Organic Chemistry I Test Bank
Course Introduction
Organic Chemistry I introduces students to the fundamental principles of organic chemistry, focusing on the structure, properties, and reactivity of carbon-containing compounds. Key topics include bonding, molecular structure, nomenclature, stereochemistry, and the mechanisms of organic reactions such as substitution and elimination. The course provides a foundation for understanding functional groups, reaction types, and the energetics behind transformations, equipping students with the skills needed to analyze and predict the outcomes of organic reactions. Applications to biological and industrial processes are discussed, preparing students for advanced study in chemistry, biology, medicine, and related fields.
Recommended Textbook
Organic Chemistry 8th Edition by Paula Yurkanis Bruice
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28 Chapters
3204 Verified Questions
3204 Flashcards
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Chapter 1: Remembering General Chemistry: Electronic
Structure and Bonding
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Sample Questions
Q1) Give the electronic configuration for Ca<sup>+2</sup>.
Answer: 1s<sup>2</sup>2s<sup>2</sup>2p<sup>6</sup>3s<sup>2</sup>3p<sup>6</sup>
Q2) Draw the structure of a molecule which contains only carbon and hydrogen atoms (only three of which are carbon)and in which two of the carbons are sp<sup>2</sup> hybridized and the other is sp hybridized.
Answer: H<sub>2</sub>C 11ea8a1c_2c6b_c8b5_b657_6103d91eaf4f_TB1831_00 C 11ea8a1c_2c6b_efc6_b657_6d7bd69a64e9_TB1831_00 CH<sub>2</sub>
Q3) Draw the Lewis structure for CH<sub>3</sub>N<sub>2</sub><sup>+</sup>.
Answer: 11ea8a1c_2c63_6437_b657_ad9742f6e368_TB1831_00
Q4) Nitrous oxide N<sub>2</sub>O,also known as laughing gas is often used in surgery and dentistry for its anesthetic and analgesic effects.Draw its Lewis structure? Answer: 11ea8a1c_2c6e_fd18_b657_477afb08cbdb_TB1831_00
Q5) Give the hybridization,shape,and bond angle for each carbon in CH<sub>3</sub>CN. Answer: CH<sub>3 </sub>- sp<sup>3</sup>,tetrahedral,109.5; C - sp,linear,180
Q6) 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
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) Identify the most acidic carboxylic acid.
A)ICH<sub>2</sub>COOH
B)BrCH<sub>2</sub>COOH
C)CH<sub>3</sub>COOH
D)FCH<sub>2</sub>COOH
E)ClCH<sub>2</sub>COOH
Answer: D
Q2) Which of the following is the strongest acid?
A)CH<sub>3</sub>OH
B)CH<sub>3</sub>OH<sub>2</sub><sup>+</sup>
C)H<sub>2</sub>N<sup>-</sup>
D)CH<sub>3</sub>NH<sub>2</sub>
E)CH<sub>3</sub>NH<sub>3</sub><sup>+</sup>
Answer: B
Q3) Write a completed equation for the acid-base pair shown below.
HCO<sub>2</sub>H + <sup>-</sup>NH<sub>2</sub>
Answer: HCO<sub>2</sub>H + <sup>-</sup>NH<sub>2</sub>
HCO<sub>2</sub><sup>-</sup> + NH<sub>3</sub>
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:
Nomenclature, physical Properties, and Structure
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Sample Questions
Q1) Which of the following is sec-butyl alcohol?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH B)CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>3</sub> C)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH D)(CH<sub>3</sub>)<sub>2</sub>CHOH
E)(CH<sub>3</sub>)<sub>2</sub>CHOCH<sub>3</sub> Answer: B
Q2) Which of the following compounds does not have the molecular formula C<sub>6</sub>H<sub>14</sub>O?
A)1-hexanol
B)2-hexanol
C)3-methyl-2-pentanol
D)3-methyl-3-pentanol
E)cyclohexanol
Answer: E
Q3) Draw an acceptable structure for 3-ethyl-3-methylhexane. Answer: 11ea8a1c_2c75_b3fa_b657_35b02181103c_TB1831_00
Q4) Provide the IUPAC name of the compound.
H<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH Answer: 4-amino-1-butanol
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) The specific rotation of (R)-(+)-glyceraldehyde is +8.7°.If a mixture of glyceraldehydes enantiomers is 80% S and 20% R,what is the specific rotation of the mixture?
Q2) Meso compounds
A)are chiral
B)have plane of symmetry
C)are optically inactive
D)are constitutional isomers
E)B and C
Q3) What type of isomers are CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub> and CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH?
A)constitutional
B)symmetrical
C)configurational
D)conformational
E)stereochemical
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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Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) Consider the one-step conversion of F to G.Given that the reaction is endergonic by 5 kcal/mol and that the energy difference between G and the transition state for the process is 15 kcal/mol,sketch a reaction-energy profile for this reaction.Make sure to show how the given energy differences are consistent with your sketch.
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) Which of the following contributes to make G° more negative?
A)use of a catalyst
B)a more positive H°
C)a more positive S°
D)a larger rate constant
E)none of the above
Q4) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.
Q5) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
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Chapter 6: The Reactions of Alkenes - the Stereochemistry of Addition
Reactions
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Sample Questions
Q1) For an endergonic reaction step,the Hammond postulate allows one to say that
A)the transition state of the step resembles the reactants of the step.
B)the transition state of the step resembles the products of the step.
C)the step is rate-determining since it has the smallest E<sub>a</sub>.
D)the reaction containing this step is overall first order.
E)the transition state is precisely symmetric with bond-breaking and bond-forming occurring to the same extent.
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) Give the types of products formed from the bromination and catalytic hydrogenation (using D<sub>2</sub>)of cyclohexene.
Q4) Based on the relative stabilities of the intermediates involved,explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.
Page 8
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep
Synthesis
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Sample Questions
Q1) Why are mercuric ions needed during the hydration of alkynes?
A)They catalyze the reaction by reacting with the alkyne and making it more nucleophilic.
B)They catalyze the reaction by reacting with the alkyne and making it more electrophilic.
C)They make alkynes more soluble in water.
D)They increase the rate of addition reaction.
E)B and D
Q2) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q3) Provide the structure of the major organic product that results when 2-butyne is treated with 1 equivalent of Br<sub>2</sub>.
Q4) Give the IUPAC name for HCCCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
Q5) 2-butyne has higher boiling point than 2-butene because
A)2-butyne has stronger hydrogen bonds
B)2-butyne has stronger dipole dipole interactions
C)2-butyne has stronger london dispersion forces
D)2-butyne has triple bond which is harder to break
E)2-butyne has fewer hydrogens
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Chapter
Electronic Effects: an Introduction to the Reactions of
Benzene
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Sample Questions
Q1) A dienophile with an electron withdrawing group is a better
A)nucleophile.
B)electrophile.
C)catalyst.
D)solvent.
E)none of the above.
Q2) Mark the most electron-rich carbon atom in the compound below with an asterisk.
Q3) Rank the following dienes in order of increasing stability: trans-1,3-pentadiene,cis-1,3-pentadiene,1,4-pentadiene,and 1,2-pentadiene.
Q4) The type of reaction that benzene undergoes with electrophiles is a(n)
A)addition reaction.
B)substitution reaction.
C)subtraction reaction.
D)multiplication reaction.
E)elimination reaction.
Q5) Draw the HOMO of 1,3,5-hexatriene.
Q6) Provide the structure of the biologically significant heterocycle purine. Page 10
Q7) Classify cyclopentadienyl cation as aromatic,antiaromatic,or nonaromatic.Assume planarity of the network.
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Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Sample Questions
Q1) 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
Q2) Which alkyl halide reacts the fastest in an E2 reaction?
A)2-chloro-2-methylbutane
B)1-chlorobutane
C)1-chloro-2-methylbutane
D)2-chlorobutane
E)chloromethane
Q3) Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.
Q4) 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
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Q5) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
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) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>CH<sub>2</sub>OH + HBr
Q3) How are certain arene oxides believed to cause cancer?
Q4) 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
Q5) Why are alcohols typically poor electrophiles?
Q6) Draw the tosylate ion and explain why it is a particularly good leaving group.
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Chapter 11: Organometallic Compounds
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Sample Questions
Q1) 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
Q2) List the sequence of reagents necessary to prepare the appropriate Gilman reagent from ethyl iodide.
Q3) Give the major organic product for the following reaction. CH<sub>3</sub>CH<sub>2</sub>BR + (CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>CuLi
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>C H<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>Cu
B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cu
C)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>C H<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cu
D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>C H<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>Li
E)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li
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Chapter 12: Radicals
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Sample Questions
Q1) An alkane with the molecular formula C<sub>5</sub>H<sub>10</sub> forms only one monochlorinated product when heated with Cl<sub>2</sub>/hv.Give the structure and the IUPAC name for this alkane.
Q2) Which of the halogens below undergoes free radical halogenation with ethane most rapidly?
A)fluorine
B)chlorine
C)iodine
D)bromine
E)pyridine
Q3) Devise methods by which (CH<sub>3</sub>)<sub>2</sub>CCH<sub>2</sub> could be synthesized from 2-methylpropane.
Q4) What C<sub>5</sub>H<sub>12</sub> isomer will give only a single monochlorination product?
Q5) What is the relative reactivity of 2° vs 1° hydrogens in the free radical bromination of n-butane if the ratio of 1-bromobutane to 2-bromobutane formed is 7:93?
Q6) Name the two brominated products which result when 2,3-dimethyl-2-butene reacts with NBS.
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Sample Questions
Q1) In the UV-visible spectrum of (E)-1,3,5-hexatriene,the lowest energy absorption corresponds to
A)a to * transition.
B)a to * transition.
C)a to * transition.
D)a to * transition.
E)a to transition.
Q2) Which region of the electromagnetic spectrum,radio or visible,is characterized by waves of shorter wavelength?
Q3) Deduce a possible structure for the compound with the IR absorptions below. C<sub>4</sub>H<sub>8</sub>O: 3000,2800,2715,1715 cm<sup>-1</sup>
Q4) 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>
Q5) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of 2-bromobutane.
Page 16
Q6) Which compound's C C IR band is weakest,1-butyne,2-pentyne,or 3-hexyne? Why?
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Chapter 14: Nmr Spectroscopy
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Sample Questions
Q1) An unknown compound,C<sub>3</sub>H<sub>5</sub>Cl<sub>3</sub>,gave the following proton NMR data:
Doublet at 1.70 ppm (3H)
Multiplet at 4.32 ppm (1H)
Doublet at 5.85 ppm (1H)
What is the structure of the compound?
Q2) Which of the following protons gives an NMR signal with the highest chemical shift value (farthest downfield)? (CH<sub>3</sub>)<sub>2</sub>CH-O-CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub > <sub> </sub>1 2 3 4 5 A)1 B)2 C)3 D)4 E)5
Q3) Deduce the identity of the following compound from the <sup>1</sup>H NMR spectral data given.
C<sub>9</sub>H<sub>10</sub>O<sub>2 </sub>: 2.2 (3H,singlet),5.0 (2H,singlet),7.2 (5H,multilet)(ppm)
Q4) What information does a HETCOR spectrum give?
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Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Sample Questions
Q1) Predict the major organic product of the reaction between N-methylbenzamide and sodium propanoate.
A)N-propylbenzamide
B)propyl benzoate
C)phenyl propanoate
D)benzoic propanoic anhydride
E)no reaction
Q2) Provide the proper IUPAC name for (CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CH(CN)CH<sub>3</s ub>.
Q3) Why are -lactams,such as penicillins and cephalosporins,unusually reactive amides?
Q4) List the following carboxylic acid derivatives in decreasing order of reactivity in nucleophilic acyl substitution reactions: acetic anhydride,methyl acetate,acetamide,acetyl chloride.
Q5) Carbonated beverages typically have pH's below 7.0.What acid is present which lowers the pH? Show the reaction by which it is formed.
Q7) What are the products of the reaction of benzoic acid with thionyl chloride? Page 19
Q6) Provide a detailed,stepwise mechanism for the reaction of propanoic anhydride with phenol.
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Page 20
Chapter 16: Reactions of Aldehydes and Ketones
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Q1) Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H<sub>2</sub>NOH.
Q2) Provide the proper IUPAC name for PhCH<sub>2</sub>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>2</sub>CHO.
Q3) In carbon NMR,the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about
A)20 ppm
B)40 ppm
C)60 ppm
D)120 ppm
E)200 ppm
Q4) Provide the major organic product of the reaction of aniline with 3-pentanone.
Q5) Provide the proper IUPAC name for CH<sub>3</sub>CHOHCH<sub>2</sub>COCH<sub>2</sub>C(CH<sub>3</sub>)<sub>2</ sub>CH<sub>2</sub>CH<sub>3</sub>.
Q6) List the following carbonyl compounds in order of decreasing reactivity toward nucleophiles: ester,acid chloride,amide,aldehyde,ketone.
Q7) Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.
Page 21
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Chapter 17: Reactions at the -Carbon
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Q1) Which of the following statements describes the first step in the mechanism of the aldol condensation?
A)An alpha hydrogen is abstracted by the base to form an enolate anion.
B)A nucleophilic base attacks the carbonyl carbon atom.
C)The carbonyl oxygen is protonated by the base ion.
D)The alpha hydrogen is abstracted by an acid to the enolate anion.
E)The carbonyl oxygen of one aldehyde attacks the carbonyl carbon of another.
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) Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.
Q4) 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?
Q5) How would you convert cyclohexene to 2-methylcyclohexanone?
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) Which of the following cannot serve as a Lewis acid in electrophilic aromatic substitution?
A)AlCl<sub>3</sub>
B)FeCl<sub>3</sub>
C)FeBr<sub>3</sub>
D)BBr<sub>3</sub>
E)NH<sub>3</sub>
Q2) Explain why direct nitration of aniline yields,among other products,m-nitroaniline.
Q3) The name 2,4,6-tribromobenzene is incorrect.Which of the following is the correct name?
A)tribromobenzene
B)m,m-dibromobromobenzene
C)3,5-dibromobromobenzene
D)1,3,5-tribromobenzene
E)m,m,m-tribromobenzene
Q4) Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO<sub>3</sub>/H<sub>2</sub>SO<sub>4</sub> to yield o-nitroacetophenone.Circle the resonance form which is less stable than the other two.
Page 23
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) Draw the structure of a porphyrin ring system,and list three common,naturally-occurring molecules which contain a porphyrin-like ring system as part of their structure.
Q2) Which of the following amino acids contain a heterocyclic ring?
A)tryptophan
B)proline
C)histidine
D)alanine
E)tryptophan,proline and histidine
Q3) 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
Q4) Provide the structure of thymine; How is it used by organisms?
Q5) Pyridine does not undergo Friedel-Crafts reactions.Offer an explanation.
Q6) Draw the structure of piperidine.
Q7) Draw 2-methylpyrrolidine.
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) What is the main structural difference between amylose and cellulose?
Q2) Which of the following statements best describes the difference between amylose and amylopectin?
A)Amylose is a branched polysaccharide while amylopectin is a chain polysaccharide.
B)Amylose is a straight-chain polysaccharide while amylopectin is a branched polysaccharide.
C)Amylose contains -1,6-glycosidic linkage which amylopectin does not contain.
D)Amylose is composed of thousands of D-glucose units while amylopectin is composed of thousands of D-galactose units.
E)Amylose is one of the largest molecules found in nature while amylopectin is one of the smallest molecules found in nature.
Q3) Why is -D-glucopyranose more stable in nature than -D-glucopyranose?
Q4) Draw the Haworth structure 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 the Haworth structure of -D-ribofuranose.
Q7) Draw the more stable chair conformer of -D-glucopyranose.
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Describe how electrophoresis works.
Q2) What is an amino acid analyzer?
Q3) Rank the following amino acids in order of time of elution from a cation-exchange resin and a buffer pH of 4.0: aspartic acid,phenylalanine,arginine,and alanine.
Q4) What is the major force responsible for the formation of an -helix in protein secondary structure?
Q5) Draw the structure of the tetrapeptide Ser-Leu-Phe-Pro at pH 7.0.
Q6) Which of the following amino acids has the highest isoelectric point?
A)arginine
B)aspartic acid
C)glycine
D)proline
E)phenylalanine
Q7) What are enzymes?
A)saccharides that catalyze chemical reactions
B)nucleic acids that catalyze chemical reactions
C)unsaturated fats that catalyze chemical reactions
D)DNA molecules that catalyze chemical reactions
E)proteins that catalyze chemical reactions
Page 26
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Q1) Why is histidine a versatile catalytic group?
Q2) Which of the following statements account for the remarkable catalytic ability of enzymes?
A)proper positioning and specificity of active site and substrate
B)proper positioning of amino acid side chains that serve as catalytic groups
C)ability of the groups on the enzyme to stabilize transition states
D)A and B
E)all of the above
Q3) Which of the following statements concerning general-acid catalysis is correct?
A)The proton is transferred to the reactant during the slow step of the reaction.
B)The transition state of the slow step of the reaction has a partially transferred proton instead of a fully transferred proton.
C)Typically,a general-acid catalyst is stronger than a specific-acid catalyst.
D)both A and B
E)all of the above
Q4) Explain what is meant by site-specific mutagenesis.
Q5) Explain why an intramolecular reaction resulting in the formation of five- or six-membered rings occurs more readily than the corresponding intermolecular reaction.
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Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
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Q1) 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
Q2) What is the first reaction in the catabolism of most amino acids?
A)transamination
B)decarboxylation
C)phosphorylation
D)aldolation
E)ligation
Q3) 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
Q4) What are holoenzymes and apoenzymes?
Q5) Explain what is meant by a nucleotide and give an example.
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Chapter 24: The Organic Chemistry of the Metabolic Pathways
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Q1) Most of the energy provided by chemical nutrients is provided in what stage of catabolism?
Q2) In glycolysis,each molecule of glucose is converted to two molecules of A)pyruvate.
B)acetaldehyde.
C)1,3-dihydroxyacetone.
D)acetyl-CoA.
E)glycerol.
Q3) 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.
Q4) The first reaction in the b-oxidation pathway produces
A)an a,b-unsaturated fatty acyl-CoA.
B)a b-hydroxy fatty acyl-CoA.
C)an a-hydroxy fatty acyl-CoA.
D)a b-keto fatty acyl-CoA.
E)an a-keto fatty acyl-CoA.
Q5) What chemical interactions allow certain enzymes to catalyze the hydrolysis of ATP?
Q6) What explains the kinetic stability of ATP in aqueous media at biological pH?
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Chapter 25: The Organic Chemistry of Lipids
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Sample Questions
Q1) 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.
Q2) Which of the following statements is true for both cholesterol and vitamin A?
A)Both are vitamins.
B)Both are proteins.
C)Both are lipids.
D)Both are steroids.
E)Both are fatty acids.
Q3) Why do most naturally occurring fatty acids contain an even number of carbon atoms?
Q4) Most hormones are A)phosphoglycerides.
B)terpenes.
C)squalenes.
D)prostaglandins.
E)steroids.
Q5) Provide the structure of -farnesene,a simple,acyclic sesquiterpene.
Q6) 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.
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Chapter 26: The Chemistry of the Nucleic Acids
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Sample Questions
Q1) Propose a mechanism for the formation of cyclic AMP from ATP.
Q2) Draw the structure of uridine.
Q3) How many billion base pairs are there in the total DNA of a human cell?
A)3
B)5
C)8
D)11
E)13
Q4) Identify the bonding in DNA between the nucleotides.
A)5' to 4'
B)5' to 3'
C)3' to 5'
D)4' to 3'
E)3' to 4'
Q5) What is the composition of a ribosome?
A)40% protein,60% rRNA
B)60% protein,40% tRNA
C)40% protein,60% tRNA
D)40% protein,60% mRNA
E)100% protein,0% rRNA
31
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Chapter 27: Synthetic Polymers
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Q1) Which of the following species can best serve as a radical initiator for radical polymerization?
A)ROH
B)ROR
C)ROOR
D)RCOOR
E)RCOOH
Q2) Which of the following polymers is used in bullet-proof vests?
A)Nylon 66
B)Kevlar
C)Mylar
D)Lexan
E)Teflon
Q3) The joining together of many monomers to form a very large molecule is called A)polymerization.
B)monomerization.
C)dimerization.
D)hydroxylation.
E)homogenization.
Q4) Show the reaction which occurs when benzoyl peroxide is heated.
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Chapter 28: Pericyclic Reactions
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Q1) What characterizes a pericyclic reaction?
Q2) 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
Q3) Under thermal conditions,(2E,4Z)-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
Q4) 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
Page 33
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