Organic Chemistry II
Pre-Test Questions
Course Introduction
Organic Chemistry II builds upon the foundational concepts introduced in Organic Chemistry I, delving deeper into the structure, properties, and reactivity of organic molecules. This course covers advanced topics such as aromaticity, electrophilic and nucleophilic aromatic substitution, carbonyl chemistry, carboxylic acids and their derivatives, enol and enolate chemistry, and amines. Students will also explore mechanisms and synthesis strategies, gaining practical skills in interpreting spectroscopic data and solving complex synthetic problems. Emphasis is placed on reaction mechanisms, multi-step syntheses, and the application of organic chemistry principles to biological and industrial contexts.
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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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) 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
Q3) Which of the following contain(s)polar covalent bonds?
A)NH<sub>3</sub>
B)Na<sub>2</sub>O
C)H<sub>2</sub>
D)KF
E)both A and C
Answer: A
Q4) What orbitals overlap to create the C-H bond in ethene (H<sub>2</sub>C=CH<sub>2</sub>)?
A)s-sp
B)s-sp<sup>2</sup>
C)s-sp<sup>3</sup>
D)s-p
E)p-p
Answer: B
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) What is the pH of a 0.1 M solution of HCl? (Note: pK<sub>a</sub> for HCl is -6.)
A)6
B)-6
C)1
D)-8
E)-1
Answer: C
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) 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
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) Which of the following statements about the conformers that result from rotation about the C2-C3 bond of butane is correct?
A)The highest energy conformer is one in which methyl groups are eclipsed by hydrogens.
B)The gauche conformer is an eclipsed one.
C)Steric strain is absent in the eclipsed forms.
D)Torsional strain is absent in the eclipsed forms.
E)none of the above
Answer: E
Q2) 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
Q3) Draw an acceptable structure for 4-isopropyl-2-methylheptane.
Answer: 11ea8a1c_2c75_db0b_b657_11055e9043ed_TB1831_00
Q4) Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030c_b657_0556aed4dd3f_TB1831_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Q1) Which of the following is not true of enantiomers?
A)They have the same melting point.
B)They have the same boiling point.
C)They have the same chemical reactivity with non-chiral reagents.
D)They have the same density.
E)They have the same specific rotation.
Q2) How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?
A)0
B)1
C)2
D)3
E)4
Q3) Provide a careful structure for (2R,3S,4S)-2-bromo-4-methyl-3-hexanol.
Q4) Provide a perspective drawing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.
Q5) A solution containing 0.96 g of 2-bromooctane in 10 mL ether solution gave an observed rotation of -1.8° in a 10 cm cell at 20°C.Calculate the specific rotation of this solution.
Q6) Draw a perspective formula of (2R,3S)-3-bromo-2-butanol.
Q7) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
Page 6
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Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) Given an activation energy of 15 kcal/mol,use the Arrhenius equation to estimate how much faster the reaction will occur if the temperature is increased from 100°C to 120°C.R = 1.987 cal/mol K.
Q2) 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
Q3) Draw and name the six alkenes which have the molecular formula C<sub>5</sub>H<sub>10</sub>.
Q4) Draw the structure of (Z)-4-ethyl-3-methylheptene.
Q5) Draw the structure of propyl vinyl ether.
Q6) Draw (E)-2-methyl-3-hexen-1-ol.
Q7) 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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Q1) What is hyperconjugation,and how does it affect carbocation stability?
Q2) 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.
Q3) Give the types of products formed from the bromination and catalytic hydrogenation (using D<sub>2</sub>)of cyclohexene.
Q4) Give the intermediate for the halohydrin reaction.
A)a halonium ion
B)the most stable carbocation with OH on the adjacent carbon
C)the most stable carbocation with X on the adjacent carbon
D)a cyclic oxonium ion
E)the most stable carbanion
Q5) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
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Q6) Based on the relative stabilities of the intermediates involved,explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.
Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
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Q1) A mixture of 1-heptyne,2-heptyne,and 3-heptyne was hydrogenated in the presence of a platinum catalyst until hydrogen uptake ceased.If one assumes that the hydrogenation went to completion,how many distinct seven-carbon hydrocarbons were produced?
A)1
B)2
C)3
D)6
E)8
Q2) Give the IUPAC name for BrCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>2</sub>CH<sub>3</sub>.
Q3) ________ is produced when 1 equivalent of HBr is added to 1-hexyne.
A)2-bromo-1-hexene
B)E-1-bromo-1-hexene
C)Z-1-bromo-1-hexene
D)A mixture of E and Z isomers of 1-bromo-1-hexene
E)E-2-bromo-2-hexene
Q4) Draw an acceptable structure for 2-hexyne.
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Q5) Provide the structure of the major organic product that results when 2-butyne is treated with 1 equivalent of Br<sub>2</sub>.
Chapter
Electronic Effects: an Introduction to the Reactions of
Benzene
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Q1) Consider the hydrogenation reaction of each compound listed and rank the compounds in order of increasing H° of this reaction.The most negative H° should be listed first.
cis-2-pentene,2,3-pentadiene,and trans-1,3-pentadiene
Q2) In which of the following does resonance delocalization of electron density not play a role?
A)allyl cation
B)benzyl anion
C)CO<sub>3</sub><sup>2-</sup>
D)O<sub>3</sub>
E)cyclohexyl radical
Q3) Among a series of isomeric trienes,the more negative the H° of the hydrogenation reaction of a given triene,the ________ stable it is relative to the others in the isomeric series.
Q4) Show how the p orbitals overlap to form the nonbonding molecular orbital of the allyl system.
Q5) Rank the following dienes in order of increasing stability: Page 10
trans-1,3-pentadiene,cis-1,3-pentadiene,1,4-pentadiene,and 1,2-pentadiene.
Q6) Draw the s-trans 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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Q1) What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?
A)(E)-2-phenyl-2-butene
B)(Z)-2-phenyl-2-butene
C)(S)-3-phenyl-1-butene
D)(R)-3-phenyl-1-butene
E)(R)-2-methoxy-2-phenylbutane
Q2) Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.
Q3) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
Q4) Give the product from the reaction of 1-pentene with the following reagents.
1.Cl<sub>2</sub>
2.<sup>-</sup>OH
3.NaNH<sub>2</sub>
4.CH<sub>3</sub>CH<sub>2</sub>Br
Q5) Which of the following alkyl chlorides would undergo substitution most rapidly when treated with NaCCH: chloroethane,2-chloropropane,or 1-chloro-2,2-dimethylpropane?
Provide the structure of the substitution product.
Q6) 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) Why are alcohols typically poor electrophiles?
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) 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>
Q5) How are certain arene oxides believed to cause cancer?
Page 13
Q6) Provide the structure of the major organic product which results when naphthalene oxide undergoes rearrangement in the presence of water.Explain the regioselectivity of this rearrangement.
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Chapter 11: Organometallic Compounds
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Q1) The following alkyl halide could not be used to form a Grignard reagent.Explain.
HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q2) 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?
Q3) 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.
Q4) Which of the following is the strongest base?
A)HOMgBr
B)H<sub>2</sub>O
C)CH<sub>4</sub>
D)CH<sub>3</sub>OH
E)CH<sub>3</sub>MgBr
Q5) 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
Page 15
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Chapter 12: Radicals
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Q1) The reaction Br<sub>2</sub> + CH<sub>3</sub>Br CH<sub>2</sub>Br<sub>2</sub> + HBr was carried out.Which of the following mechanism steps is productive,but relatively unlikely to occur?
A)Br + CH<sub>3</sub>Br HBr + CH<sub>2</sub>Br
B)Br + CH<sub>2</sub>Br CH<sub>2</sub>Br<sub>2</sub>
C)Br + Br<sub>2</sub> Br<sub>2</sub> + Br
D)Br + CH<sub>3</sub> CH<sub>3</sub>Br
Q2) Provide the structure of semiquinone radical.
Q3) How many electrons are contained in the p orbital of the methyl radical?
A)zero
B)one
C)two
D)three
Q4) How many distinct alkyl chlorides can be obtained from monochlorination of 2,3-dimethylpentane?
A)5
B)8
C)10
D)12
E)16
Page 16
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Q1) What does "m/z" stand for and what does it mean?
Q2) In IR spectroscopy,the intensity of a peak is dependent on A)the strength of the bond.
B)the mass of atoms.
C)the polarity of the bond.
D)temperature of the room.
E)none of the above.
Q3) Describe the molecular ion region in the mass spectrum of CH<sub>3</sub>CH<sub>2</sub>Br.
Q4) Which of the following species has a characteristic absorption at 1250 cm<sup>-1</sup> in its IR spectrum?
A)PhCH<sub>2</sub>CN
B)PhCH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>
C)PhCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>
D)PhCH<sub>2</sub>CH<sub>2</sub>OH
E)PhCH<sub>2</sub>OCH<sub>3</sub>
Q5) Which region of the electromagnetic spectrum,IR or UV,contains photons of the higher energy?
Page 17
Q6) Which region of the electromagnetic spectrum,radio or visible,is characterized by waves of shorter wavelength?
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Chapter 14: Nmr Spectroscopy
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Q1) What information does a HETCOR spectrum give?
Q2) The chair form of cyclohexane has protons in two distinct environments,axial and equatorial.When the proton NMR of cyclohexane is run on a 100 MHz instrument at 23°C,only one signal for the compound is observed.Explain this apparent contradiction.
Q3) What is indicated by a cross peak in the COSY spectrum of a compound?
Q4) Deduce the identity of the following compound from the spectral data given. C<sub>7</sub>H<sub>10</sub>O<sub>2</sub>: <sup>1</sup>H NMR, 1.16 (3H,singlet),2.21 (2H,singlet); <sup>13</sup>C NMR, 216.25 (singlet),52.57 (singlet),34.51 (triplet),20.22 (quartet)
Q5) Give one reason why <sup>13</sup>C NMR is less sensitive than <sup>1</sup>H NMR.
Q6) An unknown compound,C<sub>4</sub>H<sub>8</sub>Br<sub>2</sub>,gave the following proton NMR data: Singlet at 1.97 ppm (6H) Singlet at 3.89 ppm (2H) What is the compound?
Q7) Deduce the identity of the compound from the data provided. C<sub>5</sub>H<sub>10</sub>O<sub>2</sub>: IR (cm<sup>-1</sup>): 2950,1740; <sup>13</sup>C NMR ( ,splitting): 15.8 (q),19.7 (q),68.4 (d),195.3 (s)
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Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Q1) Which of the following esters undergoes hydrolysis in base most easily?
A)CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> B)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> C)C<sub>6</sub>H<sub>5</sub>O<sub>2</sub>CCH<sub>3</sub> D)p-CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>CCH<sub>3</sub> E)p-NO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>CCH<sub>3</sub>
Q2) What are the products of the reaction of benzoic acid with thionyl chloride?
Q3) Provide a detailed,stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.
Q4) When benzoyl chloride is reacted with ammonia to prepare benzamide,two equivalents of ammonia must be used.Explain why this is the case.
Q5) Provide the structure of propanoic anhydride.
Q6) What is the hybridization and geometry of the carbonyl carbon in carboxylic acids and their derivatives?
A)sp<sup>3</sup>,tetrahedral B)sp<sup>2</sup>,trigonal planar C)sp<sup>2</sup>,tetrahedral D)sp<sup>3</sup>,trigonal planar E)sp,trigonal planar
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Chapter 16: Reactions of Aldehydes and Ketones
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Q1) By which single-step process can benzene be readily converted into acetophenone?
Q2) Provide the structure of the cyanohydrin that results when cyclopentanone reacts with HCN.
Q3) 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
Q4) Identify the compound whose molecular formula and proton NMR spectra are given below:
C<sub>15</sub>H<sub>14</sub>O; a)triplet,at 2.1 ppm (2H)
b)triplet,at 2.4 ppm (2H)
c)multiplet,at 7.9 - 7.2 ppm (10H)
Q5) Provide the structure of the imine that results when 4-heptanone is treated with CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> in the presence of an acid catalyst.
Q6) Draw the structure of 3-bromobutanal.
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Q7) Provide the major organic product of the reaction of aniline with 3-pentanone.
Chapter 17: Reactions at the -Carbon
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Q1) 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>.
Q2) Provide the structure of the major organic product that results when 4-methylhexanal is heated in base and undergoes and aldol addition followed by a dehydration.
Q3) When the 1,7-diester CH<sub>3</sub>O<sub>2</sub>CCH<sub>2</sub>CH<sub>2</sub>CH(CH<sub>3</sub>) CH<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?
A)an acyclic -diketone
B)an acyclic -ketoacid
C)an acyclic -diester
D)a cyclic -ketoester
E)a cyclic -diketone
Q4) List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione,diethyl malonate,propanal,ethyl acetate.
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) Draw benzyl bromide.
Q2) Why must Friedel-Crafts acylation reactions be run with more than a single equivalent of AlCl<sub>3</sub>?
Q3) How many signals does one expect in the proton decoupled <sup>13</sup>C NMR spectrum of o-xylene?
A)8
B)6
C)4
D)3
E)2
Q4) What reagent is used to convert an arenediazonium salt into a fluoroarene?
A)HBF<sub>4</sub>
B)F<sub>2</sub>
C)HF
D)BF<sub>3</sub>
E)B<sub>2</sub>F<sub>6</sub>
Q5) Provide the structure of benzoic acid.
Q6) Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.
Q7) Draw p-aminobenzoic acid.
Page 23
Q8) What sequence of reagents can be used to make m-butylbenzoic acid from
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) 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
Q2) What is the stereochemistry of the product in the acid hydrolysis of trans-2,3-epoxybutane?
Q3) Provide the structure of thymine; How is it used by organisms?
Q4) Draw the structures of the keto forms of both 2-hydroxypyridine and 4-hydroxypyridine.
Q5) Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.
Q6) Draw the structures of piperidine and morpholine and explain their relative basicities.
Q7) Show how the dipole moments are oriented in pyrrolidine and pyrrole,and explain why they are oriented in opposite directions.
Q9) Provide a structural representation of oxetane. Page 25
Q8) Pyridine does not undergo Friedel-Crafts reactions.Offer an explanation.
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) 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?
A)0
B)1
C)4
D)5
E)6
Q2) Which of the following sequences is known as a Kiliani-Fischer chain elongation?
A)1)Fe<sup>3+</sup>,H<sub>2</sub>O<sub>2</sub> 2.Br<sub>2</sub>,H<sub>2</sub>O 3.Ca(OH)<sub>2</sub>
B)1)CN<sup>-</sup> 2.H<sub>2</sub>,Pd/BaSO<sub>4</sub>
3.H<sub>3</sub>O<sup>+</sup>
C)1)NaBH<sub>4</sub> 2.H<sub>2</sub>O 3.Br<sub>2</sub>,H<sub>2</sub>O
D)1)acetic anhydride (excess),pyridine 2.CH<sub>3</sub>I (excess),Ag<sub>2</sub>O
E)1)CH<sub>3</sub>OH,H<sup>+</sup>, 2.AgNO<sub>3</sub>,
Q3) Draw the most stable chair conformer of D-glucose.
Q4) Draw L-erythrose.
Q5) Why is -D-glucopyranose more stable in nature than -D-glucopyranose?
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Peptidases cause the
A)hydrolysis of peptide bonds.
B)formation of peptide bonds.
C)hydrolysis of disulfide bonds.
D)formation of disulfide bonds.
E)all of the above.
Q2) Which of the following amino acids is not an aromatic compound?
A)phenylalanine
B)threonine
C)histidine
D)tryptophan
E)tyrosine
Q3) 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
Q4) Draw and name the amino acids which may be described as heterocyclic.
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Q1) Which of the following is the best definition of a catalyst?
A)It increases the rate of a chemical reaction.
B)It decreases the rate of a reaction.
C)It decreases activation energy.
D)It increases activation energy.
E)A and C
Q2) How does a metal catalyst increase the rate of reaction?
Q3) Metal ions are
A)Lewis acids.
B)Lewis bases.
C)Bronsted acids.
D)Bronsted bases.
E)none of the above.
Q4) How does an acid catalyst increase the rate of reaction?
Q5) Hydrolysis of esters occurs more rapidly in the presence of catalytic imidazole.Explain this phenomenon and provide the structure of the acyl imidazole intermediate which is formed in the catalyzed process.
Page 29
Q6) How does a base catalyst increase the rate of reaction?
Q7) List four common types of catalysts used in organic reactions and give one example of each.
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Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
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Q1) What are catabolic and anabolic reactions?
Q2) What metal ion is also required by biotin-dependent enzymes?
Q3) Show the transimination (trans-Schiffization)reaction that happens in all PLP-requiring enzymes in which the amino acid substrate forms a Schiff base with PLP,thereby freeing the lysine side chain.
Q4) All redox chemistry of the pyridine nucleotide coenzymes takes place at the ________-position of the pyridine ring.
Q5) Give the purpose of coenzyme B<sub>12 </sub>in rearrangement reactions.
Q6) Which of the following is/are coenzyme(s)formed from the vitamin niacin?
A)NAD<sup>+</sup>
B)NADP<sup>+</sup>
C)NADH
D)NADPH
E)all of the above
Q7) 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 Page 31
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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) Identify the steps that occur in catabolism.
A)Fats,carbohydrates,and proteins are hydrolyzed.
B)digestion
C)NADH is converted to ATP.
D)citric acid cycle
E)All steps occur.
Q3) Of the following compounds,which are consumed 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) What coenzyme is required to facilitate the conversion of glycerol-3-phosphate into dihydroxyacetone?
Q6) What explains the kinetic stability of ATP in aqueous media at biological pH? Page 33
Q5) a-Ketoglutarate is an intermediate in the citric acid cycle.Draw its structure.
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Chapter 25: The Organic Chemistry of Lipids
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Q1) 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.
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) Which of the following fatty acids cannot be synthesized by mammals but must be included in the diet because it is needed to synthesize arachidonic acid which in turn will synthesize prostaglandins?
A)lauric acid
B)palmitic acid
C)arachidic acid
D)linoleic acid
E)oleic acid
Q4) Provide the structure of -farnesene,a simple,acyclic sesquiterpene.
Q5) Why do most naturally occurring fatty acids contain an even number of carbon atoms?
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Chapter 26: The Chemistry of the Nucleic Acids
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Sample Questions
Q1) Draw the structure of ATP.
Q2) What are Maxam-Gilbert and Sanger sequencing?
Q3) Draw the structure of UDP.
Q4) What is genetic engineering?
Q5) What is a nucleoside? Give an example.
Q6) All tRNAs have ________ at the 3'-end.
A)CCA
B)UUC
C)GCC
D)CAG
E)GGA
Q7) The human genome contains approximately how many base pairs?
A)300
B)300,000
C)3 × 10<sup>9</sup>
D)3 × 10<sup>15</sup>
E)3 × 10<sup>23</sup>
Q8) Draw the deaminated product of adenine.
Q9) Name the two pyrimidine bases which serve as components in deoxyribonucleotides. Page 36
Q10) What are antigene and antisense agents?
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Chapter 27: Synthetic Polymers
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Q1) Provide the structure of poly(vinyl chloride).
Q2) Kevlar is an example of
A)a polyester.
B)an aramide.
C)a polyurethane.
D)a epoxy resin.
E)a plasticizer.
Q3) Identify the initiator in a radical polymerization.
A)KOH
B)BuLi
C)CH<sub>3</sub>OOCH<sub>3</sub>
D)BF<sub>3</sub>,H<sub>2</sub>O
E)HCl
Q4) Name the monomer used in the production of neoprene.
Q5) What are aramides?
A)aromatic polyester polymers
B)aromatic amine polymers
C)alkyl halide polymers
D)aromatic polyamide polymers
E)aliphatic polyamide polymers
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Chapter 28: Pericyclic Reactions
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Q1) Under photochemical conditions,is an [2+2] cycloaddition suprafacial or antarafacial?
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) Which of the following molecular orbitals are formed from subtractive overlap of atomic orbitals?
A)antibonding orbitals
B)out-of-phase orbitals
C)bonding orbitals
D)A and B
E)B and C
Q4) 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.
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