Organic Chemistry II
Textbook Exam Questions
Course Introduction
Organic Chemistry II is an advanced course that builds upon the foundational concepts introduced in Organic Chemistry I, focusing on the structure, properties, and mechanisms of organic molecules. The course delves into more complex reaction mechanisms, including those involving aromatic compounds, carbonyl chemistry, and biomolecules. Topics such as spectroscopy, multi-step synthesis, and the role of organic chemistry in biological systems are examined in detail. Emphasis is placed on problem-solving, laboratory techniques, and critical thinking skills necessary for understanding reaction pathways and designing synthetic strategies relevant to pharmaceuticals, materials, and industrial chemistry.
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) A molecule of acetonitrile CH<sub>3</sub>CN contains ________ sigma bonds and ________ pi bonds.
A)5,2
B)4,3
C)4,2
D)2,2
E)4,0
Answer: A
Q2) Each lone pair of electrons on the O atom in methanol (CH<sub>3</sub>OH)occupies a(n)________ orbital.
A)s
B)p
C)sp
D)sp<sup>2</sup>
E)sp<sup>3</sup>
Answer: E
Q3) How many nonbonding electron pairs,bonding electron pairs,pi bonds,and sigma bonds are present in CO<sub>2</sub>?
Answer: 4 nonbonding electron pairs,4 bonding electrons pairs,2 pi bonds,2 sigma bonds
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) 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
Q2) The amino acid glycine
(H<sub>3</sub>N<sup>+</sup>CH<sub>2</sub>CO<sub>2</sub>H)has two acidic Hs,one with pKa = 2.34 and the other with pKa=9.60.Draw the structure of the form of glycine that predominates at a pH of 12.
Answer: 11ea8a1c_2c72_0a63_b657_ed0d8a56a6c7_TB1831_00
Q3) 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
Page 4
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) Draw the structure of 3-chloro-N-ethyl-2-hexanamine.
Answer: 11ea8a1c_2c79_d2cc_b657_a59a44c828a8_TB1831_00
Q2) Which of the following will have the lowest boiling point?
A)CH<sub>3</sub>Cl
B)CH<sub>4</sub>
C)CH<sub>2</sub>Cl<sub>2</sub>
D)CHCl<sub>3</sub>
E)CCl<sub>4</sub>
Answer: B
Q3) Draw the most stable conformer of trans-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030d_b657_778a7cd7007c_TB1831_00
Q4) Primary and secondary amines exhibit hydrogen bonding; tertiary amines do not.Explain.
Answer: The nitrogen in a tertiary amine is not attached to a hydrogen.Recall that for a molecule to exhibit hydrogen bonding it must have a hydrogen attached to a highly electronegative atom such as F,N,or O.
Q5) Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030c_b657_0556aed4dd3f_TB1831_00
Page 5
Q6) Draw the most stable conformer of cis-1-ethyl-3-methylcyclohexane.
Answer: 11ea8a1c_2c7f_2a1e_b657_673388854856_TB1831_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Q1) The specific rotation of a pure substance is -5.90°.What is the percentage of this isomer in a mixture with an observed specific rotation of -2.95°?
A)25%
B)50%
C)75%
D)80%
E)0%
Q2) How many stereoisomers exist with the following basic connectivity? CH<sub>3</sub>CHClCH<sub>2</sub>CHClCH<sub>3</sub>
A)0
B)1
C)2
D)3
E)4
Q3) 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?
Q4) Provide a careful structure for (2S,3S)-2,3-dibromohexane.
Q5) Provide a careful structure for (2R,3S)-2,3-dibromohexane.
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Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Q1) Which of the following correctly describes intermediates and/or transition states?
A)Transition states occur at minima on reaction coordinate diagrams.
B)Both transition states and intermediates occur at maxima on reaction coordinate diagrams.
C)An intermediate is always produced after the rate-determining step of a reaction mechanism.
D)Transition states have partially formed bonds whereas intermediates have fully formed bonds.
E)none of the above
Q2) Give the hybridization,shape,and bond angle for a carbon in ethene.
Q3) 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
Q4) Draw and name the six alkenes which have the molecular formula C<sub>5</sub>H<sub>10</sub>.
Page 8
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Chapter 6: The Reactions of Alkenes - the Stereochemistry of
Addition Reactions
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Q1) What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
A)2-methylpentane
B)2-methyl-1-pentanol
C)2-methyl-2-pentanol
D)2-methyl-3-pentanol
E)1-methoxypentane
Q2) 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.
Q3) Based on the relative stabilities of the intermediates involved,explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.
Q4) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
Q5) What is hyperconjugation,and how does it affect carbocation stability?
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep
Synthesis
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Q1) 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.
Q2) Why are terminal alkynes more acidic than other hydrocarbons?
Q3) Give the IUPAC name for HCCCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
Q4) Draw an acceptable structure for acetylene.
Q5) The reagent needed to convert 2-butyne to trans-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)C or D.
Q6) Provide the structure of the major organic product that results when 2-butyne is treated with H<sub>2</sub> in the presence of Lindlar's catalyst.
Q7) Draw an acceptable structure for 3-sec-butyl-1-heptyne.
Q8) Provide the structure of (2E,4E)-2-chloro-2,4-octadiene.
Q9) Draw an acceptable structure for 2-hexyne.
Q10) Give the systematic name for the alkyne Page 10
Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
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Chapter
Electronic Effects: an Introduction to the Reactions of
Benzene
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Q1) 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.
Q2) In the molecular orbital representation of benzene,how many molecular orbitals are present?
A)1
B)2
C)4
D)6
E)8
Q3) Which of the following statements about the molecular orbital description of cyclobutadiene is not correct?
A)Cyclobutadiene has two degenerate nonbonding molecular orbitals.
B)Cyclobutadiene has a single bonding molecular orbital.
C)Cyclobutadiene has two electrons in nonbonding molecular orbitals.
D)Cyclobutadiene has one electron in an antibonding molecular orbital which makes it antiaromatic.
E)none of the above
Q4) Which MOs are bonding MOs in the ground state of 1,3,5-hexatriene? Page 12
Q5) Provide the structure of the biologically significant heterocycle purine.
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Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Sample Questions
Q1) Which of the following bromides reacts readily via an S<sub>N</sub>2 reaction with NaN<sub>3</sub>?
A)C<sub>6</sub>H<sub>5</sub>Br
B)CH<sub>3</sub>CH<sub>2</sub>CH=CHBr
C)(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CBr
D)(CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br E)1-bromo-1-methylcyclohexane
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 species is most reactive in an S<sub>N</sub>2 reaction?
A)CH<sub>3</sub>CH<sub>2</sub>-Cl
B)CH<sub>3</sub>CH<sub>2</sub>-Br
C)CH<sub>3</sub>CH<sub>2</sub>-I
D)CH<sub>3</sub>CH<sub>2</sub>-F
E)CH<sub>3</sub>CH<sub>2</sub>-OH
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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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) A compound (A)C<sub>4</sub>H<sub>10</sub>O is optically active.(A)reacts with HCl and ZnCl<sub>2</sub> (Lucas test)to form a cloudy product within 10 minutes.Deduce the structure of (A).
Q3) 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.
Q4) Why are alcohols typically poor electrophiles?
Q5) Draw the tosylate ion and explain why it is a particularly good leaving group.
Q6) How are certain arene oxides believed to cause cancer?
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Chapter 11: Organometallic Compounds
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Q1) 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
Q2) Name the organic products that would result from metathesis of 1,8-nonadiene.
Q3) 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
Q4) Name the three major alkene products that result when 1-pentene is treated with Grubbs catalyst.
Q5) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q6) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
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Chapter 12: Radicals
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Q1) In the free radical chlorination of ethane,the step in which the Cl radical abstracts a H atom from ethane is ________ and the transition state most closely resembles
A)exothermic,the reactants
B)endothermic,the reactants
C)exothermic,the products
D)endothermic,the products
E)endothermic,a carbocation
Q2) Write an equation to describe the initiation step in the chlorination of methane.
Q3) NBS is frequently used in the bromination of allylic carbons to provide
A)high concentration of bromine needed for the reaction.
B)low concentration of bromine needed for the reaction.
C)high concentration of HBr needed for the reaction.
D)low concentration of HBr needed for the reaction.
E)B and D
Q4) Devise methods by which (CH<sub>3</sub>)<sub>2</sub>CCH<sub>2</sub> could be synthesized from 2-methylpropane.
Q5) Explain how CFCs are linked to depletion of stratospheric ozone.
Q6) Why are alkanes so unreactive?
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Q1) In electron ionization,a sample is bombarded with a beam of high energy A)protons.
B)neutrons.
C)electrons. D)positrons.
E)ions.
Q2) The mass spectra of alcohols often fail to exhibit detectable M peaks but instead show relatively large ________ peaks.
A)M+1
B)M+2
C)M-16
D)M-17
E)M-18
Q3) Describe the molecular ion region in the mass spectrum of CH<sub>3</sub>CH<sub>2</sub>Br.
Q4) 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>
Q5) Which region of the electromagnetic spectrum,radio or visible,is characterized by waves of shorter wavelength?
Q6) Give the m/z ratio of the molecular ion in the mass spectrum of 1-butanol. Page 18
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Chapter 14: Nmr Spectroscopy
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Sample Questions
Q1) Deduce the identity of the following compound from the <sup>1</sup>H NMR spectral data given.
C<sub>6</sub>H<sub>8</sub>O<sub>4</sub> : 3.9 (6H,singlet),6.1 (2H,singlet)(ppm)
Q2) 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>
Q3) Provide the structure that is consistent with the data below.
C<sub>5</sub>H<sub>8</sub>Cl<sub>2</sub>
IR (cm<sup>-1</sup>): 2950
<sup>1</sup>H NMR (d): 1.4 (4H,t),1.2 (4H,t)
<sup>13</sup>C NMR (d): 62 (s),26 (t),23 (t)
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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Q1) What is the main intramolecular force between two molecules of N,N-dimethylacetamide?
A)London dispersion forces
B)dipole-dipole interaction
C)hydrogen bonding
D)induced dipole interactions
E)none of the above
Q2) Provide a detailed,stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.
Q3) Provide a detailed,stepwise mechanism for the reaction of butyrolactone with ammonia.
Q4) Provide a detailed,stepwise mechanism for the reaction of propanoyl chloride with ammonia.
Q5) The hydrolysis of esters in base is called
A)the Fischer esterification.
B)the Hunsdiecker reaction.
C)the Dieckmann condensation.
D)transesterification.
E)saponification.
Page 21
Q6) Provide the structure of propanoic anhydride.
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Chapter 16: Reactions of Aldehydes and Ketones
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Q1) Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.
Q2) Provide the major organic product of the reaction of aniline with 3-pentanone.
Q3) Draw the structure of 3,3-dimethyl-4-oxopentanal.
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) Draw the structure of 3-bromobutanal.
Q6) Provide the structure of the acetal that results when 4-heptanone is dissolved in methanol containing an acid catalyst.
Q7) Which of the following amines will react with cyclopentanone to form an enamine?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
B)(CH<sub>3</sub>)<sub>3</sub>N
C)pyridine
D)(CH<sub>3</sub>)<sub>3</sub>CNH<sub>2</sub>
E)none of the above
Q8) Provide the structure of the hydrate of cyclopentanone.
Q10) Provide the structure of the diethyl acetal of butanal. Page 23
Q9) Provide the structure of the cyanohydrin that results when cyclopentanone reacts with HCN.
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Chapter 17: Reactions at the -Carbon
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Q1) What product is formed in the mixed Claisen condensation between methyl benzoate and cyclohexanone?
Q2) Provide a detailed,stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.
Q3) An enolate attacks an aldehyde and the resulting product is subsequently protonated.What type of reaction is this?
A)a Fischer esterification
B)an acid-catalyzed aldol condensation
C)a base-mediated aldol condensation
D)a Hell-Volhard-Zelinsky reaction
E)a Selman-Jones reaction
Q4) Rank the following compounds in order of increasing acidity of their a-Hs,least acidic to most acidic: CH<sub>3</sub>CH<sub>2</sub>CON(CH<sub>3</sub>)<sub>2</sub>,PhCOCH<sub>2</ sub>CHO,CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3< /sub>,and PhCOCH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
Q5) How would you convert cyclohexene to 2-methylcyclohexanone?
Q6) Why is the pKa of acetone 20 while that of ethane is 50? Explain the origin for this difference in acidity.
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) Provide the structure of dibenzyl ether.
Q2) Which of the following substituent on the benzene ring is a meta director?
A)-Cl
B)-COOH
C)-CHO
D)B and C
E)all of the above
Q3) In electrophilic aromatic substitution,a halogen substituent is considered as
A)strongly activating.
B)strongly deactivating.
C)weakly activating.
D)weakly deactivating.
E)moderately activating.
Q4) Can one distinguish among the three isomeric xylenes using <sup>13</sup>C NMR? Explain.
Q5) Draw the four major resonance structures of the carbocation intermediate in the reaction of anisole with HNO<sub>3</sub>/H<sub>2</sub>SO<sub>4</sub> to yield p-nitroanisole.
Page 26
Q6) In the bromination of benzene using Br<sub>2</sub> and FeBr<sub>3</sub>,is the intermediate carbocation aromatic? Explain.
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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) 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.
Q3) Show how the dipole moments are oriented in pyrrolidine and pyrrole,and explain why they are oriented in opposite directions.
Q4) Pyridine does not undergo Friedel-Crafts reactions.Offer an explanation.
Q5) 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
Q6) Provide the structure of thymine; How is it used by organisms?
Q7) Draw the structure of piperidine.
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Q8) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) Which of the following blood types is known as the universal acceptor?
A)A
B)B
C)AB
D)O
E)ABO
Q2) Fructose is described as a(n) A)aldopentose. B)ketopentose. C)aldohexose. D)ketohexose. E)none of the above.
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) Which of the D-aldopentoses yields an optically inactive aldonic acid upon oxidation with bromine water? Explain your answer.
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Which type of protein,globular or fibrous,tends to function primarily as structural parts of an organism?
Q2) Draw the predominant form of histidine at pH=0.
Q3) Three dimensional structure of the peptides is also called a
A)primary structure.
B)secondary structure.
C)tertiary structure.
D)ternary structure.
E)quaternary structure.
Q4) Describe how electrophoresis works.
Q5) Phenyl isothiocyanate (PITC)is commonly known as Edman's reagent.Edman's reagent is widely used to identify which of the following?
A)the number and kind of amino acids in the protein
B)the disulfide bridges in the protein
C)C-terminal amino acid of the protein
D)N-terminal amino acid of the protein
E)the number of peptide bonds in the protein
Q6) Draw the dipeptide Val-Tyr at pH 7.0.
Q7) How is the enzyme chymotrypsin used in peptide structure determination?
Q8) What is an amino acid analyzer?
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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) Provide two ways in which acid catalyzes ester hydrolysis.
Q3) What are NAM and NAG and what do they do?
Q4) The end product of glycolysis is
A)D-glucose.
B)aldolase.
C)fructose-1,6-bisphosphate.
D)glyceraldehyle-3-phosphate.
E)pyruvate.
Q5) How does an acid catalyst increase the rate of reaction?
Q6) Why is histidine a versatile catalytic group?
Q7) Explain what is meant by anchimeric assistance and give an example.
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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 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.
Q2) Identify all group(s)that tetrahydrofolate transfers.
A)methylene
B)methyl
C)ethyl
D)formyl
E)A,B,and D
Q3) Which of the following statements is true about metabolism?
A)reactions that living organisms carry out to obtain energy and to synthesize required compounds
B)reactions that organic chemists carry out to obtain energy and to synthesize required compounds
C)reactions that consist of catabolic and anabolic reactions
D)A and C
E)B and C
Page 32
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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) At biological pH,ATP has ________ negative charges per molecule.
A)4)0
B)3)3
C)2)8
D)1)1
E)0)6
Q3) A phosphoanhydride bond is known as a ________ bond.
A)low-energy
B)high-energy
C)hydrogen
D)disulfide
E)pericyclic
Q4) 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.
Q5) Draw the structure of pyruvate.
Q7) a-Ketoglutarate is an intermediate in the citric acid cycle.Draw its structure. Page 33
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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Q1) Identify the compound that would be formed from the hydrogenation of linolenic acid.
A)palmitic acid
B)lauric acid
C)stearic acid
D)myristic acid
E)linoleic acid
Q2) 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
Q3) Squalene is a
A)monoterpene.
B)sesquiterpene.
C)diterpene.
D)triterpene.
E)carotenoid.
Q4) Provide the structure of -farnesene,a simple,acyclic sesquiterpene.
Page 35
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Chapter 26: The Chemistry of the Nucleic Acids
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Q1) All tRNAs have ________ at the 3'-end.
A)CCA
B)UUC
C)GCC
D)CAG
E)GGA
Q2) What are the four common ribonucleosides?
Q3) Give the first step of PCR.
A)esterification
B)strand separation
C)base-pairing of the primers
D)DNA synthesis
E)hydrolysis
Q4) What is a nucleoside? Give an example.
Q5) Which of the following are known as pyrimidines?
A)cytosine and thymine
B)adenine and cytosine
C)adenine and thymine
D)guanine and thymine
E)adenine and guanine
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Chapter 27: Synthetic Polymers
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Q1) The joining together of many monomers to form a very large molecule is called
A)polymerization.
B)monomerization.
C)dimerization.
D)hydroxylation.
E)homogenization.
Q2) Describe what thermoplastic polymers are.
Q3) 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
Q4) ABS is a copolymer of what three monomers?
Q5) What is the main structural difference between high-density and low-density polyethylene,and how does this structural difference affect the properties and uses of these polymers?
Q6) In a recycling symbol,the ________ the number in the middle of the symbol,the more easily the compound can be recycled.
Q7) Show the reaction which occurs when benzoyl peroxide is heated.
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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) Which of the following statements best describes what is meant by pericyclic reactions?
A)reactions in which a nucleophile reacts with an electrophile B)reactions in which an electrophile reacts with a nucleophile C)reactions in which a free radical reacts with another free radical D)oxidation-reduction reactions in which electrons are lost or gained E)reactions that occur as a result of a cyclic reorganization of electrons
Q3) (a)Under thermal conditions,will ring closure of (2E,4Z,6Z,8E)-decatetraene be conrotatory or disrotatory? Explain.
(b)Will the product be cis or trans? Explain
Q4) What pericyclic photochemical reaction can lead to skin cancer in humans? Draw the structure of the compounds involved in the reaction,and explain how this reaction leads to skin cancer.
Page 38
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