Advanced Organic Chemistry
Midterm Exam
Course Introduction
Advanced Organic Chemistry delves into the theoretical principles and practical applications underpinning the reactivity, synthesis, and mechanisms of organic molecules. This course explores contemporary topics such as pericyclic reactions, organometallic chemistry, stereoselectivity, and catalysis, alongside a detailed analysis of spectroscopic methods for structure elucidation. Emphasis is placed on current literature, retrosynthetic analysis, and strategic problem-solving, preparing students to tackle complex synthetic challenges and engage with cutting-edge research in organic chemistry.
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) Draw the Kekulé structure and show the direction of the dipole moment for CH<sub>2</sub>Cl<sub>2</sub>.
Answer: 11ea8a1c_2c6d_9d7f_b657_6dc2fcc50c70_TB1831_00
Q2) Which of the following molecules does not exhibit a net dipole moment of zero?
A)CO<sub>2</sub>
B)CH<sub>4</sub>
C)CCl<sub>4</sub>
D)H<sub>2</sub>O
E)SO<sub>3</sub>
Answer: D
Q3) Consider the interaction of two hydrogen 1s atomic orbitals of the same phase.Which of the statements below is an incorrect description of this interaction?
A)A sigma bonding molecular orbital is formed.
B)The molecular orbital formed is lower in energy than a hydrogen 1s atomic orbital.
C)The molecular orbital formed has a node between the atoms.
D)The molecular orbital formed is cylindrically symmetric.
E)A maximum of two electrons may occupy the molecular orbital formed.
Answer: C
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) Explain why AlCl<sub>3</sub> is a Lewis acid.
Answer: A Lewis acid is an electron pair acceptor.Aluminum in AlCl<sub>3</sub> has an empty p orbital that can accommodate the pair of electrons provided by a Lewis base.
Q2) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
Q3) 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.
Q4) HCN has a pKa = 9.1.What form of the compound,HCN or CN<sup>-</sup>,will predominate in a solution of pH = 7.0
Answer: HCN
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Chapter 3: An Introduction to Organic Compounds:
Nomenclature, physical Properties, and Structure
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Sample Questions
Q1) Identify the compound with the highest boiling point. A)CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub> B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH
C)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Cl
E)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br
Answer: B
Q2) Which of the following is the most soluble in H<sub>2</sub>O?
A)CH<sub>3</sub>OCH<sub>3</sub> B)CH<sub>3</sub>CH<sub>2</sub>OH
C)CH<sub>3</sub>CH<sub>2</sub>Cl
D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> E)CH<sub>3</sub>CHO
Answer: B
Q3) Draw the most stable conformer of trans-1-ethyl-4-methylcyclohexane.
Answer: 11ea8a1c_2c7f_7841_b657_413b90f767c1_TB1831_00
Q4) Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030c_b657_0556aed4dd3f_TB1831_00
Q5) Provide a representation of the gauche conformer of butane.
Answer: 11ea8a1c_2c7c_e01f_b657_85c913eea087_TB1831_00
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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) Provide the structure of (R)-4-octanol.Be careful to indicate proper stereochemistry.
Q4) Draw the structure of (2R,3S)-dichloropentane.Take particular care to indicate three-dimensional stereochemistry detail properly.
Q5) 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
Q6) Provide a careful structure for (2S,3R)-2,3-dibromohexane.
Q7) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
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Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) Under what conditions is G° equal to H° for a chemical reaction?
Q2) The rate determining step of a reaction is the
A)slowest step and thus,has highest energy barrier
B)slowest step and thus,has lowest energy barrier
C)fastest step and thus,has highest energy barrier
D)fastest step and thus,has lowest energy barrier
E)none of the above
Q3) Draw vinyl bromide.
Q4) Give the hybridization,shape,and bond angle for a carbon in ethene.
Q5) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms,one ring,and one bond?
Q6) Draw the structure of (Z)-1-chloro-2-methyl-2-butene.
Q7) What is the free energy of activation of a one-step reaction? How is it qualitatively related to the rate constant of the reaction?
Q8) Draw the structure of two alkenes with molecular formula C<sub>4</sub>H<sub>8</sub> that do not exhibit cis-trans isomerism.
Q9) Draw the structure of propyl vinyl ether.
Q10) Draw and name the six alkenes which have the molecular formula Page 7
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Chapter 6: The Reactions of Alkenes - the Stereochemistry of Addition
Reactions
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Q1) Identify the true statements in the mechanism in the addition of water to an alkene.
A)The addition of the electrophile is a slow step.
B)The addition of the nucleophile is a fast step.
C)A carbocation is formed as an intermediate.
D)Water abstracts the extra proton from the protonated alcohol.
E)all of the above
Q2) Upon hydrogenation,which of the following alkenes releases the least heat per mole?
A)3,4-dimethyl-1-hexene
B)(Z)-3,4-dimethyl-2-hexene
C)(E)-3,4-dimethyl-2-hexene
D)(Z)-3,4-dimethyl-3-hexene
E)(E)-3,4-dimethyl-3-hexene
Q3) What is the product of the hydrogenation of an alkene?
A)dihaloalkane
B)alkane
C)haloalkane
D)alcohol
E)ether
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
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Q1) Which of the following compounds is the major product when 1-hexyne is treated with excess HBr?
A)1,1-dibromohexane
B)1,1-dibromohexene
C)1,2-dibromohexene
D)1,2-dibromohexane
E)2,2-dibromohexane
Q2) Provide the structure of all distinct terminal alkynes with a molecular formula of C<sub>6</sub>H<sub>10</sub>.
Q3) Although you might expect 1-propyne to be more reactive than 1-propene in electrophilic addition reactions,the reverse is true.Explain this using your knowledge of the mechanism of electrophilic additions to both alkynes and alkenes.
Q4) The carbon-carbon triple bond of an alkyne is composed of A)three bonds.
B)two bonds and one bond. C)one bond and two bonds. D)three bonds.
Q5) Why are terminal alkynes more acidic than other hydrocarbons?
Q6) Provide the structure of (2E,4E)-2-chloro-2,4-octadiene.
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Electronic Effects: an Introduction to the Reactions of
Benzene
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Q1) What descriptive term is applied to the type of diene represented by 1,5-octadiene?
A)conjugated diene
B)cumulated diene
C)isolated diene
D)alkynyl diene
E)none of the above
Q2) Draw the LUMO of 1,3,5-hexatriene.
Q3) Stabilization of a charged species usually happens when this species can be more accurately depicted as a hybrid of several resonance contributing forms.Why is this the case?
Q4) Why does the (E,E)-isomer of 2,4-hexadiene react much more rapidly with dienophiles than does the (Z,Z)-isomer?
Q5) Rank the following dienes in order of increasing stability: trans-1,3-pentadiene,cis-1,3-pentadiene,1,4-pentadiene,and 1,2-pentadiene.
Page 11
Q6) When cycloheptatriene is deprotonated,an anion with seven resonance forms of equal energy can be drawn.Given this fact,explain why cycloheptatriene is only slightly more acidic than propene.
Q7) Provide the structure of indole.
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Page 12
Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Sample Questions
Q1) Identify the halide(s)that react in a S<sub>N</sub>2 reaction.You may choose more than one answer.
A)benzyl bromide
B)bromobenzene
C)1-bromo-1-butene
D)1-bromo-2-butene
E)2-bromo-2-phenylpropane
Q2) Which of the following correctly describes SAM,a biological methylating agent?
A)It contains a Cl bonded to a 1° carbon.
B)It contains a methyl group bonded to a positively charged sulfur atom.
C)It contains a methyl ether.
D)it contains a methyl group bonded to an aromatic ring.
E)It contains a Br bonded to a phosphorus atom.
Q3) 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]
Q4) Why,in a polar protic solvent,is iodide a better nucleophile than fluoride?
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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 is the strongest acid?
A)CH<sub>3</sub>NH<sub>2</sub>
B)CH<sub>3</sub>OH
C)CH<sub>3</sub>SH
D)CH<sub>3</sub>OCH<sub>3</sub>
E)CH<sub>3</sub>Cl
Q2) Which of the following is the best method for preparing CH<sub>3</sub>Br?
A)CH<sub>3</sub>OH + Br<sup>-</sup>
B)CH<sub>3</sub>OH + HBr
C)CH<sub>3</sub>OH + Br<sub>2</sub>
D)CH<sub>3</sub>OH + NaBr
E)CH<sub>3</sub>OH + Br<sup>+</sup>
Q3) When (R)-2-butanol is treated with TsCl in pyridine,the product formed is
A)an achiral compound
B)a mixture of diastereomers
C)a racemic mixture
D)a single enantiomer
E)none of the above
Q4) Draw the tosylate ion and explain why it is a particularly good leaving group.
Page 14
Q5) How are certain arene oxides believed to cause cancer?
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Chapter 11: Organometallic Compounds
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Sample Questions
Q1) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q2) List the sequence of reagents necessary to prepare the appropriate Gilman reagent from ethyl iodide.
Q3) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + CdCl<sub>2</sub>
Q4) What type of intermediate is present when the Grubbs catalyst and a terminal alkene react?
A)metallocyclobutane
B)Grignard reagent
C)Gilman reagent
D)borate ester
E)permanganate ester
Q5) Grubbs catalysts are based on A)palladium. B)copper.
C)magnesium. D)lithium. E)ruthenium.
Q6) Name the organic products that would result from metathesis of 1,8-nonadiene.
Page 15
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Chapter 12: Radicals
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Sample Questions
Q1) How would you convert 1-butene to 1-hexanol?
Q2) Provide the structure of semiquinone radical.
Q3) What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?
Q4) Name the two brominated products which result when 2,3-dimethyl-2-butene reacts with NBS.
Q5) Species with unpaired electrons are called ________.
Q6) Which of the following is true about the halogenation of methane,CH<sub>4</sub>?
A)The activation energy for F + CH<sub>4</sub> CH<sub>3</sub> + HF is larger than any other halogen.
B)O<sub>2</sub> slows these reactions by inhibiting the termination step.
C)The activation energy for I + CH<sub>4</sub> CH<sub>3</sub> + HI is relatively small.
D)The reaction must take place in the liquid state.
E)I<sub>2</sub> is unreactive because the activation energy for I + CH<sub>4</sub> CH<sub>3</sub> + HI is relatively large.
Q7) Show the propagating steps in the addition of HBr to 1-pentene in the presence of peroxide.
Q8) How would you convert 1-butene to 1-butanol using radical chemistry?
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Sample Questions
Q1) Which compound would be expected to show intense IR absorption at 1746 cm<sup>-1</sup>?
A)CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub> B)CH<sub>3</sub>CO<sub>2</sub>CH<sub>3</sub> C)CH<sub>3</sub>CH<sub>2</sub>CCH
D)CH<sub>3</sub>CH<sub>2</sub>SCH<sub>3</sub>
Q2) Which region of the electromagnetic spectrum,radio or visible,is characterized by waves of shorter wavelength?
Q3) Does the position of the stretch of the oxygen-hydrogen bond in alcohols depend on the concentration of the alcohol?
Q4) The mass spectrum of an unknown compound has a molecular ion peak with a relative abundance of 43.27% and an M + 1 peak with a relative abundance of 3.81%.How many carbon atoms are in the compound?
Q5) Which compound's C C IR band is weakest,1-butyne,2-pentyne,or 3-hexyne? Why?
Q6) A compound shows a molecular ion peak at m/z 167.The relative intensities of the M and M+1 peaks are 50.0 and 4.4 respectively.How many carbons are in each molecule of the compound?
Page 17
Q7) Which region of the electromagnetic spectrum,IR or X-ray,is characterized by waves of lower frequency?
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Chapter 14: Nmr Spectroscopy
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Sample Questions
Q1) Deduce the identity of the following compound from the spectral data given. C<sub>5</sub>H<sub>10</sub>O: <sup>1</sup>H NMR, 1.2 (6H,doublet),2.1 (3H,singlet),2.8 (1H,septet); IR,2980,1710 cm<sup>-1</sup>; MS,m/z 71,
Q2) Deduce the identity of the following compound from the spectral data given. C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>: <sup>1</sup>H NMR, 1.23 (3H,triplet),2.00 (3H,singlet),4.02 (2H,quartet); IR,2980,1740 cm-1
Q3) Determine the number of signals for isopentylamine in the <sup>1</sup>H NMR spectrum.
A)2
B)3
C)4
D)5
E)6
Q4) Deduce the structure from the data given: C<sub>7</sub>H<sub>16</sub>O; <sup>1</sup>H NMR (integration,coupling): 0.9 (9H,s),1.5 (2H,t),3.5 (3H,s),3.8 (2H,t).
Q5) ________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned =0 in <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy.
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Page 18
Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Q1) The hydrolysis of esters in base is called
A)the Fischer esterification.
B)the Hunsdiecker reaction.
C)the Dieckmann condensation.
D)transesterification.
E)saponification.
Q2) What reagents are used to dehydrate amides to nitriles?
Q3) What is the main intramolecular force between two molecules of propanoic acid?
A)London dispersion forces
B)dipole-dipole interaction
C)hydrogen bonding
D)induced dipole interactions
E)none of the above
Q4) Provide the structure of the tetrahedral intermediate in the reaction of sodium methoxide with propanoyl chloride.
Q5) What are the products of the reaction of benzoic acid with thionyl chloride?
Q6) Why are -lactams,such as penicillins and cephalosporins,unusually reactive amides?
Q7) Provide a detailed,stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide. Page 19
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Page 20
Chapter 16: Reactions of Aldehydes and Ketones
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Q1) Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.
Q2) 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
Q3) 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>.
Q4) Which of the following alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?
A)1-pentanol
B)2-pentanol
C)3-pentanol
D)2-methyl-2-pentanol
E)3-methyl-3-pentanol
Q5) Provide the structure of the diethyl acetal of butanal.
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) In the Michael reaction,addition to the , -unsaturated carbonyl occurs in a
A)1,2-fashion
B)1,3-fashion
C)1,4-fashion
D)1,5-fashion
E)Diels-Alder reaction
Q3) Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.
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) Show how an enolate can add to a carbonyl.
Page 22
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.
Q2) Explain why direct nitration of aniline yields,among other products,m-nitroaniline.
Q3) Which of the following fails to produce benzoic acid when heated in the presence of acidic sodium dichromate?
A)1-phenylethanol
B)2-phenylethanol
C)2-phenylheptane
D)2-methyl-2-phenylheptane
E)1-phenylheptanol
Q4) 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
Q5) What is the principle of microscopic reversibility?
Page 23
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) Draw the structures of piperidine and morpholine and explain their relative basicities.
Q2) Which heterocyclic ring is present in heme?
A)pyrrole
B)purine
C)pyrimidine
D)pyridine
E)porphyrin
Q3) Which heterocyclic ring is present in cytosine DNA base?
A)pyrrole
B)purine
C)pyrimidine
D)porphyrin
E)pyridine
Q4) Draw 2-methylpyrrolidine.
Q5) What is the stereochemistry of the product in the acid hydrolysis of trans-2,3-epoxybutane?
Q6) 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.
Page 24
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) Epimers are essentially A)enantiomers.
B)diasteromers.
C)identical.
D)constitutional isomes. E)tautomers.
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) 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?
Q4) Draw the most stable chair conformer of D-glucose.
Page 25
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Which of the following amino acids has an aliphatic R group?
A)serine
B)cysteine
C)asparagine
D)tyrosine
E)leucine
Q2) Draw and name the amino acids which may be described as heterocyclic.
Q3) What is an amino acid analyzer?
Q4) Complete hydrolysis of a hexapeptide gives 2 Gly,Leu,Phe,Pro,and Tyr.Reaction of the peptide with phenylisothiocyanate gave the phenylthiohydantoin of Pro.Partial hydrolysis of the peptide gave the following fragments: Phe-Gly-Tyr,Gly-Phe-Gly,Pro-Leu-Gly,Leu-Gly-Phe.What is the structure of the peptide?
Q5) The sequence of amino acids and location of the disulfide bridges can be obtained from the
A)primary structure.
B)secondary structure.
C)tertiary structure.
D)ternary structure.
E)quaternary structure.
Q6) What is the net charge of arginine in a solution of pH 1.0?
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Q1) In the hydrolysis of methyl trifluoroacetate,give two purposes of the zinc catalyst.You may choose more than one answer.
A)increases the rate of the first step by providing a metal-bound hydroxide ion
B)increases the rate of the second step by decreasing the basicity of the leaving group
C)increases the rate of the second step by increasing the basicity of the leaving group
D)increases the rate of the first step by providing a metal-bound water molecule
E)increases the rate of the last step by replacing alkoxide with hydroxide
Q2) Describe the first step of a general-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 an acid catalyst increase the rate of reaction?
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Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
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Q1) Which type of vitamins,water-soluble or lipid-soluble,can cause overdose?
Q2) Which of the following statements is not true of coenzymes?
A)Coenzymes catalyze chemical reactions similar to enzymes.
B)Coenzymes may function as oxidizing and reducing agents.
C)Coenzymes play a variety of chemical roles exactly like those played by the amino acid side chains of enzymes.
D)Coenzymes may function as nucleophiles or strong bases needed in a reaction.
E)Coenzymes may function as activators needed in a reaction.
Q3) Which of the following vitamins can be synthesized by all mammals except humans and guinea pigs?
A)vitamin B<sub>12</sub>
B)riboflavin (B<sub>2</sub>)
C)vitamin C
D)thiamine (B<sub>1</sub>)
E)pyridoxine (B<sub>6</sub>)
Q4) What are the main structural and functional differences between NAD<sup>+</sup>/NADH and NADP<sup>+</sup>/NADPH?
Q5) What are holoenzymes and apoenzymes?
Q7) Explain what is meant by a nucleotide and give an example. Page 28
Q6) Through what enzymatic pathway is thymine biosynthesized?
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Chapter 24: The Organic Chemistry of the Metabolic Pathways
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Q1) Identify the seventh step of the citric acid cycle.
A)Citrate is converted to isocitrate.
B)Conjugate addition of water to the double bond of fumarate forms (S)-malate.
C)Acetyl-CoA reacts with oxaloacetate to form citrate.
D)FAD oxidizes succinate to fumarate.
E)The secondary alcohol of isocitrate is oxidized to a ketone by NAD<sup>+</sup> and the ketone loses CO<sub>2</sub>.
Q2) Which of the following is the allosteric activator of phosphofructokinase?
A)AMP
B)ADP
C)ATP
D)ADP and AMP
E)ADP,AMP and ATP
Q3) Fumarate is an intermediate in the citric acid cycle.Draw its structure.
Q4) What compounds are formed when a carboxylate is phosphorylated by the attack at the b-phosphorus of ATP?
Q5) Describe what's happening mechanistically when glucose reacts with ATP to yield glucose-6-phosphate.
Q6) Give the product from the beta-oxidation of a fatty acyl-CoA.
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Chapter 25: The Organic Chemistry of Lipids
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Q1) Which of the following statements is true about terpenes?
A)They are a class of lipids that can be isolated from plants.
B)They contain carbon atoms in multiples of five.
C)They are composed of isoprene units joined together in a head-to-tail fashion.
D)Tetraterpenes have 40 carbon atoms.
E)all of the above
Q2) Which of the following is not an intermediate in the biosynthesis of isopentenyl pyrophosphate?
A)hydroxymethylglutaryl-CoA
B)mevalonylphosphate
C)acetoacetyl-CoA
D)dimethylallyl phosphate
E)mevalonic acid
Q3) How many isoprene units are in a sesquiterpene? A)1
Q4) Provide the structure of -farnesene,a simple,acyclic sesquiterpene.
Page 31
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Chapter 26: The Chemistry of the Nucleic Acids
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Q1) Draw the structure of UDP.
Q2) During the synthesis of dUMP to dTMP,dihydrofolate is reduced to tetrahydrofolate by
A)NAPH
B)NADPH
C)FADH
D)NADH
E)ATP
Q3) Draw the deaminated product of adenine.
Q4) Draw the structure of guanosine.
Q5) All tRNAs have ________ at the 3'-end.
A)CCA
B)UUC
C)GCC
D)CAG
E)GGA
Q6) Draw the structure of uridine.
Q7) Assuming that the human genome with its 3 billion base pairs is entirely in a b-helix,how long is the DNA in a human cell?
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Q8) Name the two pyrimidine bases which serve as components in deoxyribonucleotides.
Chapter 27: Synthetic Polymers
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Q1) Show the mechanism for the formation of a segment of polystyrene containing two molecules of styrene and initiated by hydrogen peroxide.
Q2) Why is chain branching less common in anionic polymerization than in cationic polymerization?
Q3) Which of the following polymers is used in bullet-proof vests?
A)Nylon 66
B)Kevlar
C)Mylar
D)Lexan
E)Teflon
Q4) 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
Q5) Show the reaction which occurs when benzoyl peroxide is heated.
Q6) What is the mass of each repeating unit in poly(ethylene)?
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Chapter 28: Pericyclic Reactions
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Q1) How many electrons are present in the nonbonding molecular orbital of the allyl anion?
A)0
B)1
C)2
D)3
E)4
Q2) How many molecular orbitals are produced from the overlap of four p atomic orbitals?
A)2
B)8
C)4
D)16
E)1
Q3) 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.
Q4) Give a representation of the antibonding molecular orbital of the allyl anion.
Q5) Under thermal conditions,is an [8+2] cycloaddition suprafacial or antarafacial?
Page 34
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