Materials Chemistry
Exam Review
Course Introduction
Materials Chemistry explores the chemical principles underlying the design, synthesis, characterization, and application of materials. The course covers the relationship between molecular structure and macroscopic properties, examining metals, ceramics, polymers, composites, and nanomaterials. Students will learn about methods for controlling material properties through chemical processes, the fundamentals of solid-state chemistry, and how innovations in materials drive advancements in technology, energy, and sustainability. Laboratory components and case studies emphasize real-world applications and the development of novel materials for electronic, magnetic, biomedical, and environmental uses.
Recommended Textbook
Organic Chemistry 7th 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) The N-H bond in the ammonium ion, NH<sub>4</sub><sup>+</sup>, is formed by the overlap of what two orbitals?
A)sp<sup>3</sup>-sp<sup>3</sup>
B)sp<sup>3</sup>-sp<sup>2</sup>
C)sp<sup>2</sup>-sp<sup>2</sup>
D)sp<sup>2</sup>-s
E)sp<sup>3</sup>-s
Answer: E
Q2) Among the hydrogen halides, the strongest bond is found in ________ and the longest bond is found in ________.
A)HF, HF
B)HF, HI
C)HI, HF
D)HI, HI
E)HCl, HBr
Answer: B
Q3) Draw the Kekulé structure for each of the following: a. CH<sub>3</sub>CH<sub>2</sub>OH b. CH<sub>3</sub>CHO c. (CH<sub>3</sub>)<sub>3</sub>C<sup>+</sup>
Answer: 11ea7d6e_065b_4237_8568_31f3951f6548_TB1830_00_TB1830_00
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) If H<sub>2</sub>O has a pK<sub>a</sub> value of 15.7 and HF has a pK<sub>a</sub> value of 3.2, which is a stronger base, HO<sup>-</sup> or F<sup>-</sup>? Explain.
Answer: HO<sup>-</sup> is a stronger base than F<sup>-</sup> because HF is a stronger acid than H<sub>2</sub>O, and the stronger the acid the weaker its conjugate base.
Q2) Which of the following is not a conjugate acid-base pair?
A)"H<sub>2</sub>O, HO<sup>-</sup>"
B)"H<sub>2</sub>O, H<sub>3</sub>O<sup>+</sup>"
C)"HSO<sub>4</sub><sup>-</sup>, H<sub>2</sub>SO<sub>4</sub>" D)"<sup>-</sup>OH, O<sup>2-</sup>"
E)"NO<sub>3</sub><sup>-</sup>, NO<sub>2</sub><sup>-</sup>"
Answer: E
Q3) What is the conjugate acid 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: A
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Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?
A)n
B)n + 2
C)n - 2
D)2n
E)2n + 2
Answer: E
Q2) Give the structure of tetramethylammonium chloride.
Answer: 11ea7d6e_0665_7bc0_8568_7778d1aa6cd6_TB1830_00_TB1830_00
Q3) Which compound is more soluble in water? Briefly explain your choice. (CH<sub>3</sub>)<sub>2</sub>NH or CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub>
Answer: (CH<sub>3</sub>)<sub>2</sub>NH is more soluble in water since it can hydrogen bond with water. Alkanes are not capable of hydrogen bonding with water.
Q4) Draw the structure of N-ethyl-5-methyl-3-hexanamine.
Answer: 11ea7d6e_0665_7bc1_8568_5b2154bacfb6_TB1830_00_TB1830_00
Q5) Provide a representation of the gauche conformer of butane.
Answer: 11ea7d6e_0667_c5c3_8568_03dc6e43ae7c_TB1830_00_TB1830_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?
A)0
B)1
C)2
D)3
E)4
Q2) Consider the molecules with molecular formula
C<sub>2</sub>H<sub>2</sub>Br<sub>2</sub>Cl<sub>2</sub>.
a) Draw a structure that is optically inactive because it does not have an asymmetric center.
b) Draw a structure that is optically inactive because it is a meso compound.
c) Draw a structure that is optically active because it is chiral.
Q3) Which of the following is a meso compound?
A)trans-1, 4-dimethylcyclohexane
B)cis-1, 3-dimethylcyclohexane
C)trans-1, 3-dimethylcyclohexane
D)cis-1, 4-dimethylcyclohexane
E)trans-1, 2-dimethylcyclohexane
Q4) Draw the stereoisomers of 1,3-dichlorocyclopentane.
Q5) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.
Page 6
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Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Draw and name the six alkenes which have the molecular formula
C<sub>5</sub>H<sub>10</sub>.
Q2) Give the general formula for a cyclic alkene.
A)C<sub>n</sub>H<sub>2n-4</sub>
B)C<sub>n</sub>H<sub>2n-2</sub>
C)C<sub>n</sub>H<sub>2n</sub>
D)C<sub>n</sub>H<sub>2n+2</sub>
Q3) Draw the curved arrows to show how CH<sub>3</sub>CH=CHCH<sub>3</sub> reacts with HBr to form a carbocation.
Q4) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.
Q5) 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
Q6) Give the hybridization, shape, and bond angle for a carbon in ethene.
Q7) Draw the structure of propyl vinyl ether.
Q8) Draw (E)-2-methyl-3-hexen-1-ol.
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Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) What is the product of the hydrogenation of an alkene?
A)dihaloalkane
B)alkane
C)haloalkane
D)alcohol
E)ether
Q2) What is hyperconjugation, and how does it affect carbocation stability?
Q3) Which statement is true in the oxymercuration-reduction 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)Markonikov orientation and both syn and anti addition occur.
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
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Chapter 7: Reactions of Alkynes Introduction to Multistep
Synthesis
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Sample Questions
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) Provide the structure of all distinct terminal alkynes with a molecular formula of C<sub>6</sub>H<sub>10</sub>.
Q4) Why are terminal alkynes more acidic than other hydrocarbons?
Q5) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q6) Describe a sequence of reactions by which trans-2-pentene can be prepared from propyne.
Q7) Draw an acceptable structure for acetylene.
Q8) Give the IUPAC name for HCCCH<sub>2</sub>CH<sub>2</sub>CH<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) Which MOs are bonding MOs in the ground state of 1,3,5-hexatriene?
Q2) Draw the LUMO of 1,3,5-hexatriene.
Q3) When cycloheptatriene is deprotonated, an anion with seven resonance forms of equal energy can be drawn. Given this fact, explain why cycloheptatriene is only slightly more acidic than propene.
Q4) Which of the following statements about benzene is correct?
A)All of the carbon atoms are sp<sup>3</sup> hybridized.
B)It has no delocalized electrons.
C)The carbon-carbon bond length is longer than that of ethane.
D)It is a planar molecule.
E)The carbon-hydrogen bonds are not the same length.
Q5) Which of the following is aromatic?
A)cyclopentadienyl cation
B)1,3-cyclohexadiene
C)cyclobutenyl anion
D)1,3,5-hexatriene
E)cycloheptatrienyl cation
Q6) Stabilization of a charged species usually happens when this species can be more accurately depicted as a hybrid of several resonance contributing forms. Why is this the case? Page 11
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Identify the strongest nucleophile in an S<sub>N</sub>2 reaction.
A)isopropoxide ion
B)tert-butoxide ion
C)ethoxide ion
D)tert-pentoxide ion
Q2) Assuming no other changes, what is the effect of doubling both the concentration of the alkyl halide and the nucleophile in the above reaction?
A)no change
B)doubles the rate
C)triples the rate
D)quadruples the rate
E)rate is halved
Q3) When nucleophile and leaving group are contained in the same molecule, is intermolecular or intramolecular reaction favored? Explain.
Q4) Provide a detailed, stepwise mechanism for the reaction below.
(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>I + CN<sup>-</sup>
(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CN + I<sup>-</sup>
Q5) Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?
Page 13
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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 is least likely to be found in the product mixture which results when 2-iodopentane reacts with sodium ethoxide in ethanol?
A)1-ethoxypentane
B)2-ethoxypentane
C)(Z)-2-pentene
D)(E)-2-pentene
E)1-pentene
Q2) Which of the following halides is most 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
Q3) 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
Page 14
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Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds
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Sample Questions
Q1) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>CH<sub>2</sub>OH + HBr
Q2) When 1-pentanol is heated with HCl/ZnCl<sub>2</sub>, 1-chloropentane is the major organic product. This reaction proceeds through an ________ mechanism, and ________ is produced as a byproduct.
A)S<sub>N</sub>1, H<sub>2</sub>O
B)S<sub>N</sub>2, H<sub>2</sub>O
C)S<sub>N</sub>1, H<sub>2</sub>
D)S<sub>N</sub>2, H<sub>2</sub>
E)E2, H<sub>2</sub>
Q3) 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).
Q4) How are certain arene oxides believed to cause cancer?
Q5) Why are alcohols typically poor electrophiles?
Q6) Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in the presence of HBr.
Page 15
Q7) Draw the tosylate ion and explain why it is a particularly good leaving group.
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Chapter 12: Organometallic Compounds
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Sample Questions
Q1) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
Q2) Name the three major aklene products that result when 1-pentene is treated with Grubbs catalyst.
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) Provide the structure of the major organic product that results when 1-bromocyclohexene reacts with metallic magnesium in diethyl ether.
Q5) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q6) List the sequence of reagents necessary to prepare the appropriate Gilman reagen from ethyl iodide.
Q7) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q8) 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 16
Q9) Name the organic products that would result from metathesis of 1,8-nonadiene.
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.
Q2) How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.
Q3) Explain how CFCs are linked to depletion of stratospheric ozone.
Q4) Name each distinct alkyl chloride (including stereoisomers)that can be generated from monochlorination of 2,2-dimethylbutane.
Q5) 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
Q6) An unknown sample is suspected of being either ethane or isobutane. How would you distinguish between the two alkanes?
Q7) Write the structures of all of the monobromination products of 1,1,3,3-tetramethylcyclobutane.
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) Describe the fate of a molecule from introduction to detection in a mass spectrometer.
Q2) Which molecule below has a significant band in the 1720 - 1780 cm<sup>-1</sup> range of its IR spectrum?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
B)CH<sub>3</sub>C CCH<sub>2</sub>CH<sub>3</sub>
C)CH<sub>3</sub>CH<sub>2</sub>CH(NH<sub>2</sub>)CH<sub>3</sub>
D)(CH<sub>3</sub>)<sub>3</sub>N
E)CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
Q3) 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>
Q4) How could IR spectroscopy be used to distinguish between the following pair of compounds?
CH<sub>3</sub>OCH<sub>2</sub>CH<sub>3</sub> and CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
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Q5) How can UV spectroscopy be used to estimate the nucleotide composition of DNA?
Chapter 15: Nmr Spectroscopy
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Sample Questions
Q1) 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).
Q2) Provide the structure that is consistent with the data below. C<sub>7</sub>H<sub>14</sub>O<sub>2</sub> IR (cm<sup>-1</sup>): 2950, 1750 <sup>1</sup>H NMR (d): 2.3 (2H, q), 1.0 (3H, t), 0.9 (9H, s) <sup>13</sup>C NMR (d): 185 (s), 78 (s), 29 (t), 14 (q), 12 (q)
Q3) A compound gave a signal at 203 ppm in the <sup>13</sup>C NMR spectrum. How would it be possible to tell if the compound is an aldehyde or a ketone in a proton-coupled <sup>13</sup>C NMR spectrum?
Q4) Can alkenes and aromatics be easily distinguished from each other in an <sup>13</sup>C NMR spectrum?
Q5) 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.
Q6) What information does a COSY spectrum give?
Q7) What information does a HETCOR spectrum give?
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Q8) Give one reason why <sup>13</sup>C NMR is less sensitive than <sup>1</sup>H NMR.
Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Q1) 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
Q2) How are acyl phosphates produced in the body? What organic byproduct results?
Q3) Provide a detailed, stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.
Q4) In an MO depiction of the carbonyl's reactivity with an amine nucleophile, the most important MO overlap occurs between the amine's lone pair and the carbonyl's
A) <sub>c-</sub><sub>o</sub>
B) *<sub>c-o</sub>
C) <sub>c-o</sub>
D) *<sub>c-o</sub>
E)n<sub>o</sub>
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Chapter 17: Reactions of Aldehydes and Ketones
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Sample Questions
Q1) Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.
Q2) In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.
A)20 ppm
B)40 ppm
C)60 ppm
D)120 ppm
E)200 ppm
Q3) Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.
Q4) By which single-step process can benzene be readily converted into acetophenone?
Q5) An unknown compound (A), C<sub>10</sub>H<sub>12</sub>O, gave the following proton NMR data:
(a)triplet, at 1.0 ppm (3H)
(b)quartet, at 2.4 ppm (2H)
(c)singlet, at 3.7 ppm (2H)
(d)multiplet, at 7.2 ppm (5H)
Propose a structure for (A).
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Sample Questions
Q1) Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?
A)lithium hydroxide
B)lithium diisopropylamide
C)methyllithium
D)diethylamine
E)pyridine
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) 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) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
Page 22
Q5) Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Sample Questions
Q1) Benzene can be reduced to cyclohexane when it is treated with hydrogen in the presence of a nickel catalyst under conditions of high temperature and pressure. Predict the signs of H° and S° for this process.
A) H° > 0, S° > 0
B) H° > 0, S° < 0
C) H° > 0, S° = 0
D) H° < 0, S° > 0
E) H° < 0, S° < 0
Q2) Provide the structure of dibenzyl ether.
Q3) 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.
Q4) Can one distinguish among the three isomeric xylenes using <sup>13</sup>C NMR? Explain.
Q5) Provide a series of synthetic steps by which p-bromoanisole can be prepared from benzene.
Q6) Why does benzene undergo electrophilic substitution rather than electrophilic addition?
Page 23
Q7) Draw benzyl bromide.
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Chapter 20: More About Amines Heterocylic Compounds
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Q1) Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.
Q2) Show how the dipole moments are oriented in pyrrolidine and pyrrole, and explain why they are oriented in opposite directions.
Q3) Draw the structures of piperidine and morpholine and explain their relative basicities.
Q4) Provide the structure of thymine; How is it used by organisms?
Q5) Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.
Q6) Draw 4-methylisoquinoline.
Q7) Provide a structural representation of oxetane.
Q8) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Q9) When benzofuran is treated with acetic anhydride, the major organic product is
A)2-acetylbenzofuran
B)3-acetylbenzofuran
C)4-acetylbenzofuran
D)5-acetylbenzofuran
E)7-acetylbenzofuran
Q10) Draw 2-methylpyrrolidine.
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Chapter 21: Carbohydrates
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Q1) Which of the following is true about sucrose?
A)It hydrolyzes to fructose and glucose.
B)It is a reducing sugar.
C)It is a monosaccharide.
D)It undergoes mutorotation in water.
Q2) When a monosaccharide reacts to give the pyranose form from its open-chain form, how many distinct pyranose forms are possible?
A)1
B)2
C)2<sup>n</sup>, where n is the number of carbons present D)4n + 2, where n is the number of carbons present E)4
Q3) 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.
Q4) Provide the structure of the more stable chair conformer which results when -D-galactose is treated with excess acetic anhydride/pyridine.
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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) How is the enzyme chymotrypsin used in peptide structure determination?
Q3) Which of the following are capable of denaturing proteins?
A)organic solvents
B)detergents
C)extreme pH
D)heat
E)all of the above
Q4) Draw vertical lines through the peptide bonds in the decapeptide below that will be cleaved by cyanogen bromide.
Try-Ser-Ala-Met-Ser-Pro-Met-Gly-Gly-Asp
Q5) When a disulfide linkage is formed, the compound containing this new linkage has been ________.
A)hydrolyzed
B)dehydrated
C)electrolyzed
D)oxidized
E)reduced
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Chapter 23: Catalysis
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Q1) Which of the following statements about how acid catalyzes the hydrolysis of esters is (are)correct?
A)The acid catalyst increases the rate of formation of the tetrahedral intermediate by protonating the carbonyl and thereby increasing the reactivity of the carbonyl group.
B)The acid catalyst increases the rate of the reaction by changing the basicity of the group eliminated when the tetrahedral intermediate collapses.
C)The acid catalyst protonates the water, the nucleophile in the reaction, and thereby makes it a stronger nucloephile.
D)both A and B
E)all of the above
Q2) How does a metal catalyst increase the rate of reaction?
Q3) Describe the reaction coordinate diagram for a specific-acid-catalyzed reaction.
A)one peak
B)two peaks, second peak is larger
C)two peaks, second peak is smaller
D)two peaks, equal size
E)three peaks, middle peak is larger
Q4) Explain what is meant by the induced fit model. Give an example.
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) The common name of vitamin B<sub>1</sub> is ________.
A)niacin
B)riboflavin
C)thiamine
D)biotin
E)panthothenate
Q2) 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
Q3) Which of the following statements regarding glycolysis is correct?
A)Glycolysis is another name for the Krebs cycle.
B)Disaccharides can enter glycolysis without being hydrolyzed.
C)Glycolysis occurs primarily in the fluid outside the cell.
D)Glycolysis is the series of reactions which produces 2 moles of pyruvate from each mole of D-glucose.
E)Glycolysis is the series of reactions which is responsible for the complete oxidation of pyruvate and acetyl-CoA to carbon dioxide.
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Chapter 25: The Chemistry of Metabolism
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Q1) In which stage of catabolism is the citric acid cycle found?
Q2) Complete the following concerning ATP's role as the universal carrier of chemical energy: "The energy ________ from the hydrolysis of ATP converts ________ reactions into ________ reactions."
A)released, exergonic, endergonic
B)released, endergonic, exergonic
C)consumed, exergonic, endergonic
D)consumed, endergonic, exergonic
E)consumed, oxidation, reduction
Q3) Identify the first 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) Which step of the b-oxidation pathway is a conjugate addition of water to the organic substrate?
Q5) What class of enzyme puts a phosphoryl group on its substrate?
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) Show that you understand how the structural components of DNA are bonded together by drawing a linear segment that contains 3 base residues.
Q2) Propose a mechanism for the conversion of D-glucose to D-glucose-6-phosphate using ATP as a source of the phosphate.
Q3) Give the order for base pairing for the following strand. G-C-A-T-T-C-C-G-A-T
A)C-G-U-A-A-G-G-C-U-A
B)U-G-T-A-A-G-G-U-T-U
C)A-T-G-C-C-T-T-A-G-C
D)T-A-C-G-G-A-A-T-C-G
E)C-G-T-A-A-G-G-C-T-A
Q4) In an entire DNA strand, what percentage consists of genetic information and what percentage consists of introns?
A)98% genetic information, 2% introns
B)2% genetic information, 98% introns
C)50% genetic information, 50% introns
D)100% genetic information, 0% introns
E)99% genetic information, 1% introns
Q5) Draw the structure of dTTP.
Q6) What is a nucleoside? Give an example.
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Chapter 27: Synthetic Polymers
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Q1) Give the monomer for the polymer teflon.
A)propylene
B)acrylonitrile
C)tetrafluoroethylene
D)poly(vinyl acetate)
E)styrene
Q2) Natural rubber is a ________.
A)polyamide
B)polyester
C)polycarbonate
D)polyurethane
E)none of the above
Q3) What are thermosetting polymers?
Q4) List the two main groups of polymers and give one example of each.
Q5) Show the mechanism for the formation of a segment of polystyrene containing two molecules of styrene and initiated by hydrogen peroxide.
Q6) 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?
Q7) Draw a short segment of neoprene, using four monomers.
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Chapter 28: Pericyclic Reactions
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Q1) Which of the following statements best describes the term suprafacial?
A)formation of two sigma bonds from the same side of the pi system
B)formation of two pi bonds from the same side of the sigma system
C)formation of two sigma bonds from opposite sides of the pi system
D)formation of two pi bonds from opposite sides of the sigma system
E)an anti cycloaddition
Q2) When an allyl anion undergoes a cycloaddition under thermal conditions with ethylene (bonds forming at the ends of the -systems), the cycloaddition is described as ________.
A)[2+2] and suprafacial
B)[2+4] and suprafacial
C)[2+2] and antarafacial
D)[2+4] and antarafacial
E)[2+3] and antarafacial
Q3) Give a representation of the antibonding molecular orbital of the allyl anion.
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.
Q5) Under photochemical conditions, is an [2+2] cycloaddition suprafacial or antarafacial?
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