Pharmaceutical Chemistry
Textbook Exam Questions
Course Introduction
Pharmaceutical Chemistry explores the design, synthesis, analysis, and development of chemical compounds used as medications. This course examines the principles of medicinal chemistry, including drug discovery, structure-activity relationships, pharmacokinetics, and pharmacodynamics. Students will learn about the roles of organic, inorganic, and analytical chemistry in the formulation, optimization, and quality control of pharmaceuticals, as well as the process of bringing a new drug from the lab to the market. The curriculum integrates knowledge of biochemistry, molecular biology, and toxicology to foster an understanding of how drugs interact with biological systems.
Recommended Textbook Organic Chemistry 3rd Edition by David R. Klein
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Chapter 1: A Review of General Chemistry: Electrons, Bonds, and
Molecular Properties
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Q1) The molecular geometry of carbon tetrachloride, CCl<sub>4</sub>, is _________ .
A) tetrahedral
B) trigonal planar
C) trigonal pyramidal
D) square planar
E) linear
Answer: A
Q2) The lone pair of electrons in the methyl anion, CH<sub>3</sub><sup>-</sup>, resides in which orbital?
A) s<sup>2</sup>
B) p
C) sp
D) sp<sup>3</sup>
E) sp<sup>2</sup>
Answer: D
Q3) Draw the Lewis structure for HCOOH and predict the hybridization state, molecular geometry and approximate bond angle around the central atom.
Answer: 11ea894b_ac4e_0c62_bba7_b5487186c235_TB4454_00_TB4454_00 sp<sup>2</sup>, trigonal planar, 120<sup>0</sup>
Page 3
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Chapter 2: Molecular Representations
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Q1) The spreading of positive or negative charge over two or more atoms in a compound is called_______.
A) isomerism
B) delocalization
C) stereoisomerism
D) localization
E) None of these
Answer: B
Q2) Draw a bond-line structure for each constitutional isomer with a molecular formula of C<sub>2</sub>H<sub>4</sub>O.
Answer: 11ea894b_ac5a_1aa7_bba7_01dafb0d203a_TB4454_00_TB4454_00
Q3) Draw significant resonance structures for N<sub>2</sub>O. Which of these is/are the most significant resonance structure(s)? Explain why.
Answer: 11ea894b_ac67_fced_bba7_874e270dd498_TB4454_00_TB4454_00
Resonance structure III is most significant, because the more electronegative oxygen atom carries a negative formal charge.
Q4) Draw the resonance hybrid of CH<sub>2</sub>CHCHCHCH<sub>2</sub><sup>+</sup>.
Answer: 11ea894b_ac68_7223_bba7_ffc309680577_TB4454_00_TB4454_00
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Chapter 3: Acids and Bases
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Q1) In a Brønsted-Lowry acid-base reaction, the reactants are _______.
A) Brønsted-Lowry acid and Brønsted-Lowry base
B) Brønsted-Lowry acid and conjugate base
C) Brønsted-Lowry base and conjugate acid
D) conjugate acid and conjugate base
E) Brønsted-Lowry acid and conjugate acid
Answer: A
Q2) As a result of the "leveling effect," the strongest acid that can exist in appreciable concentration in aqueous solution is ____.
A) H<sub>2</sub>SO<sub>4</sub>
B) HCl
C) H<sub>3</sub>O<sup>+</sup>
D) HNO<sub>3</sub>
E) All of these
Answer: C
Q3) Draw the conjugate base of CH<sub>3</sub>CH<sub>2</sub>NH<sub>2</sub>.
Answer: 11ea894b_ac6b_0a51_bba7_6bee57bb5622_TB4454_00_TB4454_00
Q4) Draw the conjugate acid of CH<sub>3</sub>OCH<sub>3</sub>
Answer: 11ea894b_ac6a_bc2d_bba7_b95ff4ea07c8_TB4454_00_TB4454_00
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Chapter 4: Alkanes and Cycloalkanes
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Q1) Draw a chair conformation of methylcyclohexane.
Q2) Draw an energy diagram for the conformational analysis of propane.
Q3) Of the following isomers of C<sub>9</sub>H<sub>20</sub>, which is the most stable?
A) nonane
B) 3-methyloctane
C) 2,2-dimethylheptane
D) 2,2,3,4-tetramethylpentane
Q4) What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol?
Q5) What is the structure of 3-ethyl-3-methylpentane?
Q6) What is the structure of an isopropyl group?
Q7) What is the structure of 1-cyclopropyl-3-methylcyclopentane?
Q8) Draw the lowest energy chair conformer of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.
Q9) Draw a chair conformation of cyclohexane showing all of the equatorial H's.
Q10) Draw the most stable conformation of trans-1,4-diethylcyclohexane.
Q11) What is the eclipsing cost of Br and H if the energy difference between the staggered and eclipsed conformations of bromoethane is 13 kJ/mol? Page 6
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Chapter 5: Stereoisomerism
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Q1) If a sample of carvone gives a specific rotation of 60 and the specific rotation of (R)-carvone is 61, does the unknown sample primarily have the R or S absolute configuration?
Q2) Draw the structure of the compound (S)-3-methylheptane.
Q3) What is the specific rotation of a sample of carvone that is an equal mixture of the R and S enantiomers? (R)- carvone has a specific rotation of 61.
A) 61
B) 64
C) 0
D) 61
Q4) What is the % ee of a sample of carvone that exhibits a specific rotation of 40, given that the specific rotation of (R)-carvone is 61?
Q5) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>6</sub>.
Q6) If a sample of carvone gives a specific rotation of 0 and the specific rotation of pure (R)-carvone is 61, what is the configuration of the unknown sample?
Q7) Draw the structure of the compound (R)-4-ethyloctane.
Q8) Stereoisomers that result from the hindered rotation of a single bond are called ___________.
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Chapter 6: Chemical Reactivity and Mechanisms
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Sample Questions
Q1) In a homolytic bond cleavage, ____ are formed.
A) ions
B) radicals
C) only cations
D) only anions
Q2) What is the effect of a catalyst on a reaction?
A) It increases the rate.
B) It decreases the entropy.
C) It changes the equilibrium.
D) It makes the products more stable.
Q3) Which of the following indicates a reaction with a positive G?
A) endergonic, spontaneous
B) endergonic, not spontaneous
C) exergonic, spontaneous
D) exergonic, not spontaneous
Q4) What is an intermediate?
A) A local maximum on the energy diagram.
B) A point on the reaction pathway that has a discrete minima.
C) A point half-way between the starting materials and products.
D) The highest energy compound on an energy diagram.
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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions
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Sample Questions
Q1) When drawing a curved arrow mechanism, the tail of the arrow starts at______.
A) the bond that is being formed
B) the atom with the positive charge
C) the source of electrons that is being moved
D) the location to which the electrons are being moved
Q2) Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.
Q3) Draw the E isomer of 2-methyl-3-heptene.
Q4) Which of the following is a weakest nucleophile in a polar protic solvent?
A) F<sup>-</sup>
B) Cl<sup>-</sup>
C) Br<sup>-</sup>
D) I<sup>-</sup>
E) All of these
Q5) Which of the following is a tertiary alkyl halide?
A) (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>Cl
B) (CH<sub>3</sub>)<sub>2</sub>CClCH<sub>2</sub>CH<sub>3</sub>
C) (CH<sub>3</sub>)<sub>2</sub>CHCHClCH<sub>3</sub>
D)
(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CHClCH<sub>2</sub>CH<sub>3</su
b>
Q6) Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more reactive Page 10
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Chapter 8: Addition Reactions of Alkenes
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Sample Questions
Q1) Addition reactions of alkenes are characterized by _________.
A) formation of a bond
B) addition of two groups across a double bond
C) breaking of a bond
D) A and B
E) B and C
Q2) What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H<sub>2</sub>?
A) 1-chloro-2-methylcyclohexane
B) 1-chloro-3-methylcyclohexane
C) 1-chloro-5-methylcyclohexane
D) 3-chloro-1-methylcyclohexane
E) None of the above
Q3) The alkene precursor to acetone is __________.
Q4) In an addition reaction to an alkene, the bond is ______.
A) a nucleophile
B) an electrophile
C) a leaving group
D) A and B
E) B and C
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Chapter 9: Alkynes
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Q1) Provide the IUPAC name for Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>C CH.
A) 6,6,6-trichloro-1-hexyne
B) 1,1,1-trichloro-5-hexyne
C) 5,5,5-trichloro-1-pentyne
D) 1-heptyne
E) trichlorobutylacetylene
Q2) Identify the product of the reaction of an alkyne with sodium and ammonia.
A) cis alkene
B) trans alkene
C) diene
D) alkyne
E) alkane
Q3) Select the best reagent expected to convert 3-heptyne to cis-3-heptene.
A) NaNH<sub>2</sub>, NH<sub>3</sub>
B) Na, NH<sub>3</sub>
C) H<sub>2</sub>, Lindlar's catalyst
D) Both A and C
E) Both B and C
Q4) What reagent(s) are required to prepare trans-2-heptene from 2-heptyne?
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Chapter 10: Radical Reactions
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Sample Questions
Q1) Propose a synthesis of 2-methylpropene from 2-methylpropane.
Q2) Propose a synthesis of 2-butyn-1-ol from propane.
Q3) Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.
Q4) Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methylbenzene produces exactly three monobrominated compounds (including stereoisomers). Draw the products of this reaction.
Q5) Draw all possible monochlorination products of 3,3-dimethylpentane, including stereoisomers.
Q6) Which monomer is used for the synthesis of poly(vinyl chloride)?
A) 1-chloroethene
B) 1-chloroethane
C) 1,2-dichloroethene
D) 1-chloro-1-propene
Q7) A bromine radical can add to the bond of 2-methylpropene. Give the arrows to show this process and the expected result.
Q8) Propose a synthesis of polyethylene from ethane.
Page 14
Q9) Propose a synthesis of 4-penten-2-ol from propene.
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Chapter 11: Synthesis
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Sample Questions
Q1) Taxol is found in the ______ tree
A)tea
B)Eucalyptus
C)sausage fruit
D)Baobab
E)Pacific yew
Q2) Devise a synthetic route to convert 5-methyl-1-hexene into 5-methylhexanal.
Q3) Reaction of compound A (molecular formula = C<sub>7</sub>H<sub>12</sub>) with sodium amide, followed by reaction with 1-bromobutane produces a compound with a structure of (CH<sub>3</sub>)<sub>2</sub>CHCH(CH<sub>3</sub>)CC(CH<sub>2</sub>)<sub>3</s ub>CH<sub>3</sub>. What is the name of compound A?
A) 2,3-dimethylnon-4-yne
B) 2,2-dimethylpent-1-yne
C) 3,4-dimethylpent-1-yne
D) 4,4-dimethylhept-1-yne
E) 1-heptyne
Q4) Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).
Q5) Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.
Q6) Devise a synthetic route to prepare 1,3-dibromopropan-2-ol from propene.
Q7) Propose a synthesis of 1-butene from propyne.
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Chapter 12: Alcohols and Phenols
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Sample Questions
Q1) Identify rubbing alcohol.
A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol
Q2) Identify the alcohol in alcoholic drinks.
A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol
Q3) Identify the type of bonding between molecules of alcohol.
A) ion-ion
B) van der Waals forces
C) hydrogen bonding
D) ion-dipole
E) London dispersion
Q4) Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.
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Chapter 13: Ethers and Epoxides; Thiols and Sulfides
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Sample Questions
Q1) Provide the structure for tetrahydrofuran.
Q2) Draw all constitutional isomers with molecular formula C<sub>6</sub>H<sub>14</sub>O having an ether functional group and provide the IUPAC name for each isomer.
Q3) Which of the following crown ether solvates sodium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these
Q4) Identify the conditions of oxymercuration-demercuration.
A) anti-Markovnikov, rearrangement possible
B) anti-Markovnikov, no rearrangement possible
C) Markovnikov, rearrangement possible
D) Markovnikov, no rearrangement possible
Q5) Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.
Q6) Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene.
Q7) The polyethers that function like crown ethers are called _________.
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Q8) Can you prepare diisopropyl ether as the major product by heating 2-propanol in the presence of sulfuric acid? Explain your answer.
Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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Q1) Which of the following is currently most often used to indicate the location of a signal on an IR spectrum?
A) wavelength
B) wavenumber
C) frequency
D) A and B
E) all of these
Q2) Provide a molecular formula that is consistent with the following mass spectral data. M<sup>+</sup> <sup> </sup>at m/z = 136, relative height = 65.6% (M+1)<sup>+</sup> <sup> </sup>at m/z = 137, relative height = 6.2%
Q3) Provide a molecular formula that is consistent with the following mass spectral data. M<sup>+</sup> <sup> </sup>at m/z = 73, relative height = 86.1% (M+1)<sup>+</sup> <sup> </sup>at m/z = 74, relative height = 3.2%
Q4) A compound with molecular formula C<sub>6</sub>H<sub>10</sub>O, shows absorptions at 1720 cm<sup>-1</sup> and at 2980 cm<sup>-1</sup> on the IR spectrum. Propose a possible structure for this compound.
Q5) Warmer objects emit more __________ radiation.
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Chapter 15: Nuclear Magnetic Resonance Spectroscopy
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Q1) Propose a structure for a compound, with molecular formula C<sub>8</sub>H<sub>19</sub>N, that fits the following spectroscopic data: IR: 3400 cm<sup>-1</sup> <sup>1</sup>H NMR: 0.9 \(\delta\) (triplet, 6H), 1.1 \(\delta\) (singlet, 1H, exchanges with D<sub>2</sub>O), 1.3 \(\delta\) (sextet, 4H), 1.4 \(\delta\) (quintet, 4H), 2.6 \(\delta\) (triplet, 4H) <sup>13</sup>C NMR: 13.7, 20.5, 30.4, 49.2
Q2) Identify the splitting pattern for a CH<sub>3</sub> in an off-resonance decoupled <sup>13</sup>C NMR spectrum.
A) no peak
B) singlet
C) doublet
D) triplet
E) quartet
Q3) In an NMR spectrometer, the receiver coil records a complex signal, called a ________________, which is converted into a spectrum via a mathematical technique called a ____________________.
Q4) List the most common nuclei that are used in NMR.
Q5) NMR is an abbreviation for ____________ ____________ __________.
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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
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Q1) Identify the MOs that react to form cyclohexene via a Diels-Alder Reaction.
A) LUMO of 1,3-butadiene and HOMO of ethylene
B) LUMO of 1,3-butadiene and LUMO of ethylene
C) HOMO of 1,3-butadiene and HOMO of ethylene
D) HOMO of 1,3-butadiene and LUMO of ethylene
Q2) Identify the conjugated diene(s).
A. 4-methyl-1,3-heptadiene
B. 3-methyl-1,5-heptadiene
C. 2-methyl-2,4-heptadiene
D. 4-methyl-1,4-heptadiene
E. 5-methyl-2,3-heptadiene
Q3) The polymerization of isoprene to produce synthetic rubber is a special case of ____- addition.
Q4) Which of the following compounds has the longest \(\lambda\)<sub>max</sub>?
A) (E )-2-pentene
B) (Z)-2-pentene
C) 1-pentene
D) 1,3-hexadiene
E) 1,3,5-hexatriene
Q5) Provide the structure for (E)-1,3-pentadiene.
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Chapter 17: Aromatic Compounds
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Q1) What is the main difference between an aromatic and antiaromatic compound?
A) Aromatic compounds must be cyclic and planar, but not antiaromatic compounds
B) Aromatic compounds must be monocyclic.
C) Antiaromatic compounds must have a conjugated system with a p orbital at every vertex
D) Aromatic compounds must satisfy Hückel's rule.
E) none of these
Q2) Which of the following describes the current view of the two Kekulé structures for benzene?
A) they are both correct structures for benzene
B) the two structures are in equilibrium
C) the two structures adequately describe benzene
D) benzene is a resonance hybrid of the two structures
E) None of the above
Q3) For a compound to be aromatic, it must have a planar cyclic conjugated \(\pi\) system along with an _____ number of electron pairs.
A) even
B) odd
C) either even or odd
D) none of these
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Chapter 18: Aromatic Substitution Reactions
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Q1) Identify the electrophile in the nitration of benzene.
A) sulfonium ion
B) nitrogen dioxide
C) nitronium ion
D) nitrous oxide
E) Nitrogen dioxide
Q2) Which of the following compounds will not undergo nucleophilic aromatic substitution?
A) 1-chloro-2,4-dinitrobenzene
B) 1-bromo-4-nitrobenzene
C) o-chloronitrobenzene
D) m-chloronitrobenzene
E) p-chloronitrobenzene
Q3) Identify the product from the reaction of nitrobenzene with iron and hydrochloric acid, followed with base.
A) nitrobenzene
B) benzene
C) aniline
D) 1,3-dinitrobenzene
E) 1,4-dinitrobenzene
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Chapter 19: Aldehydes and Ketones
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Q1) Provide the structure for benzophenone.
Q2) Suggest a stepwise synthesis for 4-methyl-1-pentanamine from 3-methyl-1-butanol.
Q3) Name the aldehyde or ketone that is used as a preservative.
A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether
Q4) Name the aldehyde or ketone that is found in nail polish remover.
A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether
Q5) Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.
Q6) Suggest a stepwise synthesis for 3-phenylpropanal from benzyl alcohol.
Q7) Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.
Page 23
Q8) Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
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Chapter 20: Carboxylic Acids and Their Derivatives
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Q1) Provide the reagents necessary to convert 4,5-dimethyl-1-hexanol into N-cyclopentyl-4,5-dimethylhexanamide.
Q2) Give the IUPAC name for malonic acid.
A) ethanedioic acid
B) propanedioic acid
C) butanedioic acid
D) pentanedioic acid
E) benzoic acid
Q3) Provide the structure for cyclopentanecarbonyl chloride.
Q4) Which one of the following compounds has the highest boiling point?
A) butanoic acid
B) 1-butanol
C) 2-butanone
D) methoxyethane
E) butanal
Q5) Propose a stepwise synthesis for 2-phenylethanoyl chloride, using toluene and/or carbon dioxide as your only source of carbon and any other reagents necessary.
Q6) Provide the structure for acetic formic anhydride.
Q7) Ethanoic acid is commonly known as ________.
Page 25
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Chapter 21: Alpha Carbon Chemistry: Enols and Enolates
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Q1) Provide the reagents necessary to convert acetophenone to benzoic acid.
A) PCC/CH<sub>2</sub>Cl<sub>2</sub>
B) 1. NaOH/Br<sub>2</sub>
2) H<sub>3</sub>O<sup>+</sup>
C) 1. KMnO<sub>4</sub>/NaOH/H<sub>2</sub>O
2) H<sub>3</sub>O<sup>+</sup>
D) 1. Br<sub>2</sub>/PBr<sub>3</sub>
2) H<sub>2</sub>O
E) both B and C
Q2) Which of the following bases will completely convert 1,4-cyclohexanedione into an enolate?
A) sodium hydroxide
B) sodium ethoxide
C) LDA
D) sodium hydride
E) both C and D
Q3) Provide the structure of the enolate when acetophenone is treated with a strong base.
Q4) Explain why CH<sub>3</sub>ONa should not be used for Claisen condensation of ethylbutanoate.
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Chapter 22: Amines
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Q1) What is the structure for N-ethylbenzylamine?
Q2) What is the structure for 1-butanamine?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> B)
CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> C)
(CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NCH<sub>2</sub>CH(CH<sub>3</sub> )<sub>2</sub>
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>4</sub>N<sup>+ </sup>OH<sup>-</sup>
E) (CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub>
Q3) Which of the following is a secondary amine?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> B)
CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> C)
(CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NCH<sub>2</sub>CH(CH<sub>3</sub> )<sub>2</sub>
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>4</sub>N<sup>+ </sup>OH<sup>-</sup>
E) (CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub>
Q4) Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C followed by o-ethylphenol? 2
Q5) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis. Page 27
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Chapter 23: Introduction to Organometallic Compounds
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Sample Questions
Q1) Which of the following solvents is/are good solvents to be used in the preparation of organometallic reagents such as organolithiums and Grignard reagents? Select all that apply.
A) ethanol
B) diethyl ether
C) cyclohexanol
D) tetrahydrofuran
E) dioxane
Q2) Which of the following functional groups does not afford an alcohol when treated with a Grignard reagent followed by a protic work-up.
A) ketone
B) aldehyde
C) ester
D) epoxide
E) nitrile
Q3) Which of the following compounds has the least nucleophilic carbon atom?
A) CH<sub>3</sub>CH<sub>2</sub>MgBr
B) CH<sub>3</sub>CH<sub>2</sub>MgI
C) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>Zn
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>Cu
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Chapter 24: Carbohydrates
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Sample Questions
Q1) Which one of the following heterocyclic amines is not a base in RNA?
A) uracil
B) thymine
C) cytosine
D) adenine
E) guanine
Q2) Identify the classification for D-galactose.
A) aldotetrose
B) ketotetrose
C) aldopentose
D) ketopentose
E) aldohexose
Q3) The general structure of carbohydrates are _______.
A) polyhydroxy esters
B) polyhydroxy aldehydes
C) polyhydroxy ketones
D) polyhydroxy alkanes
E) B and C
Q4) Draw the Fisher projection for D-galactose.
Q5) Draw the Haworth projection for \(\beta\)-D-erythrofuranose.
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Chapter 25: Amino Acids, Peptides, and Proteins
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Sample Questions
Q1) Provide the steps necessary to prepare the tetrapeptide Thr-Val-Ile-Met using the Merrifield synthesis.
Q2) The ______ structure of a protein is most important because the ______of the amino acids determines its overall shape, function and properties.
A) primary, twisting
B) primary, sequence
C) secondary, twisting
D) secondary, folding
E) tertiary, folding
Q3) Which of the following dipeptides is formed when tyrosine is treated with (BoC)<sub>2</sub>O and proline is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?
A) Tyr-Pro
B) Pro-Tyr
C) Pro-Pro
D) Tyr-Tyr
E) all of these
Q4) How do enzymes speed up a reaction?
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Chapter 26: Lipids
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Sample Questions
Q1) Which one of the following is a class of complex lipids?
A) steroids
B) terpenes
C) waxes
D) prostaglandins
E) furans
Q2) A triglyceride produced a linoleic acid residue, a palmitoleic acid residue and an oleic acid residue, when heated in the presence of an acid. Provide one of the possible structures for this triglyceride.
Q3) Which of the following is a common characteristic of prostaglandins PGA, PGB and PGC?
Q4) Explain why fatty acids cannot form a bilayer.
Q5) Aspirin blocks the biosynthesis of which of the following eicosanoids?
A) leukotrienes
B) prostaglandins
C) thromboxanes
D) prostacyclins
E) C and D
Q6) Which of the following is a common characteristic of prostaglandins PGD and PGE?
Q7) Why is decanol more efficient at crossing the cell membrane than hexanol?
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Chapter 27: Synthetic Polymers
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Sample Questions
Q1) Which of the following is used as an initiator in radical polymerization?
A) BF<sub>3</sub>, H<sub>2</sub>O
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Li
C) ROOR
D) NaOH
E) H<sub>2</sub>O
Q2) Provide the structure of a region of an alternating copolymer constructed from propylene and acrylonitrile.
Q3) Identify the polymer used in plumbing.
A) polytetrafluoroethylene
B) polystyrene
C) polypropylene
D) polyethylene
E) poly(vinyl chloride)
Q4) Which of the following functional groups are common in biodegradable polymers?
A) esters
B) amides
C) anhydrides
D) A and B
E) A and C
Page 33
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