)"<sup>-</sup>OH, O<sup>2-</sup>"
E)"NO<sub>3</sub><sup>-</sup>, NO<sub>2</sub><sup>-</sup>"
Answer: E
Q3) Propanoic acid, CH<sub>3</sub>CH<sub>2</sub>COOH, has a pKa =4.9. Draw the structure of the conjugate base of propanoic acid and give the pH above which 90% of the compound will be in this conjugate base form.
Answer: CH<sub>3</sub>CH<sub>2</sub>COO<sup>-</sup>; 5.9
Q4) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
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Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) Draw the structure of N-ethyl-5-methyl-3-hexanamine.
Answer: 11ea7d6e_0665_7bc1_8568_5b2154bacfb6_TB1830_00_TB1830_00
Q2) If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?
A)n
B)n + 2
C)n - 2
D)2n
E)2n + 2
Answer: E
Q3) Assuming roughly equivalent molecular weights, which of the following would have the highest boiling point?
A)a tertiary amine
B)a quaternary ammonium salt
C)an alcohol
D)an ether
E)an alkyl chloride
Answer: B
Q4) Provide the chair structure of cis-decalin, two cis-fused six-membered rings.
Answer: 11ea7d6e_0669_9a97_8568_4b548fc8e6b9_TB1830_00_TB1830_00
Page 5
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) Draw the structure of (2S,3R)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.
Q2) 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?
Q3) (-)-Mandelic acid has a specific rotation of -158°. What would be the specific rotation of a solution which contains 40% (-)-mandelic acid and 60% (+)-mandelic acid?
A)+95°
B)+63°
C)+32°
D)-32°
E)-63°
Q4) Briefly describe how two enantiomers might be separated.
Q5) Twenty grams of a compound was dissolved in 100 mL of solvent and gave an observed rotation of -20 degrees. The sample tube is 4 dm long. Calculate the specific rotation.
Q6) Steroisomers which are not mirror image isomers are ________.
Q7) Draw the stereoisomers of 1,3-dichlorocyclopentane.
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Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.
Q2) An increase in which of the following results in a decrease in the rate of the chemical reaction?
A)temperature
B)concentration
C)collision frequency
D)energy of activation
E)fraction of collisions with proper orientation
Q3) Draw the structure of propyl vinyl ether.
Q4) Give the general formula for a cyclic alkene.
A)C<sub>n</sub>H<sub>2n-4</sub>
B)C<sub>n</sub>H<sub>2n-2</sub>
C)C<sub>n</sub>H<sub>2n</sub>
D)C<sub>n</sub>H<sub>2n+2</sub>
Q5) Draw the structure of two alkenes with molecular formula C<sub>4</sub>H<sub>8</sub> that do not exhibit cis-trans isomerism.
Q6) 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.
Page 7
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Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) Which statement is true in the oxymercuration-reduction 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)Markonikov orientation and both syn and anti addition occur.
Q2) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
Q3) Give the product for the reaction of 1-butene with methanol in the presence of acid.
A)1-ethoxybutane
B)2-ethoxybutane
C)1-methoxybutane
D)2-methoxybutane
E)1-butanol
Q4) Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclopentane as the major organic product.
Q5) What is hyperconjugation, and how does it affect carbocation stability?
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Chapter 7: Reactions of Alkynes Introduction to Multistep
Synthesis
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Sample Questions
Q1) 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.
Q2) Draw an acceptable structure for 3-sec-butyl-1-heptyne.
Q3) The reagent needed to convert 2-butyne to cis-2-butene is ________.
A)H<sub>2</sub>/Pt
B)H<sub>2</sub>/Lindlar's catalyst
C)Li/NH<sub>3</sub>
D)Na/NH<sub>3</sub>
E)H<sup>+</sup>/Zinc dust
Q4) Provide the structure of all distinct terminal alkynes with a molecular formula of C<sub>6</sub>H<sub>10</sub>.
Q5) In the reduction of alkynes using sodium in liquid ammonia, which of the species below is not an intermediate in the commonly accepted mechanism?
A)vinyl anion
B)vinyl radical
C)radical anion
D)vinyl cation
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 MOs are bonding MOs in the ground state of 1,3,5-hexatriene?
Q2) What is the hybridization of the central carbon of allene (1,2-propadiene)?
A)sp
B)sp<sup>2</sup>
C)sp<sup>3</sup>
D)p
E)none of the above
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) Among a series of isomeric trienes, the more negative the H° of the hydrogenation reaction of a given triene, the ________ stable it is relative to the others in the isomeric series.
Q5) 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
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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) 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
Q3) Which of the following is a secondary alkyl halide?
A)CH<sub>3</sub>Br
B)(CH<sub>3</sub>)<sub>3</sub>CBr
C)(CH<sub>3</sub>)<sub>2</sub>CHBr
D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>Br
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Sample Questions
Q1) What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is heated in ethanol?
Q2) List the following compounds in order of increasing reactivity in an E1 elimination. CH<sub>3</sub>CH<sub>2</sub>CHBrCH<sub>3</sub>, CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br, (CH<sub>3</sub>)<sub>3</sub>CBr
Q3) Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?
A)1-chloropentane
B)2-chloropentane
C)3-chloropentane
D)1-chloro-2-methylbutane
E)1-chloro-3-methylbutane
Q4) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
Q5) Which of the following alkyl chlorides would undergo substitution most rapidly when treated with NaCCH: chloroethane, 2-chloropropane, or 1-chloro-2,2-dimethylpropane?
Provide the structure of the substitution product.
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Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and
Sulfur-Containing Compounds
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Sample Questions
Q1) 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
Q2) 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
Q3) How are certain arene oxides believed to cause cancer?
Q4) 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.
Q5) Draw the tosylate ion and explain why it is a particularly good leaving group.
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Chapter 12: Organometallic Compounds
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Sample Questions
Q1) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q2) Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain briefly.
Q3) In a Grignard reagent, the carbon bonded to the magnesium has a partial ________ charge, because carbon is ________ electronegative than magnesium. This makes this carbon of the Grignard ________.
A)negative, more, nucleophilic
B)negative, less, electrophilic
C)positive, more, electrophilic
D)positive, less, nucleophilic
E)positive, less, electrophilic
Q4) List the sequence of reagents necessary to prepare the appropriate Gilman reagen from ethyl iodide.
Q5) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + CdCl<sub>2</sub>
Q6) 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?
Page 14
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) Write an equation to describe the initiation step in the chlorination of methane.
Q2) Name the two brominated products which result when 2,3-dimethyl-2-butene reacts with NBS.
Q3) Given the bond dissociation energies below (in kcal/mol), calculate the overall H° for the following reaction: (CH<sub>3</sub>)<sub>3</sub>CH + Br<sub>2</sub> (CH<sub>3</sub>)<sub>3</sub>CBr + HBr (CH<sub>3</sub>)<sub>3</sub>C-H 91 (CH<sub>3</sub>)<sub>3</sub>C-Br 65
Br-Br 46
H-Br 88
CH<sub>3</sub>-Br 70
Q4) What C<sub>5</sub>H<sub>12</sub> isomer will give only a single monochlorination product?
Q5) Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-2-heptene.
Q6) What role do vitamins C and E play in biological radical reactions?
Q7) Explain how CFCs are linked to depletion of stratospheric ozone.
Page 15
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) Which of the following is not a major peak in the MS of isopentane?
A)29
B)43
C)57
D)60
E)72
Q2) Which of the following statements is not true about electromagnetic radiation?
A)The velocity of light is directly proportional to the energy.
B)All molecules absorb electromagnetic radiation at some frequency.
C)Frequency is inversely proportional to wavelength.
D)Energy is directly proportional to frequency.
E)Energy is inversely proportional to wavelength.
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) Describe the similarities and differences in the infrared spectra of methyl propanoate and butanoic acid.
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Chapter 15: Nmr Spectroscopy
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Sample Questions
Q1) Provide the structure that is consistent with the data below. C<sub>5</sub>H<sub>10</sub>O<sub>2</sub> IR (cm<sup>-1</sup>): 2950, 1720 <sup>1</sup>H NMR ( ): 3.6 (s, 3H), 2.5 (septet, 1H), 0.9 (d, 6H) <sup>13</sup>C NMR ( ): 190 (s), 55 (q), 40 (d), 16 (q)
Q2) Give one reason why <sup>13</sup>C NMR is less sensitive than <sup>1</sup>H NMR.
Q3) How might the proton spectrum of ultrapure dimethylamine, (CH<sub>3</sub>)<sub>2</sub>NH, differ from the spectrum of this compound to which D<sub>2</sub>O has been added?
Q4) What type of 2-D NMR spectrum indicates which carbon atoms are coupled to which hydrogen atoms?
A)DEPT
B)APT
C)COSY
D)HETCOR
E)MRI
Q5) What information does a COSY spectrum give?
Q6) Can alkenes and aromatics be easily distinguished from each other in an <sup>13</sup>C NMR spectrum?
Page 17
Q7) Why is carbon-hydrogen coupling not generally seen in <sup>1</sup>H NMR spectra?
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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Sample Questions
Q1) What are the major organic products when 1 equivalent of acetic formic anhydride reacts with 1 equivalent of methanol?
Q2) Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with methanol to produce methyl acetate and HCl.
Q3) Give a detailed, stepwise mechanism for the Fischer esterification of acetic acid with methanol.
Q4) Which of the following esters undergoes hydrolysis in base most easily?
A)CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>
B)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>
C)C<sub>6</sub>H<sub>5</sub>O<sub>2</sub>CCH<sub>3</sub>
D)p-CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>CCH<sub>3</sub>
E)p-NO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>CCH<sub>3</sub>
Q5) What is the hybridization and geometry of the carbonyl carbon in carboxylic acids and their derivatives?
A)sp<sup>3</sup>, tetrahedral
B)sp<sup>2</sup>, trigonal planar
C)sp<sup>2</sup>, tetrahedral
D)sp<sup>3</sup>, trigonal planar
E)sp, trigonal planar
Page 18
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Chapter 17: Reactions of Aldehydes and Ketones
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Sample Questions
Q1) By which single-step process can benzene be readily converted into acetophenone?
Q2) When HOCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>COCH<sub>2</sub >CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH is heated in the presence of an acid catalyst, a reaction occurs. The product has the formula C<sub>9</sub>H<sub>16</sub>O<sub>2</sub>. Provide the structure of this product.
Q3) Which of the following synthetic routes works best for preparing 4-octene?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH=PPh<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
B)4-bromooctane + NaOCH<sub>3</sub>
C)4-bromooctane + KOC(CH<sub>3</sub>)<sub>3</sub>
D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
E)CH<sub>3</sub>CH<sub>2</sub>CH=PPh<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
Q4) Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH<sub>2</sub>CH<sub>2</sub>OH)to produce an acetal.
Q5) Propose a synthesis of 4-phenyl-2-butanol from 3-phenylpropanal.
Q6) Propose a synthesis of 3-methyl-4-heptyn-3-ol from 1-butyne.
Page 19
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Sample Questions
Q1) Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.
Q2) Which of the following will alkylate a lithium enolate most rapidly?
A)methyl bromide
B)isopropyl bromide
C)neopentyl bromide
D)bromobenzene
E)2-methylbromobenzene
Q3) Enolates are frequently formed by treating an aldehyde or ketone with LDA. However, the LDA must first be generated by reacting diisopropylamine with butyllithium. Why don't chemists just use butyllithium itself to deprotonate the aldehyde or ketone and form the enolate?
Q4) In theory a poorly planned crossed aldol reaction can produce how many different aldol regioisomers?
Page 20
Q5) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Q1) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.
Q2) What is the major organic product that results when benzene is treated with 1-chlorobutane and AlCl<sub>3</sub>?
A)ethylbenzene
B)isobutylbenzene
C)butylbenzene
D)sec-butylbenzene
Q3) Name the major organic product which results when 4-ethylbenzenesulfonic acid is heated in aqueous acid.
Q4) Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.
Q5) Can one distinguish among the three isomeric xylenes using <sup>13</sup>C NMR? Explain.
Q6) Provide the structure of benzenesulfonic acid.
Q7) Provide the structure of anisole.
Q8) What is the best method for the preparation of p-chlorotoluene in high yield?
A)start with benzene; methylate; chlorinate
Page 21
B)start with benzene; chlorinate; methylate
C)start with toluene; chlorinate
D)start with chlorobenzene; methylate
E)start with p-aminotoluene; NaNO<sub>2</sub>/HCl, 0°C; CuCl
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Page 22
Chapter 20: More About Amines Heterocylic Compounds
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Q1) Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.
Q2) Draw the structures of piperidine and morpholine and explain their relative basicities.
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) Which of the following chloropyridines readily undergo nucleophilic substitution upon treatment with NaCN?
A)2-chloropyridine
B)3-chloropyridine
C)4-chloropyridine
D)both A and B
E)both A and C
Q5) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
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Chapter 21: Carbohydrates
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Q1) Is L-glucose the enantiomer of D-glucose, the C-5 epimer of D-glucose, or both?
Q2) Under what conditions is the methyl glycoside of galactose prepared?
Q3) Which of the following best represents the process of photosynthesis?
A)disproportionation
B)oxidation/reduction
C)exothermic
D)exergonic
E)elimination
Q4) Which of the following statements best describes the main structural difference between cellulose and chitin?
A)The C-2 carbon in chitin contains an N-acetyl amino group instead of an OH group.
B)The C-2 carbon in cellulose contains an N-acetyl amino group instead of an OH group.
C)Chitin is a -1,4-glycosidic linkage while cellulose is a -1,4-glycosidic linkage.
D)Chitin is a -1,4-glycosidic linkage while cellulose is a -1,4-glycosidic linkage.
E)Chitin is a branched polysaccharide while cellulose is a chain polysaccharide.
Q5) Draw the Fischer projection for the open-chain form of D-fructose.
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) In nature, which is the most commonly found isomer, L-amino acids or D-amino acids?
Q2) Provide the structure of the tripeptide val-gly-ser at biological pH.
Q3) When a disulfide linkage is formed, the compound containing this new linkage has been ________.
A)hydrolyzed
B)dehydrated
C)electrolyzed
D)oxidized
E)reduced
Q4) Draw the form of L-lysine which is present at biological pH.
Q5) Provide the structure of the tripeptide val-gly-ser at pH 12.
Q6) What amino acid can be obtained by the reductive amination of -ketoglutaric acid, HO<sub>2</sub>CCH<sub>2</sub>CH<sub>2</sub>COCO<sub>2</sub>H?
A)glycine
B)serine
C)lysine
D)aspartic acid
E)glutamic acid
Page 25
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Chapter 23: Catalysis
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Q1) Which of the following residues are found at the active site of lysozyme?
A)His 57, Asp 102
B)His 57, Asp 52
C)Glu 35, His 57
D)Asp 102, Glu 35
E)Glu 35, Asp 52
Q2) What does the model termed "lock-and-key" stand for?
A)The hydrogen bonds in the -helix fit each other like a key fits a lock.
B)The amino acids in a peptide chain fit each other like a key fits a lock.
C)The substrate fits the active site of the enzyme like a key fits a lock.
D)The nonpolar sites of proteins fit each other like a key fits a lock.
E)The N-terminal and the C-terminal ends of a protein fit each other like a key fits a lock.
Q3) 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.
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) 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.
Q2) Through what enzymatic pathway is thymine biosynthesized?
Q3) Show the transimination (trans-Schiffization)reaction that happens in all PLP-requiring enzymes in which the amino acid substrate forms a Schiff base with PLP, thereby freeing the lysine side chain.
Q4) What structural feature of enzymes that catalyze redox reactions requires the presence of a coenzyme for reaction to occur?
Q5) Explain why a cell typically maintains its [NAD<sup>+</sup>]/[NADH] ratio near 1000 while keeping its [NADP<sup>+</sup>]/[NADPH] ratio at about 0.01.
Q6) What are holoenzymes and apoenzymes?
Q7) Which type of vitamins, water-soluble or lipid-soluble, can cause overdose?
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Chapter 25: The Chemistry of Metabolism
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Q1) 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
Q2) Draw the structure of pyruvate.
Q3) In the citric acid cycle, the acetyl group of each molecule of acetyl-CoA is converted into two molecules of ________.
A)carbon dioxide
B)oxygen
C)acetone
D)acetaldehyde
E)ethanol
Q4) What explains the kinetic stability of ATP in aqueous media at biological pH?
Q5) Causing a burning sensation in the muscles, what compound builds up in muscle cells when glycolysis occurs under anaerobic conditions?
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) What are the four common ribonucleosides?
Q2) 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.
Q3) Draw the structure of UDP.
Q4) What is meant by semiconservative DNA replication?
Q5) Draw the structure of cytidine 5'-phosphate.
Q6) What are antigene and antisense agents?
Q7) Draw the structure of TTP.
Q8) What are stacking interactions in DNA and what purpose do they serve?
Q9) Show that you understand how the structural components of DNA are bonded together by drawing a linear segment that contains 3 base residues.
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Q10) Show the hydrogen bonding which occurs when adenine and thymine form a base pair.
Chapter 27: Synthetic Polymers
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Q1) Which of the following statements best describes what vulcanization means?
A)a process by which rigid and non-sticky rubber can be made soft and sticky
B)a chemical process discovered by Charles Schultz in 1944
C)the heating of rubber with sulfur
D)a chemical process that destroys cross-linking in rubber
E)all of the above
Q2) List the three phases in the mechanism of chain-growth polymerization.
Q3) Which of the following are characteristics of thermosetting polymers?
A)strong and rigid
B)high degree of cross-linking
C)can be remelted by heating
D)A and B
E)A, B, and C
Q4) The pattern below is found in what type of polymer? AAAABBBBAAAABBBB
A)an alternating copolymer
B)a block copolymer
C)a random copolymer
D)a graft copolymer
E)a homopolymer
Q5) Name the monomer used in the production of neoprene.
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Chapter 28: Pericyclic Reactions
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Q1) Give a representation of the bonding molecular orbital of the allyl cation.
Q2) Under what conditions would a 1,3-hydrogen shift occur in a sigmatropic rearrangement?
A)thermal conditions
B)photochemical conditions
C)suprafacial pathway
D)A and C
E)B and C
Q3) Which of the following reactions best describes the Diels-Alder reaction?
A)electrocyclic reaction
B)cycloaddition reaction
C)sigmatropic reaction
D)radical reaction
E)nucleophilic substitution reaction
Q4) Give a representation of the antibonding molecular orbital of the allyl anion.
Q5) What is meant by frontier orbitals?
Q6) What does LCAO stand for?
Q7) Under photochemical conditions, is an [2+2] cycloaddition suprafacial or antarafacial?
Q8) Explain what a node is and how it is formed.
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