Course Introduction
General Chemistry II Exam Questions
General Chemistry II is a continuation of foundational chemistry principles, building upon topics introduced in General Chemistry I. This course explores concepts such as chemical kinetics, chemical equilibrium, acids and bases, thermodynamics, electrochemistry, and introductory nuclear and organic chemistry. Through a combination of theoretical instruction and laboratory work, students gain a deeper understanding of the behavior of matter and energy on a molecular level. Emphasis is placed on the application of chemical principles to both real-world contexts and advanced scientific fields, preparing students for further study in chemistry and related disciplines.
Recommended Textbook
Organic Chemistry 7th 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) Determine the number of pi bonds in CH<sub>3</sub>CN.
A)0
B)1
C)2
D)3
E)4
Answer: C
Q2) 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
Q3) Identify the hybridization of carbon in H<sub>2</sub>CO.
A)sp
B)sp<sup>2</sup>
C)sp<sup>3</sup>
D)sp<sup>4</sup>
E)s<sup>3</sup>p
Answer: B
Q4) Draw the Lewis structure for CH<sub>3</sub>N<sub>2</sub><sup>+</sup>.
Answer: 11ea7d6e_065b_de7b_8568_eb16ffb246da_TB1830_00_TB1830_00
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) Consider the set of compounds, NH<sub>3</sub>, HF, and H<sub>2</sub>O. Rank these compounds in order of increasing acidity and discuss your rationale.
Answer: NH<sub>3</sub> < H<sub>2</sub>O < HF
When determining relative acidity, it is often useful to look at the relative basicity of the conjugate bases. The stronger the acid, the weaker (more stable, less reactive)the conjugate base. In this case, one would look at the relative basicity of F<sup>-</sup>, OH<sup>-</sup>, and NH<sub>2</sub><sup>-</sup>. The relative strengths of these species can be gauged based on the electronegativity of the charged atom in each base. Since fluorine is the most electronegative, F<sup>-</sup> is the most stable, least reactive base in the group. This means that its conjugate acid, HF, is the strongest.
Q2) Which of the following is the strongest acid?
A)CH<sub>3</sub>OH
B)CH<sub>3</sub>OH<sub>2</sub><sup>+</sup>
C)H<sub>2</sub>N<sup>-</sup>
D)CH<sub>3</sub>NH<sub>2</sub>
E)CH<sub>3</sub>NH<sub>3</sub><sup>+</sup>
Answer: B
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Page 4
Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) In the boat conformation of cyclohexane, the "flagpole" hydrogens are located on
A)the same carbon B)adjacent carbons
C)C-1 and C-3
D)C-1 and C-4
E)none of the above
Answer: D
Q2) There is something wrong with the following name. Write the structure and correct the name: 2-ethylpropane.
Answer: 11ea7d6e_0662_2035_8568_07790dde7422_TB1830_00_TB1830_00 The correct name is 2-methylbutane.
Q3) 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
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) A mixture of equal amounts of two enantiomers ________.
A)is called a racemic mixture
B)is optically inactive
C)implies that the enantiomers are meso forms
D)both A and B
E)none of the above
Q2) Draw the structure of (2R,3S)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.
Q3) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.
Q4) Provide a careful structure for (2S,3S)-2,3-dibromohexane.
Q5) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
Q6) Which of the following is/are optically inactive?
A)a 50-50 mixture of R and S enantiomers
B)a meso compound
C)every achiral compound
D)a racemic mixture
E)all the above
Q7) Twenty grams of a compound was dissolved in 100 mL of solvent and gave an observed rotation of -20 degrees. The sample tube is 4 dm long. Calculate the specific rotation.
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Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
Q2) How many carbons are in the planar double-bond system of 3-methylcyclopentene?
A)0
B)1
C)2
D)3
E)4
Q3) Give the hybridization, shape, and bond angle for a carbon in ethene.
Q4) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one bond?
Q5) Why do reactions tend to proceed at a faster rate as T increases?
Q6) Consider the conversion of C to D via a one-step mechanism. The activation energy of this conversion is 3 kcal/mol. The energy difference between D and the transition state of the reaction is 7 kcal/mol. Estimate H° for the reaction C D.
Q7) The G° for the conversion of "axial" isopropylcyclohexane to "equatorial" isopropylcyclohexane at 298K is -2.1 kcal/mol. Calculate the percentage of isopropylcyclohexane molecules that have the isopropyl substituent in the axial position at this temperature.
[R = 1.987 × 10<sup>-3</sup> kcal mol<sup>-1</sup>K<sup>-1</sup>]
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Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) Which of the following compounds will react most rapidly with HCl?
A)5-methyl-1-hexene
B)4-methyl-1-hexene
C)(E)-5-methyl-2-hexene
D)(E)-2-methyl-3-hexene
E)2-methyl-2-hexene
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) What is the product of the hydrogenation of an alkene?
A)dihaloalkane
B)alkane
C)haloalkane
D)alcohol
E)ether
Page 8
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Chapter 7: Reactions of Alkynes Introduction to Multistep
Synthesis
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Sample Questions
Q1) An optically active compound (A), C<sub>6</sub>H<sub>10</sub>, reacts with H<sub>2</sub>/Ni to produce compound (B), C<sub>6</sub>H<sub>14</sub>. (B)is optically inactive. Deduce the structures of (A)and (B).
Q2) 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>.
Q3) Provide the structure of the major organic produt that results when 2-butyne is treated with 1 equivalent of Br<sub>2</sub>
Q4) Give the IUPAC name for BrCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>2</sub>CH<sub>3</sub>.
Q5) What type of organic product results when 1-butyne is treated with 6M aqueous NaOH?
A)a sodium acetylide
B)an enol
C)an alcohol
D)an aldehyde
E)Not much reaction; most of the alkyne remains unchanged.
Q6) Draw an acceptable structure for 2-hexyne.
Q7) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>. Page 9
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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More
About Molecular Orbital Theory
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Sample Questions
Q1) What compound results from the 1, 4-addition of one equivalent of HBr to 1, 3-butadiene?
A)1-bromo-1-butene
B)2-bromo-2-butene
C)4-bromo-1-butene
D)3-bromo-1-butene
E)1-bromo-2-butene
Q2) Cyclic hydrocarbons which can be represented as structures containing alternating single and double bonds are called ________.
Q3) Due to electron delocalization, one would predict that the carbon-oxygen bond in acetamide, CH<sub>3</sub>CONH<sub>2</sub>, ________.
A)is nonpolar
B)has more double bond character than the carbon-oxygen bond of acetone, (CH<sub>3</sub>)<sub>2</sub>CO
C)is longer than the carbon-oxygen bond of dimethyl ether, (CH<sub>3</sub>)<sub>2</sub>O
D)is longer than the carbon-oxygen bond of acetone, (CH<sub>3</sub>)<sub>2</sub>CO
E)is formed by overlapping sp<sup>3</sup> orbitals
Page 11
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?
A)(R)-2-bromo-3-ethylpentane
B)(S)-2-bromo-3-ethylpentane
C)(R)-3-bromo-2-methylpentane
D)(S)-3-bromo-2-methylpentane
E)3-bromo-3-ethylpentane
Q2) Which of the following is the best nucleophile in water?
A)I<sup>-</sup>
B)CH<sub>3</sub>SCH<sub>3</sub>
C)CH<sub>3</sub>OCH<sub>3</sub>
D)Cl<sup>-</sup>
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) Do all primary alkyl iodides undergo S<sub>N</sub>2 reactions with sodium cyanide in DMSO at identical rates? Explain.
Page 12
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Sample Questions
Q1) Which of the following correctly reflects relative stabilities of carbocations?
A)3° allylic > 2° > 1° benzylic
B)methyl > 2° benzylic > 3°
C)3° benzylic > vinyl > 1°
D)2° allylic > 2° > vinyl
E)1° benzylic > 3° > 3° allylic
Q2) Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.
Q3) Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?
A)1-chloropentane
B)2-chloropentane
C)3-chloropentane
D)1-chloro-2-methylbutane
E)1-chloro-3-methylbutane
Q4) Show the best way to prepare CH<sub>3</sub>OCH(CH<sub>3</sub>)<sub>2</sub> by an S<sub>N</sub>2 reaction.
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Q5) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
Chapter 11: Reactions of Alcohols, Ethers, Epoxides,
and Sulfur-Containing Compounds
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Sample Questions
Q1) Why are alcohols typically poor electrophiles?
Q2) Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl<sub>2</sub>)?
A)(CH<sub>3</sub>)<sub>3</sub>COH
B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH
C)CH<sub>3</sub>CHOHCH<sub>2</sub>CH<sub>3</sub>
D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH
Q3) When dipentyl ether is treated with excess HI, through what type of mechanism(s)does the major product result?
A)S<sub>N</sub>2
B)S<sub>N</sub>1
C)both S<sub>N</sub>1 and S<sub>N</sub>2
D)E1
E)E2
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>
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Chapter 12: Organometallic Compounds
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Sample Questions
Q1) How would one use a Grignard-based synthesis to accomplish the following transformation?
benzyl bromide (PhCH<sub>2</sub>Br)to 3-phenyl-1-propanol
Q2) Provide the structure of the major organic product that results when 1-bromocyclohexene reacts with metallic magnesium in diethyl ether.
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) Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain briefly.
Q5) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q6) Complete and balance the following reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li + CuI
Q7) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q8) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + SiCl<sub>4</sub>
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Q9) Name the organic products that would result from metathesis of 1,8-nonadiene.
Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) 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
Q2) Provide the structure of semiquinone radical.
Q3) Which of the following represents the best preparation of 2-cyclopentenol from cyclopentane?
A)1) Br<sub>2</sub>, h 2. NaOCH<sub>3</sub> 3. NBS, CCl<sub>4</sub> 4. H<sub>2</sub>O
B)1) NBS, CCl<sub>4</sub> 2. Br<sub>2</sub>, CCl<sub>4</sub> 3. NaOH
C)1) Br<sub>2</sub>, h 2. H<sub>2</sub>O<sub>2</sub>
D)1) NBS, CCl<sub>4</sub> 2. NaOCH<sub>3</sub> 3. H<sub>2</sub>O<sub>2</sub>
E)1) NBS, CCl<sub>4</sub> 2. H<sub>2</sub>O2 3. Br<sub>2</sub>, CCl<sub>4</sub> 4. NaOCH<sub>3</sub>
Q4) Explain how CFCs are linked to depletion of stratospheric ozone.
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) What does "m/z" stand for and what does it mean?
Q2) 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>
Q3) Is the <sub>max</sub> of phenol in aqueous solution affected by the pH of the solution? If so, explain how and why <sub>max</sub> changes.
Q4) In the mass spectrum of bromoform, CHBr<sub>3</sub>, molecular ion peaks appear at m/z 250, 251, 252, and 253? What is the ratio of the intensities of these peaks?
A)1:1:1:1
B)1:2:2:1
C)1:3:3:1
D)2:3:3:2
E)3:2:2:3
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>
Q6) Is it possible to have an M + 2 peak in mass spectrometry? Explain.
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Chapter 15: Nmr Spectroscopy
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Sample Questions
Q1) Which of the following spectroscopic techniques uses the lowest energy of the electromagnetic radiation spectrum?
A)UV
B)visible
C)IR
D)X-ray
E)NMR
Q2) Why is carbon-hydrogen coupling not generally seen in <sup>1</sup>H NMR spectra?
Q3) H-H coupling is observed in the <sup>1</sup>H NMR spectrum of CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub> and the signal from the methylene H's does not appear as a single peak. How does this signal appear? Explain in detail what is occurring.
Q4) What multiplicities are observed in the spin coupled <sup>13</sup>C NMR spectrum of 2,3-dimethyl-2-butene?
Q5) Predict the number of signals expected, their splitting, and their relative area in the <sup>1</sup>H NMR spectrum of 1,2-dichloroethane (ClCH<sub>2</sub>CH<sub>2</sub>Cl).
Q6) Which of the following compounds has a signal disappear when D<sub>2</sub>O is added to it, ethyl alcohol or ethyl chloride?
Page 18
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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Sample Questions
Q1) Which of the following is (are)formed in the reaction between ethyl butanoate and ethyl amine?
A)ethanol
B)1-butanol
C)N-ethylbutanamide
D)both A and C
E)both B and C
Q2) Propose a synthesis of benzonitrile from benzene and any other necessary reagents.
Q3) What are the products of the reaction of benzoic acid with thionyl chloride?
Q4) Esters and amides are most easily made by nucleophilic acyl substitution reactions on ________.
A)alcohols
B)acid anhydrides
C)carboxylates
D)carboxylic acids
E)acid chlorides
Q5) Provide the proper IUPAC name for (CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CH(CN)CH<sub>3</s ub>.
Q6) Provide the structure of propanoic anhydride. Page 19
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Chapter 17: Reactions of Aldehydes and Ketones
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Q1) Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.
Q2) Provide the structure of the acetal that results when 4-heptanone is dissolved in methanol containing an acid catalyst.
Q3) List the following carbonyl compounds in order of decreasing reactivity toward nucleophiles: ester, acid chloride, amide, aldehyde, ketone.
Q4) In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemical shift ranges below?
A)1)0-2.0 ppm
B)2)0-3.0 ppm
C)4)0-4.5 ppm
D)7)0-8.0 ppm
E)9)0-10.0 ppm
Q5) Provide the structure of the cyanohydrin that results when cyclopentanone reacts with HCN.
Q6) By which single-step process can benzene be readily converted into acetophenone?
Q7) Propose a sequence of steps to convert propyne to 4-heptanol.
Page 21
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Sample Questions
Q1) List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione, diethyl malonate, propanal, ethyl acetate.
Q2) Which compound's H is the least acidic?
A)nitroethane
B)propanenitrile
C)N,N-dimethylacetamide
D)propanal
E)acetone
Q3) Provide a detailed, stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.
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) Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.
Q6) 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.
Page 22
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Sample Questions
Q1) Which of the following is the electrophile that attacks the aromatic ring during sulfonation?
A)HSO<sub>3</sub><sup>+</sup>
B)SO<sub>2</sub><sup>+</sup>
C)HSO<sub>3</sub><sup>-</sup>
D)H<sub>2</sub>SO<sub>4</sub>
E)HSO<sub>4</sub><sup>-</sup>
Q2) Why must Friedel-Crafts acylation reactions be run with more than a single equivalent of AlCl<sub>3</sub>?
Q3) Can one distinguish among the three isomeric xylenes using <sup>13</sup>C NMR? Explain.
Q4) Explain why direct nitration of aniline yields, among other products, m-nitroaniline.
Q5) Provide a detailed, stepwise mechanism for the reaction of benzene with Br<sub>2</sub> and FeBr<sub>3</sub>. Make sure to include the activating reaction between Br<sub>2</sub> and FeBr<sub>3</sub> in your mechanism.
Q6) Provide a series of synthetic steps by which p-bromoanisole can be prepared from benzene.
Page 23
Q7) What sequence of reagents can be used to make m-bromobutylbenzene from benzene?
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Chapter 20: More About Amines Heterocylic Compounds
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Q1) Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.
Q2) Draw 2-methylpyrrolidine.
Q3) Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.
Q4) Provide a structural representation of oxetane.
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
Q6) Draw 4-methylisoquinoline.
Q7) Provide the structure of thymine; How is it used by organisms?
Q8) When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?
A)2-position
B)3-position
C)4-position
Q9) Draw the structure of piperidine.
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Chapter 21: Carbohydrates
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Q1) All chiral D-sugars rotate plane-polarized light ________.
A)clockwise
B)counterclockwise
C)+20.0°
D)in a direction that cannot be predicted but must be determined experimentally
E)since they are optically inactive
Q2) Which of the following statements best describes the meaning of mutorotation?
A)a rapid exchange between the and forms of diasternomeric sugars
B)a rapid exchange between the D and L forms
C)a slow exchange between hydrogen and deuterated hydrogen
D)a slow change in optical rotation to reach an equilibrium value
E)a slow change in absolute configuration to reach an equilibrium value
Q3) Provide the structure of the more stable chair conformer which results when -D-galactose is treated with excess acetic anhydride/pyridine.
Q4) An optically active D-aldopentose A produced an optically active alditol B upon treatment with sodium borohydride. When this aldopentose was subjected to a Ruff degradation, a D-aldotetrose C was generated. This aldotetrose yielded an optically inactive aldaric acid D upon oxidation with nitric acid. Use these data to provide the structures of compounds A, B, C, and D.
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) Treatment of a decapeptide with Edman's reagent releases PTH-Ala. What conclusion can be drawn regarding the decapeptide's primary structure?
Q2) Draw the form of L-lysine which is present at biological pH.
Q3) Explain the importance of the Merrifield method in peptide synthesis.
Q4) Provide the structure of Ala-Ser-Gly at biological pH.
Q5) Draw and name the amino acids which may be described as heterocyclic.
Q6) In conventional peptide synthesis, the nitrogen of a given amino acid must be deactivated or blocked while the carboxyl group is activated. Which of the following reagents is used to protect the amino group of an amino acid?
A)di-tert-butyl dicarbonate
B)dicyclohexylcarbodiimide
C)ninhydrin
D)trifluoroacetic acid
E)phenylisothiocyanate
Q7) Draw the predominant form of aspartate at physiological pH.
Q8) Provide the structure of the tripeptide val-gly-ser at biological pH.
Q9) Draw the form of L-tryptophan which is present at biological pH.
Q10) Provide the structure of the tripeptide glu-ser-ala at pH 12.
Q11) How is the enzyme chymotrypsin used in peptide structure determination? Page 26
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Chapter 23: Catalysis
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Q1) 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.
Q2) Which of the following residues acts as a general-base catalyst in the cleavage of the C<sub>3</sub>-C<sub>4</sub> bond in the mechanism of the aldolase-catalyzed reaction?
A)methionine
B)histidine
C)cysteine
D)asparagine
E)lysine
Q3) Which of the following statements is/are true about catalysts?
A)They can be used only once.
B)They participate in the chemical reaction, but are not changed or consumed.
C)They change the stability of reactants and products.
D)They change the amount of product formed in a chemical reaction.
E)all of the above
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) What are holoenzymes and apoenzymes?
Q2) Give the purpose of thymidylate synthase.
A)converts cytosine to guanine
B)converts guanine to cytosine
C)converts thymine to uracil
D)converts uracil to thymine
E)converts adenine to guanine
Q3) What metal ion is also required by biotin-dependent enzymes?
Q4) Which of the following is not true about catabolic reactions?
A)Catabolic reactions require NAD<sup>+</sup> for a coenzyme.
B)Catabolic reactions are most often oxidation reactions.
C)Catabolic reactions are most often reduction reactions.
D)Catabolic reactions require an oxidizing coenzyme.
E)Catabolic reactions break down complex molecules into simpler ones.
Q5) A deficiency of ________ results in megoblastic anemia.
A)folic acid
B)thiamine
C)niacin
D)riboflavin
E)vitamin D
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Chapter 25: The Chemistry of Metabolism
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Q1) To what reaction are many endergonic metabolic processes coupled in order to make them exergonic?
Q2) Provide the structure of -farnesene, a simple, acyclic sesquiterpene.
Q3) a-Ketoglutarate is an intermediate in the citric acid cycle. Draw its structure.
Q4) In glycolysis, what type of reaction converts the 6-carbon intermediate into two 3-carbon intermediates?
A)reverse aldol condensation
B)reverse Claisen condensation
C)a reverse Michael addition
D)a reverse Diels Alder reaction
E)a transesterification reaction
Q5) At biological pH, ADP has ________ negative charges per molecule.
A)4)0
B)3)3
C)2)8
D)1)1
E)0)6
Q6) 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.
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) Draw the structure of ATP.
Q2) Describe how RNA is easily cleaved.
Q3) Draw the structure of UDP.
Q4) What is the composition of a ribosome?
A)40% protein, 60% rRNA
B)60% protein, 40% tRNA
C)40% protein, 60% tRNA
D)40% protein, 60% mRNA
E)100% protein, 0% rRNA
Q5) Why is the G°' value for the hydrolysis of ATP large and negative? Give three reasons.
Q6) Which of the following bases distinguish DNA from RNA?
A)adenine and cytosine
B)guanine and uracil
C)thymine and uracil
D)uracil and guanine
E)adenine and thymine
Q7) Give the final product of an amino acid reacting with ATP, then t-RNA.
Q8) Show the hydrogen bonding which occurs when guanine and cytosine form a base pair.
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Chapter 27: Synthetic Polymers
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Q1) Draw the structure of the polymer that results when methyl -cyanoacrylate undergoes polymerization. By what name is this polymer commonly known?
Q2) In a recycling symbol, the ________ the number in the middle of the symbol, the more easily the compound can be recycled.
Q3) Which of the following is more likely to form non-terminated polymeric chains called living polymers?
A)cationic polymerization
B)free radical polymerization
C)anionic polymerization
D)A and B
E)A and C
Q4) Draw a short segment of neoprene, using four monomers.
Q5) Name the monomer used in the production of neoprene.
Q6) Describe what thermoplastic polymers are.
Q7) List the two major classes of synthetic polymers and give one example of each.
Q8) What are crystallites?
Q9) Show how branching could occur during the free-radical polymerization of styrene.
Q10) ABS is a copolymer of what three monomers?
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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) Give the conditions for 1,3-hydrogen shifts.
A)suprafacial rearrangement
B)antarafacial rearrangement
C)thermal conditions
D)photochemical conditions
E)all of the above
Q3) In the allyl radical, which molecular orbital is singly occupied?
A)the bonding molecular orbital
B)the nonbonding molecular orbital
C)the antibonding molecular orbital
D)none of the above
Q4) What are the three most common pericyclic reactions? Give examples.
Q5) Give a representation of the bonding molecular orbital of the allyl cation.
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