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Structure and Reactivity in Organic Chemistry
Midterm Exam
Course Introduction
This course explores the fundamental principles governing the structures and reactivity patterns of organic molecules. Topics include electronic structure, bonding, stereochemistry, and the physical properties of organic compounds. Students will examine mechanisms of key organic reactions such as nucleophilic substitution, elimination, and addition, and learn how these processes are influenced by molecular structure and reaction conditions. By analyzing reaction intermediates and transition states, the course provides insight into the predictive tools used to understand and control organic transformations, preparing students for advanced topics in organic synthesis and chemical biology.
Recommended Textbook
Organic Chemistry 3rd Edition by David R. Klein
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27 Chapters
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Page 2
Chapter 1: A Review of General Chemistry: Electrons, Bonds, and
Molecular Properties
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Sample Questions
Q1) Which of the following compounds has polar covalent bonds?
A) NH<sub>3</sub>
B) Na<sub>2</sub>O
C) H<sub>2</sub>
D) KF
E) Both A and C
Answer: A
Q2) Which of the following covalent bonds has the largest dipole moment?
A) C-C
B) C-H
C) C-O
D) N-H
E) H-F
Answer: E
Q3) Draw the Lewis structure for NH<sub>2</sub>CN including formal charges, if any?
Answer: 11ea894b_ac3f_17fd_bba7_bb70517ce0dc_TB4454_00_TB4454_00
Q4) Draw the Lewis structure for ozone, O<sub>3</sub><sub>,</sub> including formal charges, if any?
Answer: 11ea894b_ac3f_661f_bba7_014dd8e54436_TB4454_00_TB4454_00
Page 3
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Chapter 2: Molecular Representations
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Sample Questions
Q1) Draw the Lewis structure for (CH<sub>3</sub>)<sub>3</sub>C(CH<sub>2</sub>)<sub>2</sub>OCH(CH<sub>2</sub> CH<sub>3</sub>)<sub>2</sub>.
Answer: 11ea894b_ac55_d4ca_bba7_bfadc8d364ce_TB4454_00_TB4454_00
Q2) Draw the Lewis structure for CH<sub>3</sub>C C(CH<sub>2</sub>)<sub>3</sub>C(CH<sub>3</sub>)<sub>3</sub>.
Answer: 11ea894b_ac55_adb9_bba7_b731aff568d8_TB4454_00_TB4454_00
Q3) Draw two resonance structures for HN<sub>3</sub>.
Answer: 11ea894b_ac66_eb6c_bba7_4f79b39b0027_TB4454_00_TB4454_00
Q4) Draw a bond-line structure for CH<sub>3</sub>C C(CH<sub>2</sub>)<sub>3</sub>C(CH<sub>3</sub>)<sub>2</sub>C H<sub>2</sub>OCH<sub>3</sub>.
Answer: 11ea894b_ac59_f396_bba7_81bf1cc783ac_TB4454_00_TB4454_00
Q5) Draw a bond-line structure for each constitutional isomer with molecular formula C<sub>4</sub>H<sub>10</sub>O.
Answer: 11ea894b_ac5a_8fdb_bba7_8bcc5aebc515_TB4454_00_TB4454_00 11ea894b_ac5a_8fdc_bba7_e3d8190b09e5_TB4454_00_TB4454_00
Q6) 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
Page 4
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Chapter 3: Acids and Bases
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Sample Questions
Q1) Identify a conjugate acid.
A) proton acceptor
B) proton donor
C) species remaining after acid is deprotonated
D) species remaining after base is protonated
Answer: D
Q2) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3,</sub> is best classified as a ____.
A) Brønsted-Lowry acid
B) Lewis acid
C) Brønsted-Lowry base
D) Lewis base
E) Both C & D
Answer: E
Q3) Identify the most sterically hindered alcohol.
A) CH<sub>3</sub>OH
B) CH<sub>3</sub>CH<sub>2</sub>OH
C) (CH<sub>3</sub>)<sub>2</sub>CHOH
D) (CH<sub>3</sub>)<sub>3</sub>COH
Answer: D
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Chapter 4: Alkanes and Cycloalkanes
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Sample Questions
Q1) The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.
A) hydrogenation
B) cracking
C) reforming
D) hydrolysis
Q2) Draw the most stable conformation of trans-1,4-diethylcyclohexane.
Q3) Draw a chair conformation of methylcyclohexane.
Q4) Draw the most stable chair conformer of the most stable isomer of 1,3,5-trimethylcyclohexane.
Q5) Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.
Q6) 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
Q7) Draw a chair conformation of cyclohexane showing all of the equatorial H's.
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Q8) Draw the lowest energy chair conformer of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.
Chapter 5: Stereoisomerism
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Sample Questions
Q1) What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is 61?
A) 26%
B) 51%
C) 49%
D) 75%
Q2) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>8</sub>.
Q3) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -F II. -H III. -OH IV. -SH
Q4) When a racemic mixture is reacted with a single enantiomer of another compound, then a pair of _________ is formed.
A) identical compounds
B) enantiomers
C) diastereomers
D) none of the above
Q5) Draw the structure of the compound (S)-3-methylheptane.
Q6) Draw all possible stereoisomers of 1,3,5-trimethylcyclohexane.
Q7) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>6</sub>.
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Chapter 6: Chemical Reactivity and Mechanisms
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Sample Questions
Q1) 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
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) In a heterolytic bond cleavage, ____ are formed.
A) ions
B) radicals
C) only cations
D) only anions
Q4) Does a reaction with a H of 14 kJ/mol and a S of 150 J/mol·K at 298 K favor reactants or products?
Q5) Draw an energy diagram for a concerted exothermic reaction.
Q6) Does a reaction with a value of 0 for G favor reactants or products?
Q7) Draw an energy diagram for an endothermic reaction with two steps.
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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 head of the arrow goes to__________.
A) the bond that is being formed
B) the bond that is being broken
C) the source of electrons that is being moved
D) the location to which the electrons are being moved
Q2) 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>
Q3) Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more reactive in an E2 elimination.
Q4) Identify the methylating agent used in biological systems.
A) methyl iodide
B) S-adenosylmethionine
C) methylalanine
D) methylproline
E) methyl bromide
Q5) Provide the structure for 1-chloro-4-isopropylheptane. Page 9
Q6) Provide the structure for cis-1,2-dibromocyclopentane.
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Chapter 8: Addition Reactions of Alkenes
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Sample Questions
Q1) What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H<sub>2</sub>?
A) No reaction
B) cis-1,2-dimethylcyclohexane
C) trans-3,4-dimethylhexane
D) trans-1,2-dimethylhexane
E) None of the above
Q2) Draw Fischer projections of the major product of the reaction between (Z)?2?methyl-3-hexene and aqueous Br<sub>2</sub>.
Q3) What is a compound that does not have a double bond?
A) allicin (garlic)
B) geraniol (roses)
C) cholesterol
D) limonene (oranges)
E) ammonia
Q4) The alkene precursor to ethanol is __________.
Q5) A reaction that could potentially yield two or more constitutional isomers, but as in hydroboration-oxidation produces only one isomer, is said to be
Page 11
Q6) The alkene precursor to acetone is __________.
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Chapter 9: Alkynes
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Sample Questions
Q1) Describe the shape for acetylene.
Q2) What are the products of the reaction shown below? CH<sub>3</sub>OH + CH<sub>3</sub>C C<sup>-</sup>Na<sup>+</sup> ?
A) CH<sub>3</sub>C CCH<sub>3</sub> + Na<sup>+</sup>OH<sup>-</sup>
B) CH<sub>3</sub>C CH + CH<sub>3</sub>O<sup>-</sup>Na<sup>+</sup>
C) CH<sub>3</sub>C COCH<sub>3</sub> + Na<sup>+</sup>OH<sup>-</sup>
D) CH<sub>3</sub>OC CH + Na<sup>+</sup>CH<sub>3</sub><sup>-</sup>
E) no reaction
Q3) Provide the IUPAC name for CH<sub>3</sub>C CC(CH<sub>3</sub>)<sub>2</sub>CH(CH<sub>2</sub>CH<sub>3</su b>)<sub>2</sub>.
Q4) Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.
A) cis-3-hexene
B) trans-2-hexene
C) 3-hexyne
D) 2-hexyne
E) cis-2-hexene
Q5) Provide the IUPAC name for CH<sub>3</sub>CHBrC C(CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>.
Page 12
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Chapter 10: Radical Reactions
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Sample Questions
Q1) Draw the arrows to show the propagation steps in the chlorination of propane to produce 2-chloropropane.
Q2) Both compounds A and B have molecular formula C<sub>6</sub>H<sub>14</sub>.
Monochlorination of compound A results in the formation of two constitutional isomers. Monochlorination of compound B results in the formation of four constitutional isomers. Identify compounds A and B, and show the products of each monochlorination.
Q3) A bromine radical can add to the bond of 2-methylpropene. Give the arrows to show this process and the expected result.
Q4) Compound A has molecular formula C<sub>6</sub>H<sub>12</sub>. Upon treatment with NBS and irradiation with UV light, exactly two compounds (including stereoisomers), are formed. Suggest a possible structure for compoundA.
Q5) Cyclic compound A has molecular formula C<sub>5</sub>H<sub>10</sub> and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.
Q6) Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.
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Chapter 11: Synthesis
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Sample Questions
Q1) 2-Methylpentane (C<sub>6</sub>H<sub>14</sub>) can be converted, through a multistep synthesis, to a compound with a molecular formula of C<sub>6</sub>H<sub>13</sub>Br that shows exactly six resonances in its proton-decoupled <sup>13</sup>C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.
Q2) Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.
A) hept-1-en-4-yne
B) hept-6-en-3-yne
C) hept-3-en-6-yne
D) hept-4-en-1-yne
E) hept-2-en-4-yne
Q3) What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?
A) 1
B) 2
C) 3
D) 4
E) 5
Q4) Devise a synthetic route to prepare 3-bromo-1-propanol from propene.
Page 14
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Chapter 12: Alcohols and Phenols
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Sample Questions
Q1) The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene goes via a(n) _____.
A) S<sub>N</sub>1 mechanism
B) S<sub>N</sub>2 mechanism
C) E1 mechanism
D) E2 mechanism
E) None of these.
Q2) Identify the characteristics of the oxymercuration-demercuration of an alkene.
A) Markovnikov, with rearrangement possible
B) Markovnikov, with no rearrangement possible
C) anti-Markovnikov, with rearrangement possible
D) anti-Markovnikov, with no rearrangement possible
Q3) Explain why cyclohexanol has a pK<sub>a</sub> of 18 and phenol has a pK<sub>a</sub> of 10. Use structural drawings to explain your reasoning.
Q4) Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..
Q5) Nature's catalysts are called ________.
Q6) Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol.
Q7) Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.
Q8) Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
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Chapter 13: Ethers and Epoxides; Thiols and Sulfides
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Sample Questions
Q1) Which of the following crown ether solvates lithium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these
Q2) Provide the structure for oxetane.
Q3) What is the common name for (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OCH(CH<sub>3</sub>)<sub>2</sub >?
A) diisobutyl ether
B) isobutyl isopropyl ether
C) sec-butyl isopropyl ether
D) diisopropyl ether
E) none of these
Q4) What type of molecular interactions do ethers have?
A) dipole-dipole interactions
B) ion-dipole interactions
C) ion-ion interactions
D) London dispersion forces
E) hydrogen bonding
Page 16
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Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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Sample Questions
Q1) Calculate the degree of unsaturation for C<sub>5</sub>H<sub>5</sub>Br<sub>2</sub>NO.
A) 4
B) 6
C) 2
D) 3
E) 7
Q2) Provide the structure of the major fragment that results when the molecular ion of (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> undergoes fragmentation.
Q3) Which of the following bonds has the strongest absorption?
A) C=N
B) C C
C) C=O
D) sp<sup>2</sup> C-H
E) C-O
Q4) Provide a molecular formula that is consistent with the following mass spectral data. M<sup>+</sup> <sup> </sup>at m/z = 167, relative height = 50.0% (M+1)<sup>+</sup> <sup> </sup>at m/z = 168, relative height = 4.4%
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Chapter 15: Nuclear Magnetic Resonance Spectroscopy
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Sample Questions
Q1) How many signals would you expect in the <sup>1</sup>H NMR spectrum of (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>?
A) 1
B) 2
C) 3
D) 4
E) 5
Q2) The coupling constant (J) for bromoethane is 7 Hz when the <sup>1</sup>H NMR spectrum is acquired at 250 MHz. What is the coupling constant between these protons when the spectrum is acquired at 500 MHz?
A) 3.5 Hz
B) 7 Hz
C) 14 Hz
D) 21 Hz
E) 1 Hz
Q3) Draw a structure, with a formula of C<sub>5</sub>H<sub>13</sub>N, which has an integration of 9H, 3H, 1H.
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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Sample Questions
Q1) Identify the pericyclic reaction in which no sigma bonds are formed and no pi bonds are broken.
A) sigmatropic rearrangement
B) cycloaddition reaction
C) electrolytic reaction
D) this is not a pericyclic reaction
Q2) Identify the color of a compound that absorbs blue light.
A) orange
B) green
C) red
D) blue
E) yellow
Q3) How many electrons does the HOMO of 1,3-pentadiene have in its excited state?
A) 1
B) 2
C) 3
D) 4
E) none
Q4) The reaction of 1,3-butadiene with hydrogen halide at 40°C will undergo _____ -addition under ____________ control.
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Chapter 17: Aromatic Compounds
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Sample Questions
Q1) Identify the number of \(\pi\) electrons present in an aromatic compound.
A) 4n + 2
B) 2n + 2
C) 4n
D) 2n
E) 3n
Q2) Provide the reagent(s) necessary to convert toluene to benzoic acid.
A)
Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>/H<sub>2</sub>SO<sub>4</sub>/H<sub >2</sub>O
B) 1. NBS, \(\Delta\) 2.NaOH
C) 1. LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup>
D) H<sub>2</sub>, Pd
E) 1. CO<sub>2,</sub> 2. H<sub>3</sub>O<sup>+</sup>
Q3) Molecular orbitals of equal energy are referred to as _________ orbitals.
Q4) Provide a structure for the compound with molecular formula C<sub>9</sub>H<sub>9</sub>ClO and with the following spectroscopic data.
IR: 1680 cm<sup> 1</sup>
<sup>1</sup>H NMR: 3.5 \(\delta\) (triplet, 2H), 4.0 \(\delta\) (triplet, 2H), 7.4 \(\delta\) (triplet, 2H), 7.6 \(\delta\) (triplet, 1H), 7.9 \(\delta\) (doublet, 2H)
Page 20
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Chapter 18: Aromatic Substitution Reactions
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Sample Questions
Q1) Which one of the following substituents will not direct the incoming group to the meta position during electrophilic aromatic substitution?
A) -NO<sub>2</sub>
B) -C\(\equiv\)N
C) -OCH<sub>3</sub>
D) -COOH
E) all of these
Q2) Provide a stepwise curved arrow mechanism for the chlorination of benzene in the presence of FeCl<sub>3</sub>.
Q3) Give the preferred products from the nitration of bromobenzene.
Q4) Which of the following substituents will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?
A) -CH<sub>2</sub>CH<sub>3</sub>
B) -CF<sub>3</sub>
C) -OCH<sub>3</sub>
D) -COOCH<sub>3</sub>
E) both A and C
Q5) A halogen ___________ the benzene ring; the ring is __________ reactive than benzene.
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Chapter 19: Aldehydes and Ketones
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Q1) The <sup>1</sup>H NMR spectrum of a compound with formula C<sub>7</sub>H<sub>14</sub>O shows only two signals. Which one of the following is a possible structure for this compound?
A) 2-heptanone
B) 3-heptanone
C) 2,4-dimethyl-3-pentanone
D) 2,2-dimethyl-3-pentanone
E) Two of the above
Q2) Provide the structure for benzophenone.
Q3) Provide the structure for m-nitroacetophenone.
Q4) Provide the structure for (S)-3-chlorocyclohexanone.
Q5) Name the aldehyde or ketone that is used as a preservative.
A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether
Q6) Benzaldehyde is less reactive than ethanal towards nucleophilic addition reactions. Explain why using words as well as structural drawings.
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Q7) Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
Chapter 20: Carboxylic Acids and Their Derivatives
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Q1) Ethanoic acid is commonly known as ________.
Q2) Give the IUPAC name for glutaric acid.
A) ethanedioic acid
B) propanedioic acid
C) butanedioic acid
D) pentanedioic acid
E) benzoic acid
Q3) 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.
Q4) A compound with molecular formula C<sub>9</sub>H<sub>10</sub>O<sub>2</sub> exhibits a triplet at \(\delta\) 1.2 (3H), a quartet at \(\delta\) 2.6 (2H), a doublet at \(\delta\) 7.3 (2H), a doublet at \(\delta\) 8.0 (2H) and a singlet at \(\delta\) 11 (1H) in its <sup>1</sup>H NMR spectrum. What is the structure for this compound?
Q5) Propose a stepwise synthesis for N-propylbutanamide, using 1-proanol and/or carbon dioxide as your only source of carbon and any other reagents necessary.
Q6) Provide the structure for 5-chloro-3-isopropyloctanoic acid.
Q7) Provide the structure for benzoyl chloride.
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Chapter 21: Alpha Carbon Chemistry: Enols and Enolates
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Q1) An intermolecular Claisen condensation is called a _____________.
Q2) Which one of the following compounds is most acidic?
A) ethyl acetoacetate
B) 2-butanone
C) ethyl pentanoate
D) 1-butanol
E) 3-pentanone
Q3) Which of the following ketones will give a positive haloform test?
A) 3-heptanone
B) 3-hexanone
C) cyclohexanone
D) 2-pentanone
E) 2-methyl-3-hexanone
Q4) Provide the structure of the enolate when acetophenone is treated with a strong base.
Q5) Provide the structure of the enol when 3,3,6-trimethyl-4-heptanone is treated with acid.
Q6) Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.
Q7) Give the organic by-product in a haloform reaction.
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Chapter 22: Amines
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Sample Questions
Q1) 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>
Q2) Which of the following is a tertiary 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>
Q3) What is the structure for 3-chloro-N-ethyl-1-pentanamine?
Q4) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.
Q5) What is the structure for N-ethylbenzylamine?
Q6) The ________ reaction is used to prepare primary amines by using potassium Page 25
phthalimide. This reaction proceeds by a ________ mechanism.
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Chapter 23: Introduction to Organometallic Compounds
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Sample Questions
Q1) Identify the product when an ester reacts with two equivalents of a Grignard reagent.
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) carboxylic acid
E) ketone
Q2) Identify the product when formaldehyde reacts with one equivalent of a Grignard reagent.
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) carboxylic acid
E) ketone
Q3) What functional group most typically results when a Grignard Reagent reacts with an acid halide, after aqueous workup?
Q4) The Heck reaction requires the presence of a base.
A)True
B)False
Q5) Each intermediate in alkene metathesis is formed by _____ cycloaddition
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Chapter 24: Carbohydrates
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Sample Questions
Q1) Identify the monomer in cellulose.
A) (\(\alpha\)-D-glucose)
B) (\(\beta\)-D-glucose)
C) (\(\alpha\)-D-galactose)
D) (\(\beta\)-D-fructose)
E) maltose
Q2) When D-erythrose is treated with NaBH<sub>4</sub>/H<sub>2</sub>O, it forms
A) a racemic mixture of alditols
B) a meso alditol
C) an optically active alditol
D) an optically active aldonic acid
E) none of these
Q3) A polysaccharide found in the exoskeletons of insects and arthropods is called _______.
Q4) The sequence of reactions that results in a chain lengthening of the aldose chain is called the _______________ synthesis.
Q5) Predict the product(s) when cellobiose is treated with excess acetic anhydride/pyridine.
Page 28
Q6) Identify the most common naturally occurring ketose.
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Chapter 25: Amino Acids, Peptides, and Proteins
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Sample Questions
Q1) Which of the following tetrapeptides is not cleaved by chymotrypsin?
A) Gly-Lys-Cys-Trp
B) Cys-Tyr-Arg-Phe
C) Phe-Ser-Ile-Lys
D) Ala-Trp-Tyr-Arg
E) Phe-Met-Pro-Arg
Q2) In \(\alpha\)-amino acids the amino and carboxylic acid groups are separated by ____,
A) two carbon atoms
B) one carbon atom
C) peptide linkage
D) amide linkage
E) none of these
Q3) Which one of the following amino acids contain a sulfur atom?
A) cysteine
B) serine
C) glutamine
D) leucine
E) proline
Q4) Provide the structure of the predominant form of valine at pH 10?
Page 29
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Chapter 26: Lipids
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Sample Questions
Q1) Predict the product when testosterone is treated with PCC.
Q2) Which of the following is(are) synthesized from arachidonic acid?
A) leukotrienes
B) prostaglandins
C) thromboxanes
D) prostacyclins
E) all of these
Q3) The reaction of triglycerides with a base is a(n) ________ reaction.
A) esterification
B) transesterification
C) saponification
D) autooxidation
E) oxidation
Q4) Explain why fatty acids cannot form a bilayer.
Q5) Which of the following is an anabolic steroid?
A) cortisone
B) androsterone
C) esrone
D) nandrolone
E) progesterone
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Chapter 27: Synthetic Polymers
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Sample Questions
Q1) _________ polymerization usually forms living polymers if the process is not terminated by an electrophile.
A) anionic
B) cationic
C) radical
D) condensation
E) elimination
Q2) An isotactic polymer has a _______ configuration.
A) random
B) alternating
C) same
D) block
E) graft
Q3) 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
Q4) Draw a possible segment of atactic polyacrylonitrile.
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