Organic Chemistry I Solved Exam Questions
Course Introduction
Organic Chemistry I introduces students to the fundamental principles of organic chemistry, focusing on the structure, properties, and reactivity of carbon-based compounds. The course covers topics such as bonding, molecular structure, nomenclature, stereochemistry, and the mechanisms of basic organic reactions including substitution, elimination, and addition. Emphasis is placed on the relationship between molecular structure and chemical behavior, helping students develop skills in problem-solving, understanding reaction mechanisms, and predicting outcomes of organic reactions. Laboratory techniques and safety protocols are also introduced to reinforce theoretical concepts through hands-on experience.
Recommended Textbook Organic Chemistry 8th 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) Choose the correct hybridization for the atom indicated in the molecule below. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> <sub> </sub>
A)sp
B)sp<sup>2</sup>
C)sp<sup>3</sup>
D)none of the above
Answer: C
Q2) Draw the structure of a molecule which contains only carbon and hydrogen atoms (only three of which are carbon)and in which two of the carbons are sp<sup>2</sup> hybridized and the other is sp hybridized.
Answer: H<sub>2</sub>C 11ea8a1c_2c6b_c8b5_b657_6103d91eaf4f_TB1831_00 C 11ea8a1c_2c6b_efc6_b657_6d7bd69a64e9_TB1831_00 CH<sub>2</sub>
Q3) BF<sub>3</sub> has a dipole moment of zero.Propose a structure for BF<sub>3</sub> that is consistent with this information.
Answer: BF<sub>3</sub> is trigonal planar. 11ea8a1c_2c6d_766e_b657_bfe266551fe1_TB1831_00
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) What is the conjugate base 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: B
Q2) Give the conjugate acid and the conjugate base for HSO4<sup>-</sup>:
Answer: conjugate acid: H<sub>2</sub>SO<sub>4</sub> conjugate base: SO<sub>4</sub><sup>2-</sup>
Q3) What is the pH of a 0.1 M solution of HCl? (Note: pK<sub>a</sub> for HCl is -6.)
A)6
B)-6
C)1
D)-8
E)-1
Answer: C
Q4) Write a completed equation for the acid-base pair shown below. HCO<sub>2</sub>H + <sup>-</sup>NH<sub>2</sub>
Answer: HCO<sub>2</sub>H + <sup>-</sup>NH<sub>2</sub> HCO<sub>2</sub><sup>-</sup> + NH<sub>3</sub>
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Chapter 3: An Introduction to Organic Compounds:
Nomenclature, physical Properties, and Structure
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Sample Questions
Q1) Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?
A)chair < boat < twist-boat < half-chair
B)half-chair < boat < twist-boat < chair
C)chair < twist-boat < half-chair < boat
D)chair < twist-boat < boat < half-chair
E)half-chair < twist-boat < boat < chair
Answer: D
Q2) Draw the most stable conformation of trans-1-isopropyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7e_8dda_b657_e1b785ae35ad_TB1831_00 or enantiomer
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: 11ea8a1c_2c79_f9de_b657_2fb8014d2671_TB1831_00
Q5) Draw an acceptable structure for 4-t-butyloctane.
Answer: 11ea8a1c_2c75_b3f9_b657_27e461a01963_TB1831_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) (-)-Mandelic acid has a specific rotation of -158°.What would be the specific rotation of a solution which contains 40% (-)-mandelic acid and 60% (+)-mandelic acid?
A)+95°
B)+63°
C)+32°
D)-32°
E)-63°
Q2) A and B are stereoisomers.They are nonsuperimposable and are mirror images of one another.Which of the following best describes the relationship between A and B?
A)structural isomers
B)enantiomers
C)conformational isomers
D)diastereomers
E)constitutional isomers
Q3) 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.
Q4) Draw the stereoisomers of 1,3-dichlorocyclopentane.
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6
Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
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Sample Questions
Q1) Draw the curved arrows to show how CH<sub>3</sub>CH=CHCH<sub>3</sub> reacts with HBr to form a carbocation.
Q2) Under what conditions is G° equal to H° for a chemical reaction?
Q3) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms,one ring,and one bond?
Q4) Draw the structure of propyl vinyl ether.
Q5) Identify the nucleophiles and electrophiles. <sup>-</sup>OH,BH<sub>3</sub>,H<sub>2</sub>O,<sup>+</sup>CH<sub>3</sub>,NH<su b>3</sub>,Br<sup>-</sup>
Q6) Which of the following statements about ethene,C<sub>2</sub>H<sub>4</sub>,is incorrect?
A)The H-C-H bond angles are approximately 109.5°.
B)All of the hydrogen atoms are in the same plane.
C)There is a total of five sigma bonds.
D)The carbon atoms are sp<sup>2</sup> hybridized.
E)The H-C-H bond angles are approximately 120°.
Q7) What is the molecular formula of the hydrocarbon that contains 8 carbon atoms,one ring,and two bonds?
Q8) Draw vinyl bromide. Page 7
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Chapter 6: The Reactions of Alkenes - the Stereochemistry
of Addition Reactions
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Sample Questions
Q1) What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
A)2-methylpentane
B)2-methyl-1-pentanol
C)2-methyl-2-pentanol
D)2-methyl-3-pentanol
E)1-methoxypentane
Q2) Identify the products of cis-3-methyl-3-hexene with hydrogen bromide.
A)(2R,3S)-3-bromo-3-methylhexane
B)(2R,3R)-3-bromo-3-methylhexane
C)(2S,3R)-3-bromo-3-methylhexane
D)(2S,3S)-3-bromo-3-methylhexane
E)all of the above answers
Q3) 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.
Q4) What is hyperconjugation,and how does it affect carbocation stability?
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Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
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Q1) Provide the structure of the major organic product that results when 2-butyne is treated with H<sub>2</sub> in the presence of Lindlar's catalyst.
Q2) Give the IUPAC name for HCCCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
Q3) Give the IUPAC name for (CH<sub>3</sub>)<sub>2</sub>C(CH<sub>2</sub>CH<sub>3</sub>)CCCH(CH<sub>3</ sub>)<sub>2</sub>.
Q4) What type of organic product results when 1-butyne is treated with 6M aqueous NaOH?
A)a sodium acetylide
B)an enol
C)an alcohol
D)an aldehyde
E)Not much reaction; most of the alkyne remains unchanged.
Q5) Draw an acceptable structure for acetylene.
Q6) Give the IUPAC name for BrCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>2</sub>CH<sub>3</sub>.
Q7) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q8) Draw an acceptable structure for 2-hexyne. Page 10
Q9) Draw an acceptable structure for 3-sec-butyl-1-heptyne.
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Page 11
Electronic Effects: an Introduction to the Reactions of
Benzene
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Q1) In the acetate ion (CH<sub>3</sub>CO<sub>2</sub><sup>-</sup>),which of the oxygen atoms bears a greater negative charge? Explain your answer.
Q2) Among a series of isomeric trienes,the more negative the H° of the hydrogenation reaction of a given triene,the ________ stable it is relative to the others in the isomeric series.
Q3) 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?
Q4) Which of the following is aromatic?
A)cyclopentadienyl cation
B)1,3-cyclohexadiene
C)cyclobutenyl anion
D)1,3,5-hexatriene
E)cycloheptatrienyl cation
Page 12
Q5) 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.
Q6) Show how the p orbitals overlap to form the nonbonding molecular orbital of the allyl system.
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Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
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Q1) Which of the following statements is generally true for S<sub>N</sub>1 reactions?
A)Complete inversion of configuration occurs.
B)These reactions are favored by nonpolar solvents.
C)These reactions are favored by polar solvents.
D)Reaction rates depend only on the concentration of the nucleophile.
E)The mechanism is a one-step back attack.
Q2) Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?
A)reaction products when CH<sub>3</sub>I is used as the substrate
B)reaction products when (CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>I is used as substrate
C)the stereochemistry of nucleophilic substitutions
D)the effect of nucleophile concentration on rate
Q3) Which of the following is the best leaving group?
A)HO<sup>-</sup>
B)F<sup>-</sup>
C)Cl<sup>-</sup>
D)Br<sup>-</sup>
E)I<sup>-</sup>
Page 14
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Chapter 10: Reactions of Alcohols, ethers, epoxides, amines and
Sulfur-Containing Compounds
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Q1) When dipentyl ether is treated with excess HI,through what type of mechanism(s)does the major product result?
A)S<sub>N</sub>2
B)S<sub>N</sub>1
C)both S<sub>N</sub>1 and S<sub>N</sub>2
D)E1
E)E2
Q2) 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
Q3) 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
Q4) Draw the tosylate ion and explain why it is a particularly good leaving group.
Q5) Why are alcohols typically poor electrophiles?
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Chapter 11: Organometallic Compounds
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Sample Questions
Q1) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q2) In Suzuki and Heck reactions,the vinylic and aryl halides are used as substrates in the first step because they cannot undergo A)substitution reaction. B) -elimination.
C)oxidative addition.
D)reductive elimination.
E)none of the above.
Q3) The following alkyl halide could not be used to form a Grignard reagent.Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q4) Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain briefly.
Q5) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
Q6) Name the three major alkene products that result when 1-pentene is treated with Grubbs catalyst.
Q7) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + SiCl<sub>4</sub>
Page 16
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Chapter 12: Radicals
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Sample Questions
Q1) How many radicals can one molecule of hydroquinone trap?
A)1
B)2
C)3
D)4
E)Zero
Q2) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.
Q3) During the free radical chlorination of methane,which of the following reactions has the lowest collision frequency?
A)Cl + CH<sub>3</sub> CH<sub>3</sub>Cl
B)Cl + Cl<sub>2 </sub> Cl<sub>2</sub> + Cl
C) CH<sub>3</sub> + CH<sub>4</sub> CH<sub>4</sub> + CH<sub>3</sub>
D) CH<sub>3</sub> + Cl<sub>2</sub> CH<sub>3</sub>Cl + Cl
Q4) How would you convert 1-butene to 1-butanol using radical chemistry?
Q5) Consider the reaction: CH<sub>3</sub>CH<sub>2 </sub> + Br<sub>2</sub> CH<sub>3</sub>CH<sub>2</sub>Br + Br .Given that this reaction has an activation energy of +6 kcal/mol and a H° of -22 kcal/mol,sketch a reaction-energy profile for this reaction.Label the axes and show E<sub>a</sub> and H° on your drawing.
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Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
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Q1) Which molecule below has a significant band in the IR at 3300 cm<sup>-1</sup> (medium and sharp)?
A)1-pentene
B)cyclohexane
C)2-heptyne
D)1-pentyne
E)diethyl ether
Q2) In the mass spectrum of 1,2-dichloroethane,what is the m/z of the molecular ion peak of greatest intensity?
A)94
B)96
C)98
D)100
E)102
Q3) What does "m/z" stand for and what does it mean?
Q4) How can UV spectroscopy be used to estimate the nucleotide composition of DNA?
Q5) How could you distinguish the mass spectrum of 2,2-dimethylpropane from that of isopentane?
Q6) Describe the fate of a molecule from introduction to detection in a mass spectrometer. Page 18
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Chapter 14: Nmr Spectroscopy
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Q1) Deduce the identity of the following compound from the spectral data given. C<sub>9</sub>H<sub>12</sub> : <sup>13</sup>C NMR, 21.3 (quartet),127.2 (doublet),138.0 (singlet)(ppm)
Q2) An unknown compound,C<sub>3</sub>H<sub>5</sub>Cl<sub>3</sub>,gave the following proton NMR data:
Doublet at 1.70 ppm (3H)
Multiplet at 4.32 ppm (1H)
Doublet at 5.85 ppm (1H)
What is the structure of the compound?
Q3) Predict the number of signals expected,their splitting,and their relative area in the <sup>1</sup>H NMR spectrum of CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub>.
Q4) What multiplicities are observed in the spin coupled <sup>13</sup>C NMR spectrum of 2,3-dimethyl-2-butene?
Q5) Why is Fourier transform NMR spectroscopy preferred over continuous wave as a technique for <sup>13</sup>C NMR?
Q6) Deduce the structure from the data given: C<sub>7</sub>H<sub>16</sub>O; <sup>1</sup>H NMR (integration,coupling): 0.9 (9H,s),1.5 (2H,t),3.5 (3H,s),3.8 (2H,t).
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Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid
Derivatives
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Q1) What are the products of the reaction of benzoic acid with thionyl chloride?
Q2) 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.
Q3) Why are -lactams,such as penicillins and cephalosporins,unusually reactive amides?
Q4) Provide the structure of propanoic anhydride.
Q5) Predict the major organic product of the reaction between N-methylbenzamide and sodium propanoate.
A)N-propylbenzamide
B)propyl benzoate
C)phenyl propanoate
D)benzoic propanoic anhydride
E)no reaction
Q6) Which of the following compounds has the lowest boiling point?
A)1-butanol
B)butanoic acid
C)butanenitrile
D)methyl propanoate
E)butanamide
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Chapter 16: Reactions of Aldehydes and Ketones
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Q1) Draw the structure of 3-bromobutanal.
Q2) Draw the structure of 3,3-dimethyl-4-oxopentanal.
Q3) Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H<sub>2</sub>NOH.
Q4) Diisobutylaluminum hydride (DIBALH)can be used to carry out which of the following conversions?
A)ester to aldehyde
B)carboxylic acid to ester
C)2 alcohol to ketone
D)aldehyde to carboxylic acid
E)ester to ketone
Q5) Provide the proper IUPAC name for CH<sub>3</sub>CHOHCH<sub>2</sub>COCH<sub>2</sub>C(CH<sub>3</sub>)<sub>2</ sub>CH<sub>2</sub>CH<sub>3</sub>.
Q6) Draw the structure of 4-hydroxypentanal.
Q7) Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.
Q8) Provide the proper IUPAC name for PhCH<sub>2</sub>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>2</sub>CHO.
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Chapter 17: Reactions at the -Carbon
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Q1) When the 1,7-diester
CH<sub>3</sub>O<sub>2</sub>CCH<sub>2</sub>CH<sub>2</sub>CH(CH<sub>3</sub>) CH<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?
A)an acyclic -diketone
B)an acyclic -ketoacid
C)an acyclic -diester
D)a cyclic -ketoester
E)a cyclic -diketone
Q2) Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.
Q3) How would you convert cyclohexene to 2-methylcyclohexanone?
Q4) 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
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Chapter 18: Reactions of Benzene and Substituted
Benzenes
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Q1) What is the best method for the preparation of m-dibromobenzene from benzene?
A)nitrate; Sn/HCl; NaNO<sub>2</sub>/HCl,0°C; brominate twice B)nitrate; Sn/HCl; NaNO<sub>2</sub>/HCl,0°C; brominate twice; H<sub>3</sub>PO<sub>2</sub>
C)nitrate; Sn/HCl; NaNO<sub>2</sub>/HCl,0°C; H<sub>3</sub>PO<sub>2</sub>; brominate twice
D)nitrate; brominate; Sn/HCl; NaNO<sub>2</sub>/HCl,0°C; CuBr E)brominate twice
Q2) What is the major organic product that results when benzene is treated with 1-chlorobutane and AlCl<sub>3</sub>?
A)ethylbenzene
B)1-propylbenzene
C)butylbenzene
D)sec-butylbenzene
E)isobutylbenzene
Q3) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.
Q4) Provide the structure of dibenzyl ether.
Q5) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.
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Chapter 19: More About Amines - Reactions of Heterocylic Compounds
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Q1) Provide the structure of thymine; How is it used by organisms?
Q2) Draw 2-methylpyrrolidine.
Q3) When pyrrole undergoes electrophilic aromatic substitution,at which position does substitution occur?
A)2-position
B)3-position
C)4-position
Q4) How many pyrrole rings are represented in a porphyrin ring system?
A)1
B)2
C)3
D)4
E)5
Q5) Draw 4-methylisoquinoline.
Q6) Which of the following amino acids contain a heterocyclic ring?
A)tryptophan
B)proline
C)histidine
D)alanine
E)tryptophan,proline and histidine Page 25
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Chapter 20: The Organic Chemistry of Carbohydrates
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Q1) Which of the following is disaccharide?
A)galactose
B)fructose
C)erythrose
D)lactose
E)all of the above
Q2) When D-threose is treated with NaBH<sub>4</sub>
A)a 70:30 mixture of enantiomeric alditols results.
B)a 50:50 mixture of enantiomeric alditols results.
C)a meso alditol is produced.
D)the product mixture contains two diastereomeric alditols.
E)an optically active alditol is produced.
Q3) When pure -D-glucopyranose is dissolved in water,the optical rotation of the resulting solution changes over a period of time.What is the name of this phenomenon and why does it occur?
Q4) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?
Q5) Draw the Fischer projection for the open-chain form of D-glucose.
Q6) What is the main structural difference between amylose and cellulose?
Q7) Which of the D-aldopentoses yields an optically inactive aldonic acid upon oxidation with bromine water? Explain your answer.
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Chapter 21: Amino Acids,peptides,and Proteins
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Q1) Describe how electrophoresis works.
Q2) Explain what is meant by kinetic resolution and give an example.
Q3) Provide the structure of Ala-Ser-Gly at biological pH.
Q4) -Helix of proteins is stabilized by
A)disulfide bridges.
B)hydrogen bonds.
C)electrostatic interactions.
D)hydrophobic interactioms.
E)none of the above.
Q5) Which of the following are capable of denaturing proteins?
A)organic solvents
B)detergents
C)extreme pH
D)heat
E)all of the above
Q6) What is the major force responsible for the formation of an -helix in protein secondary structure?
Q7) Draw the dipeptide Val-Tyr at pH 7.0.
Page 28
Q8) Provide the Fischer projection of L-aspartic acid.
Q9) Provide the structure of the tripeptide glu-ser-ala at pH 12.
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Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
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Sample Questions
Q1) Which of the following statements is not true about catalysts?
A)They can increase the rate of a chemical reaction.
B)They can change the mechanism of a chemical reaction.
C)They are changed in a chemical reaction.
D)They participate in a chemical reaction.
E)They can decrease the activation energy of a chemical reaction.
Q2) Explain why an intramolecular reaction resulting in the formation of five- or six-membered rings occurs more readily than the corresponding intermolecular reaction.
Q3) Give the first step of the mechanism for aldolase.
A)Fructose-1,6,-diphosphate forms an imine with a lysine residue at the active site of the enzyme.
B)A tyrosine residue functions as a base catalyst to cleave the bond between C-3 and C-4.
C)The enamine intermediate rearranges to an imine.
D)Hydrolysis of the imine releases dihydroxyacetone phosphate.
E)A molecule of glyceraldehyde-3-phosphate is expelled.
Q4) Show why typical metal-bound water has a considerably lower pKa than that of water.
Page 30
Q5) How does a base catalyst increase the rate of reaction?
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Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
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Q1) Which of the following is the sequence of steps followed by biotin-dependent enzymes,as listed below? I.Transfer of the carboxyl group from carboxybiotin to the substrate
II)Activation of bicarbonate by ATP
III)Formation of carboxybiotin
A)I,II,III
B)I,III,II
C)II,I,III
D)II,III,I
E)III,II,I
Q2) Give the purpose of coenzyme B<sub>12 </sub>in rearrangement reactions.
Q3) The common name of vitamin B<sub>1</sub> is A)niacin.
B)riboflavin.
C)thiamine.
D)biotin.
E)panthothenate.
Q4) Explain what is meant by a nucleotide and give an example.
Page 31
Q5) List the four stages of catabolism and briefly explain the significance of each.
Q6) Through what enzymatic pathway is thymine biosynthesized?
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Chapter 24: The Organic Chemistry of the Metabolic Pathways
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Sample Questions
Q1) In which stage of catabolism is the citric acid cycle found?
Q2) What coenzymes are required for the b-oxidation pathway?
A)CoASH only
B)FAD and CoASH only
C)NAD<sup>+</sup> and FAD only
D)NAD<sup>+</sup> and CoASH only
E)FAD,NAD<sup>+</sup>,and CoASH
Q3) The DG°' of the hydrolysis of ATP is ________ kJ/mol.
A)+25.2
B)+7.6
C)-1.0
D)-30.5
E)-225.8
Q4) Of the following compounds,which are consumed in any step of the glycolytic conversion of glucose to pyruvate: ATP,ADP,NAD<sup>+</sup>,NADH,FAD,FADH<sub>2</sub>,Acetyl-CoA.
Q5) Causing a burning sensation in the muscles,what compound builds up in muscle cells when glycolysis occurs under anaerobic conditions?
Q6) What is gluconeogenesis?
Q7) a-Ketoglutarate is an intermediate in the citric acid cycle.Draw its structure. Page 33
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Chapter 25: The Organic Chemistry of Lipids
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Sample Questions
Q1) Most hormones are A)phosphoglycerides.
B)terpenes.
C)squalenes.
D)prostaglandins.
E)steroids.
Q2) What is the most abundant steroid in our body?
A)cholesterol
B)aldosterone
C)hydrocortisone
D)estradiol
E)prostaglandin
Q3) Squalene is a A)monoterpene.
B)sesquiterpene.
C)diterpene.
D)triterpene.
E)carotenoid.
Q4) Why do most naturally occurring fatty acids contain an even number of carbon atoms?
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Chapter 26: The Chemistry of the Nucleic Acids
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Q1) Why is the G°' value for the hydrolysis of ATP large and negative? Give three reasons.
Q2) Which of the following statements concerning nucleic acids is not correct?
A)The enzymes that catalyze DNA synthesis are known as DNA polymerases.
B)The growing DNA polymer is synthesized in the 5' to 3' direction.
C)RNA strands are synthesized in the 3' to 5' direction.
D)In DNA the distance between the strands of the double helix is relatively constant.
E)Unlike DNA,RNA is easily cleaved because the 2'-OH group of the ribose can act as the nucleophile that cleaves the strand.
Q3) Give the second step of PCR.
A)esterification
B)strand separation
C)base-pairing of the primers
D)DNA synthesis
E)hydrolysis
Q4) Why is RNA more easily cleaved than DNA?
Q5) Draw the deaminated product of guanine.
Q6) Draw the structure of uridine.
Q7) What are stacking interactions in DNA and what purpose do they serve?
Page 36
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Chapter 27: Synthetic Polymers
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Q1) Identify the monomer(s)that undergo cationic polymerization.You may choose more than one answer.
A)styrene
B)methyl methacrylate
C)vinyl chloride
D)methyl vinyl ether
E)acrylamide
Q2) Chain-growth polymerization exhibits a marked preference for
A)tail-to-tail addition
B)head-to-head addition
C)head-to-tail addition
D)head-to-middle addition
E)middle-to-tail addition
Q3) Which of the following are characteristic of linear polyethylene?
A)They are branched polymers.
B)They are known as high-density polyethylene.
C)They are soft and flexible polymers.
D)A and B
E)A and C
Q4) ABS is a copolymer of what three monomers?
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Chapter 28: Pericyclic Reactions
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Q1) Which of the following statements about carbon migrations is correct?
A)Carbon migrations never occur by a sigmatropic rearrangement.
B)Under thermal conditions,a [1,3] carbon migration that occurs suprafacially must also occur with inversion of configuration at the migrating carbon.
C)Under thermal conditions,a [1,5] carbon migration that occurs suprafacially must also occur with inversion of configuration at the migrating carbon.
D)Under thermal conditions,a carbon migration that occurs suprafacially must occur with inversion no matter the system's symmetry.
E)B,C,and D
Q2) Under photochemical conditions,(2E,4Z)-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
Q3) What is meant by frontier orbitals?
Q4) What does LCAO stand for?
Q5) Explain what a node is and how it is formed.
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