Pharmaceutical Chemistry Exam Review - 2928 Verified Questions by Quizplus

Pharmaceutical Chemistry

Exam Review

Course Introduction

Pharmaceutical Chemistry focuses on the study of drug design, development, and analysis, integrating principles from chemistry, biology, and pharmacology to understand the mechanisms by which drugs interact with biological systems. The course covers topics such as the chemical structure of pharmaceuticals, structure-activity relationships, drug metabolism, methods of synthesis, and analytical techniques for assessing drug purity and quality. Emphasis is placed on the practical application of chemical knowledge to discover, optimize, and evaluate new therapeutic agents, preparing students for roles in drug development, regulatory affairs, and clinical research within the pharmaceutical industry.

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) What orbitals are used to form the covalent bonds in butane (CH3CH2CH2CH3)?

Answer: The carbon-carbon bonds are formed by the overlap of two carbon sp3 hybrid atomic orbitals. The carbon-hydrogen bonds are formed by the overlap of a carbon sp3 hybrid atomic orbital and a hydrogen s orbital.

Q2) In what type of orbital are the lone pair electrons of methoxide (CH3O-)found ?

A)s

B)p

C)sp

D)sp2

E)sp3

Answer: E

Q3) Draw the shape of a 2p orbital.

Answer: 11ea7d6e_065c_058c_8568_1f16b5a83290_TB1830_00_TB1830_00

Q4) Draw a Lewis structure for the molecule given and show all formal charges. CH2CO

Answer: 11ea7d6e_065b_9059_8568_49c28ece1834_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) Explain why AlCl3 is a Lewis acid.

Answer: A Lewis acid is an electron pair acceptor. Aluminum in AlCl3 has an empty p orbital that can accommodate the pair of electrons provided by a Lewis base.

Q2) Give the conjugate acid and the conjugate base for HSO4-.

Answer: conjugate acid: H2SO4 conjugate base: SO42-

Q3) Which of the following is the strongest acid?

A)HF

B)H2O

C): NH3

D)CH4

E)CH3OH

Answer: A

Q4) 2-Propanol is shown below. Draw the structure of its conjugate base. (CH3)2CHOH

Answer: 11ea7d6e_065f_d637_8568_b5ee2decc99c_TB1830_00_TB1830_00

Q5) 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

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Sample Questions

Q1) Which of the following describes the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane?

A)Both groups are equatorial.

B)Both groups are axial.

C)The tert-butyl group is equatorial and the methyl group is axial.

D)The tert-butyl group is axial and the methyl group is equatorial.

E)none of the above

Answer: C

Q2) Draw the Newman projection that represents the most stable conformation of 3,3-dimethylhexane viewed along the C3-C4 bond.

Answer: 11ea7d6e_0667_508d_8568_89ca08c698db_TB1830_00_TB1830_00

Q3) Which of the following has two equatorial alkyl substituents in its most stable conformation?

A)1,1-dimethylcyclohexane

B)cis-1,2-dimethylcyclohexane

C)cis-1,3-diethylcyclohexane

D)cis-1,4-diethylcyclohexane

E)trans-1,3-diethylcyclohexane

Answer: C

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Page 5

Chapter 4: Isomers: the Arrangement of Atoms in Space

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Sample Questions

Q1) Provide the structure of (R)-4-octanol. Be careful to indicate proper stereochemistry.

Q2) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.

Q3) Briefly describe how two enantiomers might be separated.

Q4) Provide a careful structure for (2S,3R)-2,3-dibromohexane.

Q5) Draw the structure of a meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Q6) Consider the molecules with molecular formula C2H2Br2Cl2.

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.

Q7) Provide a perspective drawing of each diastereomer of (2R,3S)-1,2,3-trichloropentane.

Q8) Can one predict whether a compound with a single asymmetric center is dextro- or levorotatory based on the R/S assignment at this asymmetric center? Explain briefly.

Q9) 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) 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

Q2) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one bond?

Q3) What is the free energy of activation of a one-step reaction? How is it qualitatively related to the rate constant of the reaction?

Q4) Draw the curved arrows to show how CH3CH=CHCH3 reacts with HBr to form a carbocation.

Q5) Draw and name the six alkenes which have the molecular formula C5H10.

Q6) Muscalure, the sex attractant of the common housefly, is an acyclic alkene that contains 23 carbons. How many hydrogen atoms are in a molecule of muscalure?

Q7) Draw vinyl bromide.

Page 7

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Chapter 6: Reactions of Alkenes

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Sample Questions

Q1) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.

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 D2)of cyclohexene.

Q4) Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

A)water + dilute acid

B)water + concentrated acid

C)oxymercuration-demercuration

D)hydroboration-oxidation

E)none of the above

Q5) What is hyperconjugation, and how does it affect carbocation stability?

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Chapter 7: Reactions of Alkynes Introduction to Multistep Synthesis

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Sample Questions

Q1) Describe a sequence of reactions by which 3-heptyne can be straightforwardly prepared from acetylene.

Q2) The carbon-carbon triple bond of an alkyne is composed of ________.

A)three bonds

B)two bonds and one bond

C)one bond and two bonds

D)three bonds

Q3) 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.

Q4) In the addition of hydrogen bromide to alkynes in the absence of peroxides, which of the following species is believed to be an intermediate?

A)vinyl anion

B)vinyl cation

C)vinyl radical

D)carbene

E)bromonium ion

Q5) Why are terminal alkynes more acidic than other hydrocarbons?

Q6) Draw an acceptable structure for 3-sec-butyl-1-heptyne.

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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More

About Molecular Orbital Theory

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Sample Questions

Q1) Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in 4 of the 1, 3, 5-hexatriene system?

A)6

B)5

C)4

D)3

E)0

Q2) Cyclic hydrocarbons which can be represented as structures containing alternating single and double bonds are called ________.

Q3) Which of the following ions is most acidic?

A)C6H5NH3+

B)C6H5CH2NH3+

C)(CH3)2CHNH3+

D)CH3CH2NH3+

E)CH3NH3+

Q4) In the addition of HBr to conjugated dienes, is the product which results from 1,2-addition or that which results from 1,4-addition typically the product of kinetic control?

Q5) Draw (Z)-1,3-hexadiene in its s-trans conformation.

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Chapter 9: Substitution Reactions of Alkyl Halides

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Sample Questions

Q1) Assuming no other changes, what is the effect of doubling only the concentration of the nucleophile in the above reaction?

A)no change

B)doubles the rate

C)triples the rate

D)quadruples the rate

E)rate is halve

Q2) Provide a detailed, stepwise mechanism for the reaction below.

(CH3)2CHCH2CH2CH2I + CN-

(CH3)2CHCH2CH2CH2CN + I-

Q3) Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

A)The substrate is more soluble in polar solvents.

B)The substrate is less soluble in polar solvents.

C)The nucleophile is solvated by polar solvents.

D)Solvation by polar solvents stabilizes the carbocation.

E)Solvation by polar solvents stabilizes the transition state.

Q4) Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?

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Chapter 10: Elimination Reactions of Alkyl Halides

Competition Between Substitution and Elimination

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Sample Questions

Q1) Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Q2) When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3, the more highly substituted alkene product predominates. When KOC(CH3)3 is used instead, the less highly substituted alkene product predominates. Offer an explanation.

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

Q4) 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.

Q5) What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is treated with sodium methoxide in methanol?

Page 12

Q6) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?

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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) A compound (A)C4H10O is optically active. (A)reacts with HCl and ZnCl2 (Lucas test)to form a cloudy product within 10 minutes. Deduce the structure of (A).

Q3) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.

CH3(CH2)6CH2OH + HBr

Q4) Which of the following is least likely to be found in the product mixture which results when 2,2-dimethyl-3-pentanol is heated in phosphoric acid?

A)(E)-4, 4-dimethyl-2-pentene

B)(Z)-4, 4-dimethyl-2-pentene

C)2, 3-dimethyl-2-pentene

D)2, 3-dimethyl-1-pentene

E)4, 4-dimethyl-1-pentene

Q5) Draw the tosylate ion and explain why it is a particularly good leaving group.

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.

Q7) How are certain arene oxides believed to cause cancer?

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Chapter 12: Organometallic Compounds

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Sample Questions

Q1) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.

Q2) Which of the following sequences of reactions would be best when converting cyclohexene oxide into propylcyclohexane?

A)1) CH3CCNa 2. H3O+ B)1) CH3CH2CH2MgBr 2. H2SO4, 3. H2, Pt C)1) H3O+ 2. CH3CCNa D)1) CH3CH2CH2Li 2. HBr E)1) H3PO4, 2. CH3CH2CH2MgBr 3. H+

Q3) What type of intermediate is present when the Grubbs catalyst and a terminal alkene react?

A)metallocyclobutane

B)Grignard reagent

C)Gilman reagent

D)borate ester

E)permanganate ester

Q4) 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) Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-1-heptene.

Q2) Would chlorination or bromination of 2,5-dimethylhexane produce a greater yield of 1-halo-2,5-dimethylhexane?

Q3) How many distinct alkyl chlorides can be obtained from monochlorination of 2,3-dimethylpentane?

A)5

B)8

C)10

D)12

E)16

Q4) When butane undergoes free radical bromination, the product mixture contains 98% 2-bromobutane and 2% 1-bromobutane. How many times more susceptible to hydrogen atom abstraction is a secondary hydrogen in butane than is a primary hydrogen?

A)100

B)73.5

C)50

D)8)7

E)1)5

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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

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Sample Questions

Q1) Which has a lower characteristic stretching frequency, the C=O bond or the C-O bond? Explain briefly.

Q2) Is it possible to have an M + 2 peak in mass spectrometry? Explain.

Q3) Which color is observed when a sample absorbs light at 650 nm?

A)yellow

B)orange

C)red

D)violet

E)greenish-blue

Q4) Which of the following compounds exhibits the pattern of m/z values shown below? 41, 43, 57, 87, 101, 116

A)propylbromide

B)isopropyl bromide

C)sec-butyl isopropyl ether

D)2-hexanol

E)2-butanone

Q5) What does "m/z" stand for and what does it mean?

Page 16

Q6) Show the m/z values of the molecular ion and 5 likely fragments for the compound ethyl ether, CH3CH2OCH2CH3

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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 1H NMR spectrum of (CH3)3CCHO.

Q2) Predict the number of signals expected, their splitting, and their relative area in the 1H NMR spectrum of 1,2-dichloroethane (ClCH2CH2Cl).

Q3) If the frequency for flipping a 1H nucleus at an applied field of 1.4092 Tesla is 60 MHz, what would be the applied magnetic field if the frequency is 360 MHz?

A)8)4552 Tesla

B)0)2349 Tesla

C)1)4092 Tesla

D)4)2577 Tesla

E)3)0439 Tesla

Q4) Deduce the identity of the following compound from the spectral data given. C9H12 : 13C NMR, 21.3 (quartet), 127.2 (doublet), 138.0 (singlet)(ppm)

Q5) What information does a COSY spectrum give?

Q6) What multiplicities are observed in the spin coupled 13C NMR spectrum of 2,3-dimethyl-2-butene?

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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

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Q1) Typically, amides will hydrolyze under ________ conditions than esters.

A)milder

B)more dilute

C)more vigorous

D)less vigorous

E)more saline

Q2) Which of the following best explains why the melting points of saturated fats increase with increasing molecular weight?

A)decreased polarity

B)decreased hydrogen bonding

C)increased hydrogen bonding

D)decreased intermolecular van der Waal's interactions

E)increased intermolecular van der Waal's interactions

Q3) Myristic acid has the formula CH3(CH2)12CO2H. Provide the structure of the triglyceride trimyristin.

Q4) Provide the structure of propanoic anhydride.

Q5) In the lab, a student tried to prepare N,N-diethylacetamide by heating acetyl chloride with two equivalents of triethylamine. Was the student successful? Explain.

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Chapter 17: Reactions of Aldehydes and Ketones

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Q1) Provide the structure of the compound that results when 4-heptanone is treated with peroxyacetic acid.

Q2) Propose a sequence of steps to convert propyne to 4-heptanol.

Q3) By which single-step process can benzene be readily converted into acetophenone?

Q4) Provide the structure of the imine that results when 4-heptanone is treated with CH3CH2CH2NH2 in the presence of an acid catalyst.

Q5) When the carbonyl group of a neutral ketone is protonated,

A)the resulting species becomes more electrophilic.

B)the resulting species is activated toward nucleophilic attack.

C)subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions.

D)the resulting species has a positive charge.

E)all of the above

Q6) Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H2NOH.

Q7) Draw the two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

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Q8) Provide the major organic product of the reaction of aniline with 3-pentanone.

Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds

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Q1) Show how an enolate can add to a carbonyl.

Q2) 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?

Q3) a) The base-catalyzed reaction of 1 mole of acetone with 2 moles of benzaldehyde yields a yellow solid, C17H14O. What is the structure of the product?

b) What will be the result when only 1 mole of benzaldehyde is added?

c) What will be the result when acetone is not added at all?

d) What will be the result when benzaldehyde is not added at all?

e) Why is the self-condensation of acetone unlikely in the presence of benzaldehyde?

Q4) Which of the following could result from the dehydration of an aldol?

A)4-methyl-3-penten-2-one

B)4-methyl-4-penten-2-one

C)4-methyl-5-hexen-2-one

D)4-methyl-4-hexen-2-one

E)3-methyl-4-penten-2-one

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Q5) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.

Chapter 19: Reactions of Benzene and Substituted

Benzenes

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Q1) Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.

Q2) Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions: -OCH3, -OCOCH2CH3, -CH2CH3, -Br.

Q3) Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO3/H2SO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Q4) What factors affect the ortho/para ratio in electrophilic aromatic substitution reactions?

Q5) Provide the structure of benzoic acid.

Q6) In the bromination of benzene using Br2 and FeBr3, is the intermediate carbocation aromatic? Explain.

Q7) Draw p-aminobenzoic acid.

Q8) Which step in the general mechanism for electrophilic aromatic substitution is rate-determining? Explain.

Page 22

Q9) What sequence of reagents can be used to make p-butylbenzenesulfonic acid from benzene?

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Page 23

Chapter 20: More About Amines Heterocylic Compounds

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Q1) Which of the following statements best describes the meaning of the term alkaloid?

A)heterocyclic natural products with a nitrogen as a heteroatom

B)natural, cyclic hydrocarbons

C)heterocyclic natural products with a sulfur as a heteroatom

D)heterocyclic natural products with an oxygen as a heteroatom

E)natural, cyclic hydrocarbons with alkyl groups

Q2) When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?

A)2-position

B)3-position

C)4-position

Q3) Pyridine does not undergo Friedel-Crafts reactions. Offer an explanation.

Q4) Provide the structure of thymine; How is it used by organisms?

Q5) Provide a structural representation of oxetane.

Q6) Draw the structures of the keto forms of both 2-hydroxypyridine and 4-hydroxypyridine.

Q7) Draw 2-methylpyrrolidine.

Q8) What is the stereochemistry of the product in the acid hydrolysis of trans-2,3-epoxybutane?

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Chapter 21: Carbohydrates

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Q1) Which of the following statements best describes the difference between amylose and amylopectin?

A)Amylose is a branched polysaccharide while amylopectin is a chain polysaccharide.

B)Amylose is a straight-chain polysaccharide while amylopectin is a branched polysaccharide.

C)Amylose contains -1,6-glycosidic linkage which amylopectin does not contain.

D)Amylose is composed of thousands of D-glucose units while amylopectin is composed of thousands of D-galactose units.

E)Amylose is one of the largest molecules found in nature while amylopectin is one of the smallest molecules found in nature.

Q2) 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.

Q3) Draw the Fischer projection for the open-chain form of D-erythrose.

Q4) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?

Q5) Is L-glucose the enantiomer of D-glucose, the C-5 epimer of D-glucose, or both?

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Chapter 22: Amino Acids, Peptides, and Proteins

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Q1) Provide the structure of Thr-Gln-Met at pH 7.0.

Q2) In peptide synthesis, give the use of dicyclohexylcarbodiimide.

A)activates the carboxyl group of an amino acid

B)protects the carboxyl group of an amino acid

C)protects the amino group of an amino acid

D)activates the amino group of an amino acid

E)removes the protecting group on the N-terminal amino acid

Q3) Draw the structure of the tetrapeptide Ser-Leu-Phe-Pro at pH 7.0.

Q4) When a disulfide linkage is formed, the compound containing this new linkage has been ________.

A)hydrolyzed

B)dehydrated

C)electrolyzed

D)oxidized

E)reduced

Q5) Provide the structure of the tripeptide glu-ser-ala at pH 12.

Q6) Draw glutamate.

Q7) Draw the predominant form of histidine at pH=0.

Q8) Explain what essential amino acids are and list all of them.

Q9) Explain the importance of the Merrifield method in peptide synthesis. Page 26

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Chapter 23: Catalysis

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Q1) Which of the following are affected when an intramolecular catalyst is used?

A)number of collisions between the two per unit time

B)fraction of collisions with sufficient energy

C)fraction of collisions with proper orientation

D)rate of the reaction

E)all of the above

Q2) Which of the following is not true about metal-ion catalysts?

A)They coordinate with atoms with nonbonded electrons.

B)They can make a reaction center more susceptible to receiving electrons and stabilize a developing charge on the transition state.

C)They can make a leaving group a weaker base and therefore a better leaving group.

D)They act as Lewis bases.

E)They can increase the electrophilicity of a reaction center.

Q3) 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

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Page 28

Chapter 24: The Organic Mechanisms of the Coenzymes

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Q1) How does NAD+ serve as a catalyst in oxidation reactions?

A)It accepts a hydride ion at the 4-position of its pyridinium ring.

B)It accepts a hydride ion at the amide carbonyl group at the 3-position.

C)It accepts a proton at the 4-position of its pyridinium ring.

D)It accepts a proton at the amide carbonyl group at the 3-position.

E)none of the above

Q2) 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.

Q3) Which of the following is/are coenzyme(s)formed from the vitamin niacin?

A)NAD+

B)NADP+

C)NADH

D)NADPH

E)all of the above

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Chapter 25: The Chemistry of Metabolism

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Q1) Draw the structure of pyruvate.

Q2) What compounds are formed when a carboxylate is phosphorylated by the attack at the a-phosphorus of ATP?

Q3) Which of the following is not an intermediate in the biosynthesis of isopentenyl pyrophosphate?

A)hydroxymethylglutaryl-CoA

B)mevalonylphosphate

C)acetoacetyl-CoA

D)dimethylallyl phosphate

E)mevalonic acid

Q4) Under anaerobic conditions in yeast cells, pyruvate is converted to acetaldehyde and ________, with the acetaldehyde being subsequently converted to ________ in a step that reoxidizes NADH to NAD+.

Q5) At biological pH, ATP has ________ negative charges per molecule.

A)4)0

B)3)3

C)2)8

D)1)1

E)0)6

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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids

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Q1) List the number of pairs of chromosomes in a human.

A)18 pairs of chromosomes

B)20 pairs of chromosomes

C)23 pairs of chromosomes

D)25 pairs of chromosomes

E)27 pairs of chromosomes

Q2) Draw the structure of dTTP.

Q3) Besides a possible difference in base structure, what is the major structural difference between ribo- and deoxyribonucleosides?

Q4) What are antigene and antisense agents?

Q5) How many billion base pairs are there in the total DNA of a human cell?

A)3

B)5

C)8

D)11

E)13

Q6) A commonly known nucleotide is adenosine 3', 5'-phosphate (cAMP). What is the structure of cAMP?

Q7) Draw the structure of ATP.

Q8) Draw the structure of guanosine.

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Chapter 27: Synthetic Polymers

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Q1) 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?

Q2) Which of the following statements concerning the stereochemistry of polymerization is (are)correct?

A)Polymers in the atactic configuration are more likely to be crystalline solids because regular packing of the polymer chains is easier.

B)Polymers in the isotactic configuration tend to be softer and more flexible than atactic polymers.

C)In general, radical polymerization leads primarily to branched polymers in the syndiotactic configuration.

D)The percentage of chains in the isotactic or syndiotactic configuration decreases as the polymerization temperature decreases.

E)none of the above

Q3) Provide the structure of poly(tetrafluoroethylene).

Q4) Draw the products which would result if poly(ethylene terephthalate)were hydrolyzed in hot aqueous NaOH.

Q5) Draw a short segment of plexiglass, using five monomers.

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Chapter 28: Pericyclic Reactions

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Q1) Which of the following reactions best describes the Diels-Alder reaction?

A)electrocyclic reaction

B)cycloaddition reaction

C)sigmatropic reaction

D)radical reaction

E)nucleophilic substitution reaction

Q2) Is the thermal [4+2] cycloaddition between allylanion and ethylene an allowed one? To answer, draw the HOMO of allyl anion and the LUMO of ethylene, and comment on the symmetry match of the two.

Q3) Under thermal conditions, (2E,4E)-hexadiene undergoes a ________ ring closure to yield ________.

A)conrotatory, cis-3,4-dimethylcyclobutene

B)conrotatory, trans-3,4-dimethylcyclobutene

C)disrotatory, cis-3,4-dimethylcyclobutene

D)disrotatory, trans-3,4-dimethylcyclobutene

Q4) Give a representation of the antibonding molecular orbital of the allyl anion.

Q5) Which molecular orbital is higher in energy: the in-phase or out-of-phase overlap of atomic orbitals?

Q6) Under thermal conditions, is an [8+2] cycloaddition suprafacial or antarafacial?

Q7) Explain what a node is and how it is formed.

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