Organic Chemistry I
Exam Answer Key
Course Introduction
Organic Chemistry I is an introductory course that explores the fundamental principles and concepts of organic chemistry, focusing on the structure, properties, and reactivity of carbon-based molecules. Topics covered include bonding and molecular structure, nomenclature, stereochemistry, reaction mechanisms, and the synthesis and reactions of major functional groups such as alkanes, alkenes, alkynes, and alkyl halides. Emphasis is placed on understanding how molecular structure influences physical and chemical behavior, developing problem-solving skills, and applying foundational knowledge to a variety of biochemical and pharmaceutical contexts. This course serves as a critical prerequisite for advanced studies in chemistry, biology, and related disciplines.
Recommended Textbook
Organic Chemistry 8th 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) Give the hybridization,shape,and bond angle for the carbon in CO<sub>2</sub>.
Answer: sp,linear,180
Q2) Identify the compound with the weakest bond.
A)H<sub>2</sub>
B)HF
C)HCl
D)HBr
E)HI
Answer: E
Q3) Which of the following elements does this electronic configuration represent? 1s<sup>2</sup> 2s<sup>2</sup> 2p<sup>5</sup>
A)F
B)C
C)N
D)Al
E)O
Answer: A
Q4) 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>
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) 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>
Q2) Identify the compound with the highest pK<sub>a</sub>.
A)CH<sub>3</sub>CH<sub>3</sub>
B)HCCH
C)CH<sub>2</sub>CH<sub>2</sub>
D)CH<sub>3</sub>OH
E)CH<sub>3</sub>NH<sub>2</sub>
Answer: A
Q3) What is the conjugate base of CH<sub>3</sub>NH<sub>2</sub>?
A)CH<sub>3</sub>NH<sub>3</sub><sup>+</sup>
B)CH<sub>3</sub>NH<sup>-</sup>
C)NH<sub>4</sub><sup>+</sup>
D)NH<sub>2</sub><sup>-</sup>
Answer: B
Q4) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
Page 4
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Chapter 3: An Introduction to Organic Compounds:
Nomenclature, physical Properties, and Structure
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Sample Questions
Q1) Draw all ethers with molecular formula C<sub>4</sub>H<sub>10</sub>O.
Answer: 11ea8a1c_2c78_c151_b657_9702040f6a0e_TB1831_00
Q2) Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?
A)chair < boat < twist-boat < half-chair
B)half-chair < boat < twist-boat < chair
C)chair < twist-boat < half-chair < boat
D)chair < twist-boat < boat < half-chair
E)half-chair < twist-boat < boat < chair
Answer: D
Q3) Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane.
Answer: 11ea8a1c_2c7e_66c8_b657_b933e33520d0_TB1831_00 or enantiomer
Q4) Describe the source of angle strain and torsional strain present in cyclopropane. Answer: The angle strain arises from the compression of the ideal tetrahedral bond angle of 109.5° to 60°.The large torsional strain occurs since all C-H bonds on adjacent carbons are eclipsed.
Q5) Give the structure of tetramethylammonium chloride.
Answer: 11ea8a1c_2c79_d2cd_b657_e7855c7ffdba_TB1831_00
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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 (2R,3S)-2,3-dibromohexane.
Q2) (-)-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°
Q3) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.
Q4) Provide a careful structure for (2R,3S,4S)-2-bromo-4-methyl-3-hexanol.
Q5) Which of the following is a true statement?
A)All chiral molecules possess a plane of symmetry.
B)All achiral molecules are meso.
C)All molecules which possess a single chirality center of the S configuration are levorotatory.
D)A mixture of achiral compounds will be optically inactive.
E)All molecules which possess two or more chirality centers will be chiral.
Q6) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
Q7) Draw the stereoisomers of 1,3-dichlorocyclopentane.
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Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) Give the hybridization,shape,and bond angle for a carbon in ethene.
Q2) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.
Q3) 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
Q4) Draw the structure of (Z)-4-ethyl-3-methylheptene.
Q5) Why do reactions tend to proceed at a faster rate as T increases?
Q6) Draw the structure of propyl vinyl ether.
Q7) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
Q8) Identify the nucleophiles and electrophiles.
<sup>-</sup>OH,BH<sub>3</sub>,H<sub>2</sub>O,<sup>+</sup>CH<sub>3</sub>,NH<su b>3</sub>,Br<sup>-</sup>
Q9) Draw (E)-2-methyl-3-hexen-1-ol.
Q10) Draw vinyl bromide.
Page 7
Q11) What is the free energy of activation of a one-step reaction? How is it qualitatively related to the rate constant of the reaction?
Q12) Draw the structure of (Z)-1-chloro-2-methyl-2-butene.
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Chapter 6: The Reactions of Alkenes - the Stereochemistry of
Addition Reactions
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Sample Questions
Q1) Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclopentane as the major organic product.
Q2) 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
Q3) Which statement is true in the hydroboration-oxidation of an alkene?
A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markovnikov orientation and both syn and anti addition occur.
Q4) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
Q5) Give the types of products formed from the bromination and catalytic hydrogenation (using D<sub>2</sub>)of cyclohexene.
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
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Sample Questions
Q1) Give the IUPAC name for (CH<sub>3</sub>)<sub>2</sub>C(CH<sub>2</sub>CH<sub>3</sub>)CCCH(CH<sub>3</ sub>)<sub>2</sub>.
Q2) What two atomic orbitals or hybrid atomic orbitals overlap to form the carbon-carbon bond in ethyne?
A)sp<sup>3</sup>-sp<sup>3</sup>
B)p-p
C)sp<sup>2</sup>-sp<sup>2</sup>
D)s-s
E)sp-sp
Q3) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q4) The pi-bonds in ethyne is formed by
A)end-to-end sp-sp overlap
B)side-to-side sp-sp overlap
C)end-to-end s-sp overlap
D)end-to-end p-p overlap
E)side-to-side p-p overlap
Q6) Provide the structure of (2E,4E)-2-chloro-2,4-octadiene. Page 10
Q5) Draw an acceptable structure for 3-sec-butyl-1-heptyne.
Q7) Give the IUPAC name for HCCCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
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Electronic Effects: an Introduction to the Reactions of
Benzene
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Sample Questions
Q1) Aromatic molecules contain ________ electrons.
A)no
B)4n + 2 (with n an integer)
C)4n + 2 (where n = 0.5)
D)4n (with n an integer)
E)unpaired
Q2) Provide the structure of the biologically significant heterocycle pyrimidine.
Q3) Provide the structure of the biologically significant heterocycle purine.
Q4) Which of the following is the weakest base?
A)phenolate ion (C<sub>6</sub>H<sub>5</sub>O<sup>-</sup>)
B)ethoxide ion (CH<sub>3</sub>CH<sub>2</sub>O<sup>-</sup>)
C)hydroxide ion (HO<sup>-</sup>)
D)acetate ion (CH<sub>3</sub>CO<sub>2</sub><sup>-</sup>)
E)methoxide ion (CH<sub>3</sub>O<sup>-</sup>)
Q6) Is cyclooctatetraene a planar molecule? Explain. Page 12
Q5) Provide a diagram which depicts the relative energies of the molecular orbitals of benzene.Show which molecular orbitals are filled in benzene's ground state.
Q7) Draw (Z)-1,3-hexadiene in its s-trans conformation.
Q8) Draw the s-cis conformation of (2E,4Z)-4-methyl-2,4,-heptadiene.
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Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Sample Questions
Q1) Which of the following halides is least reactive in an E2 reaction with sodium methoxide?
A)(CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>I B)(CH<sub>3</sub>)<sub>2</sub>CHCHICH<sub>3</sub> C)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>Br D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>Cl E)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>Cl
Q2) Give the name(s)of the product(s)of the S<sub>N</sub>1 reaction of 3-bromo-2,2-dimethylbutane with water.
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
Q3) List the following compounds in order of increasing reactivity in an S<sub>N</sub>1 reaction.
CH<sub>3</sub>Br,CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>I,(CH<sub>3</sub> )<sub>3</sub>CI,CH<sub>3</sub>CHBrCH<sub>3</sub>,CH<sub>3</sub>CHICH<sub>3</ sub>
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) Arene oxides are formed
A)by the reaction of cytochrome P<sub>450 </sub>with oxygen.
B)by the reaction of cytochrome P<sub>450</sub> with peroxy acids.
C)by the reaction of cytochrome P<sub>450</sub> with PCC.
D)by the reaction of cytochrome P<sub>450</sub> with alcohols.
E)by the reaction of cytochrome P<sub>450</sub> with aromatic compounds.
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) 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
Q4) 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) 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?
Q2) The following alkyl halide could not be used to form a Grignard reagent.Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q3) Name the three major alkene products that result when 1-pentene is treated with Grubbs catalyst.
Q4) Grignard reagents contain which of the following metals?
A)palladium
B)copper
C)magnesium
D)lithium
E)ruthenium
Q5) In palladium catalyzed coupling reactions,the first step is called A)oxidative elimination.
B)reductive addition.
C)oxidative addition.
D)reductive elimination.
E)none of the above.
Q6) Name the organic products that would result from metathesis of 1,8-nonadiene.
Page 16
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Chapter 12: Radicals
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Sample Questions
Q1) How would you convert 1-butene to 1-hexanol?
Q2) 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
Q3) Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-2-heptene.
Q4) Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-1-heptene.
Q5) What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?
Q6) Provide the structure of semiquinone radical.
Q7) What role do vitamins C and E play in biological radical reactions?
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) Identify the compound with the longest <sub>max</sub> in an UV spectrum.
A)benzene
B)phenol
C)phenolate ion
D)aniline
E)anilinium ion
Q2) Which of the following is not a major peak in the MS of isopentane?
A)29
B)43
C)57
D)60
E)72
Q3) Arrange the following regions of the electromagnetic spectrum in order of decreasing wavelength: microwaves,visible light,ultraviolet light,infrared radiation,X-rays.
Q4) An infrared wavelength of 4.48 m is equivalent to a wavenumber of ________ cm<sup>-1</sup>.
Q5) 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>
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Q6) How can UV spectroscopy be used to estimate the nucleotide composition of DNA?
Chapter 14: Nmr Spectroscopy
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Q1) Deduce the identity of the compound from the data provided. C<sub>8</sub>H<sub>13</sub>Br: IR (cm<sup>-1</sup>): 2950,2150 <sup> 1</sup>H NMR ( ,splitting,integral): 3.5 (t,2H),1.8 (t,2H), 0)9 (s,9H)
<sup> 13</sup>C NMR: 6 signals
A)CH<sub>3</sub>CHBrCCC(CH<sub>3</sub>)<sub>3</sub>
B)HCCCH<sub>2</sub>C(CH<sub>3</sub>)<sub>2</sub>CH<sub>2</sub>CH<sub>2</su b>Br
C)3-bromo-1,2-dimethylcyclohexene
D)4-bromo-1,2,4-trimethylcyclopentene
E)BrCH<sub>2</sub>CH<sub>2</sub>CCC(CH<sub>3</sub>)<sub>3</sub>
Q2) 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>)<sub>3</sub>CCHO.
Q3) An unknown compound,C<sub>4</sub>H<sub>10</sub>O,gave the following proton NMR data:
Triplet at 1.13 ppm
Quartet at 3.38 ppm
What is the structure of the compound?
Q4) Can alkenes and aromatics be easily distinguished from each other in an <sup>13</sup>C NMR spectrum?
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Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Q1) o-Phthalic acid produces what acid derivative upon heating?
A)an ester
B)a carboxylate
C)an acid chloride
D)an anhydride
E)an amide
Q2) What reagents are used to dehydrate amides to nitriles?
Q3) What is the main intramolecular force between two molecules of acetonitrile?
A)London dispersion forces
B)dipole-dipole interaction
C)hydrogen bonding
D)induced dipole interactions
E)none of the above
Q4) What are the products of the reaction of benzoic acid with thionyl chloride?
Q5) Provide a detailed,stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.
Q6) Provide the structure of the tetrahedral intermediate in the reaction of sodium methoxide with propanoyl chloride.
Q7) Provide the proper IUPAC name for ClCH<sub>2</sub>CH<sub>2</sub>CONHCH<sub>3</sub>. Page 20
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Chapter 16: Reactions of Aldehydes and Ketones
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Q1) Which of the following most typically characterizes the reactions of aldehydes and ketones?
A)electrophilic addition
B)electrophilic substitution
C)nucleophilic acyl substitution
D)nucleophilic addition
E)radical addition
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 structure of the compound that results when 4-heptanone is treated with peroxyacetic acid.
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) What reagent can be used to convert benzophenone into triphenylmethanol?
Page 22
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Chapter 17: Reactions at the -Carbon
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Q1) Which of the following compounds will give a positive iodoform test?
A)propanal
B)2-pentanone
C)3-pentanone
D)benzophenone
E)cyclohexanone
Q2) Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.
Q3) Provide a detailed,stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone,hydroxide and iodine.
Q4) List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione,diethyl malonate,propanal,ethyl acetate.
Q5) A -keto ester is a product in which of the following reactions?
A)Aldol condensation
B)Claisen condensation
C)Dieckmann condensation
D)Robinson annulation
E)Michael addition
Q6) How would you convert cyclohexene to 2-methylcyclohexanone?
Page 23
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) What sequence of reagents can be used to make p-butylbenzenesulfonic acid from benzene?
Q2) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.
Q3) Sulfonation can be reversed
A)upon treatment with Zn/HCl.
B)upon treatment with chromic acid.
C)upon treatment with NBS.
D)in dilute acid at 100°C.
E)upon treatment with NaBH<sub>4</sub>.
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.
Q5) In electrophilic aromatic substitution reactions,a chlorine substituent is
A)a deactivator and a m-director
B)a deactivator and an o,p-director
C)an activator and a m-director
D)an activator and an o,p-director
E)none of the above
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) Pyridine does not undergo Friedel-Crafts reactions.Offer an explanation.
Q2) Which heterocyclic ring is present in cytosine DNA base?
A)pyrrole
B)purine
C)pyrimidine
D)porphyrin
E)pyridine
Q3) Draw 4-methylisoquinoline.
Q4) 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.
Q5) What results when cis-2-butene is subjected to the following reaction sequence?
(1)Cl<sub>2</sub>,H<sub>2</sub>O,(2)NaOH,(3)H<sub>3</sub>O<sup>+</sup>?
A)a meso epoxide
B)a 1:1 mixture of enantiomeric epoxides
C)a meso diol
D)a 1:1 mixture of enantiomeric diols
E)2-butanol
Q7) Provide a structural representation of oxetane. Page 25
Q6) Provide the structure of thymine; How is it used by organisms?
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) Which of the following statements best describes the meaning of a glycoside?
A)It is the mirror image of a sugar.
B)It is the hemiacetal of a sugar.
C)It is the acetal of a sugar.
D)It is the enantiomer of a sugar.
E)It is the enol-keto form of a sugar.
Q2) Draw the more stable chair conformer of -D-glucopyranose.
Q3) 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.
Q4) Under what conditions is the methyl glycoside of galactose prepared?
Q5) An aqueous solution of glucose behaves as an aldehyde because
A)it is hydrolyzed by water to the free aldehyde.
B)it is a ketone,but is in equilibrium with the aldehyde form.
C)glucose is actually a cyclic aldehyde.
D)its cyclic hemiacetal,the predominant form,is in equilibrium with the free aldehyde form.
E)it can be oxidized with periodic acid.
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Rate the following amino acids in decreasing order of migration towards the cathode (negative electrode)when separated by electrophoresis in a solution of pH= 7.3.
I.lysine: pI= 9.87
II.alanine: pI= 6.02
III.aspartate: pI= 5.95
Q2) Which of the following is the first step in the determination of the primary structure of proteins?
A)determining the number and kind of amino acids in the peptide
B)reducing the disulfide bridges in the protein
C)protecting the N-terminal of the peptide
D)protecting the C-terminal of the peptide
E)hydrolyzing the protein with dilute acid
Q3) What is the single-letter abbreviation for glutamine?
Q4) Draw the form of L-lysine which is present at biological pH.
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Q1) Which of the following is not true about the enzyme aldolase?
A)It catalyzes the cleavage of D-glucose into two molecules each containing 3-carbons.
B)It catalyzes the cleavage of D-galactose into two molecules each containing 3-carbons.
C)It catalyzes the cleavage of a six carbon compound into two three carbon compounds.
D)It catalyzes the cleavage of D-fructose 1,6-diphosphate into glyceraldehyde-3-phosphate and dihydroxyacetone phosphate.
E)The enzyme is called aldolase because the reverse reaction is an aldol condensation.
Q2) Which of the following statements is not true about catalysts?
A)They can increase the rate of a chemical reaction.
B)They can change the mechanism of a chemical reaction.
C)They are changed in a chemical reaction.
D)They participate in a chemical reaction.
E)They can decrease the activation energy of a chemical reaction.
Q3) Explain what is meant by anchimeric assistance and give an example.
Q4) Provide two ways in which acid catalyzes ester hydrolysis.
Q5) How does a metal 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) In which of the following classes of reactions is a coenzyme required?
A)oxidation reactions
B)two carbon transfer
C)acyl transfer
D)reduction reactions
E)A,B,and D
Q2) What structural feature of enzymes that catalyze redox reactions requires the presence of a coenzyme for reaction to occur?
Q3) Which of the following statements is not true about vitamin K?
A)The letter K comes from koagulation.
B)Vitamin K is required for proper Ca<sup>+2</sup> binding in blood clotting.
C)Kitase is the active coenzyme of vitamin K.
D)Vitamin K is synthesized by intestinal bacteria.
E)Vitamin K is formed in leaves of green plants.
Q4) Identify the true statement(s).You may choose more than one answer.
A)FAD is an oxidizing agent.
B)FADH<sub>2</sub> is an oxidizing agent.
C)FMNH<sub>2</sub> is a reducing agent.
D)NADH is an oxidizing agent.
E)NADPH is a reducing agent.
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Chapter 24: The Organic Chemistry of the Metabolic Pathways
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Q1) 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.
Q2) What organic compound is the most important form of chemical energy?
Q3) Identify the sixth 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>.
Q4) Draw the structure of a fatty acyl-CoA.
Q5) Acetyl-CoA enters the citric acid cycle by reacting with ________ to form
Q7) What class of enzyme puts a phosphoryl group on its substrate? Page 31
Q6) How many molecules of ATP are formed by the citric acid cycle from one molecule of acetyl-CoA?
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Chapter 25: The Organic Chemistry of Lipids
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Q1) Which of the following best explains why the melting points of saturated fats increase with increasing molecular weight?
A)decreased polarity
B)decreased hydrogen bonding
C)increased hydrogen bonding
D)decreased intermolecular van der Waal's interactions
E)increased intermolecular van der Waal's interactions
Q2) How many isoprene units are in a sesquiterpene?
A)1
B)2
C)3
D)4
E)5
Q3) Biosynthesis of terpenes start from A)phosphoglyceride.
B)acetyl CoA.
C)squalene.
D)prostaglandin.
E)cholesterol.
Q4) Provide the structure of -farnesene,a simple,acyclic sesquiterpene.
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Chapter 26: The Chemistry of the Nucleic Acids
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Q1) 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
Q2) Draw the structure of cytidine 5'-phosphate.
Q3) What are stacking interactions in DNA and what purpose do they serve?
Q4) What is a nucleotide? Give an example.
Q5) Show the hydrogen bonding which occurs when adenine and thymine form a base pair.
Q6) What is the most favored reaction when an amino acid and ATP react together?
A)nucleophilic attack on a-phosphorus
B)nucleophilic attack on b-phosphorus
C)nucleophilic attack on g-phosphorus
D)nucleophilic attack on the NH<sub>2</sub> of adenosine
E)nucleophilic attack on the aromatic nitrogen of adenosine
Q7) Name the two pyrimidine bases which serve as components in deoxyribonucleotides.
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Q8) Why is the G°' value for the hydrolysis of ATP large and negative? Give three reasons.
Chapter 27: Synthetic Polymers
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Q1) Give the product for an diisocyanate reacting with a diol.
A)an epoxy resin
B)a polyester
C)a polycarbonate
D)a polyamide
E)a polyurethane
Q2) Identify the monomer(s)that undergo radical polymerization.You may choose more than one answer.
A)styrene
B)methyl methacrylate
C)vinyl chloride
D)methyl vinyl ether
E)acrylamide
Q3) Show the reaction which occurs when benzoyl peroxide is heated.
Q4) Provide the structure of poly(propylene).
Q5) Describe what thermoplastic polymers are.
Q6) In a recycling symbol,the ________ the number in the middle of the symbol,the more easily the compound can be recycled.
Q7) Provide the structure of poly(tetrafluoroethylene).
Q8) What are crystallites?
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Chapter 28: Pericyclic Reactions
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Q1) Is the thermal [4+2] cycloaddition between allylanion and ethylene an allowed one? To answer,draw the HOMO of allyl anion and the LUMO of ethylene,and comment on the symmetry match of the two.
Q2) Which of the following statements concerning electrocyclic reactions is correct?
A)The ground state HOMO of a compound with an even number of conjugated double bonds is asymmetric.
B)The allowed mode of ring closure under thermal conditions for a molecule containing an even number of conjugated double bonds is disrotatory.
C)The allowed mode of ring closure under photochemical conditions for a molecule containing an odd number of conjugated double bonds is disrotatory.
D)both B and C
E)none of the above
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) Under photochemical conditions,is an [2+2] cycloaddition suprafacial or antarafacial?
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