Advanced Organic Chemistry
Mock Exam
Course Introduction
Advanced Organic Chemistry delves into the intricate mechanisms, synthetic strategies, and theoretical principles governing organic reactions. The course covers topics such as reaction kinetics, molecular orbital theory, stereochemistry, pericyclic reactions, and the reactivity of complex organic molecules. Emphasis is placed on understanding the reactivity patterns of functional groups, retrosynthetic analysis, and the application of modern spectroscopic techniques for structure elucidation. Students are also introduced to contemporary developments in organic synthesis, including organometallic chemistry, catalysis, and asymmetric synthesis, preparing them for research or advanced study in chemical sciences.
Recommended Textbook
Organic Chemistry With Biological Applications 2nd Edition by John E. McMurry
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Chapter 1: Structure and Bonding
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Q1) Instructions: Propose a structure for a molecule that meets the following description. Refer to instructions.Contains only two sp<sup>3</sup> hybridized carbons and two sp hybridized carbons.
Answer: 11ea7ca1_4b4f_7a9d_9d3f_01ae24ceffb3_TB4938_00
Q2) Which of the following statements is not true?
A)The carbon-carbon single bond of an alkane is weaker than the carbon-carbon triple bond of an alkyne.
B)The carbon-carbon triple bond of an alkyne is shorter than the carbon-carbon double bond of an alkene.
C)The carbon-carbon triple bond of an alkyne is exactly three times as strong as a carbon-carbon single bond of an alkane.
D)The carbon-carbon single bond of an alkane is longer than the carbon-carbon triple bond of an alkyne.
Answer: C
Q3) Draw the structure for CCl<sub>2</sub>F<sub>2</sub> using solid,wedged,and dashed lines to show the tetrahedral geometry.
Answer: 11ea7ca1_4b50_640a_9d3f_0dd956edf8ed_TB4938_00
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Chapter 2: Polar Covalent Bonds: Acids and Bases
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Q1) Which of the following statements is not true regarding resonance structures?
A)All resonance structures must have the same number of electrons
B)All resonance structures must differ in the hybridization of atoms.
C)All resonance structures must have the same arrangement of atoms
D)All resonance structures must be valid Lewis structures
Answer: B
Q2) Refer to instructions.Indole can function as a Lewis base in the presence of strong acid.Formulate a reaction,using a generic acid (HA),showing electron flow with arrows,that demonstrates this reactivity of indole.
Answer: 11ea7ca1_4b34_2a53_9d3f_9961c87bbbb7_TB4938_00
Q3) Refer to instructions.Indole can function as a Brønsted-Lowry acid in the presence of strong bases.Formulate a reaction,using a generic base (:B<sup>-</sup>),showing electron flow with arrows,that demonstrates this reactivity of indole.
Answer: 11ea7ca1_4b34_0341_9d3f_f787c2e12e2e_TB4938_00
Q4) Refer to instructions.Using the curved arrow formalism,show the flow of electrons for this reaction.
Answer: 11ea7ca1_4b34_033f_9d3f_cd711d6f2f17_TB4938_00
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Chapter 3: Organic Compounds: Alkanes and Their
Stereochemistry
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Sample Questions
Q1) Provide the line bond structure for 4-(2,2-dibromoethyl)-3,5-dichloroheptane.
Answer: 11ea7ca1_4b28_def9_9d3f_491dbfd6cfc3_TB4938_00
Q2) If ethane reacts with a large excess of chlorine over a long period of time,the most likely major product of the reaction would be:
A)CCl<sub>3</sub>CCl<sub>3</sub>
B)CH<sub>3</sub>CH<sub>3</sub>
C)CH<sub>2</sub>ClCH<sub>2</sub>Cl
D)CH<sub>2</sub>ClCH<sub>3</sub>
E)Ethane does not react with the halogens.
Answer: A
Q3) One of the functional group classifications is characterized by the presence of an sp<sup>2</sup> hybridized carbon atom.This functional group could be:
A)alkyl halide
B)sulfide
C)alcohol
D)aldehyde
E)alkyne
Answer: D
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Chapter 4: Organic Compounds: Cycloalkanes and Their
Stereochemistry
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Q1) Which of the following statements is not true regarding the conformation of substituted cyclohexanes?
A)ring flip of substituted cyclohexanes flips the axial and equatorial positions of substituents
B)substituted cyclohexanes are destabilized by 1,3-diaxial interactions
C)the twist-boat conformation of cyclohexane is more stable than the chair conformation
D)the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy
Q2) Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?
A)1,1-dimethylcyclohexane
B)cis-1,2-dimethylcyclohexane
C)trans-1,2-dimethylcyclohexane
D)trans-1,3-dimethylcyclohexane
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Chapter 5: Stereochemistry at Tetrahedral Centers
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Q1) If (+)-sucrose has a specific rotation of +66.47,what is the specific rotation of (-)-sucrose?
A)+66.47
B)-66.47
C)+33.43
D)-33.43
E)Must be determined with a polarimeter.
Q2) Which of the following correctly describes a molecule that is achiral?
A)Non-superimposability of the molecule on its mirror image
B)Superimposability of the molecule on its mirror image
C)Contains a carbon atom with four different substituents
D)Does not have a plane of symmetry
E)Both b and d
Q3) Refer to instructions.The configuration of this carbon atom is _____.
Q4) Which of the following is the definition of a pair of enantiomers?
A)A pair of structures that are superimposable mirror images of one another
B)A pair of stereoisomers that are non-superimposable mirror images of one another
C)A pair of stereoisomers that are not mirror images of one another
D)A pair of stereoisomers that have equal specific rotations
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Chapter 6: An Overview of Organic Reactions
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Q1) Which of the following correctly compares the two elements in terms of polarizability?
A)S > O
B)F > Br
C)N > P
D)Cl > I
Q2) Polarizability:
A)explains a nonpolar carbon-sulfur bond participating in polar reaction.
B)indicates the magnitude of a dipole moment.
C)is larger for smaller atoms with few electrons.
D)is the electric field associated with a polar bond.
E)all of these
Q3) Refer to instructions.Add curved arrows to indicate electron flow in the first step.
Q4) Which of the following is a characteristic of a polar reaction?
A)symmetrical bond making and breaking
B)one electron from each reactant forms the bond
C)involves a neutral species with an unpaired electron
D)are more common that radical reactions
E)all of these
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Chapter 7: Alkenes and Alkynes
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Q1) Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?
A)-COOH
B)-CHO
C)-CH<sub>2</sub>OH
D)-CH<sub>3</sub>
Q2) Refer to instructions.How many double bonds does dieldrin have?
Q3) Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?
A)-NH<sub>2</sub>
B)-NHCH<sub>3</sub>
C)-CH<sub>2</sub>NH<sub>2</sub>
D)-CH<sub>2</sub>NHCH<sub>3</sub>
Q4) Hydride shifts
A)occur to form less highly substituted carbocations.
B)occur by transfer of an H<sup>+</sup> between adjacent carbon atoms.
C)are observed only in single step reactions.
D)transfer positive charge to a more highly substituted carbon atom.
Q5) Draw: trans-4,4-dimethylpent-2-ene
Page 9
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Chapter 8: Reactions of Alkenes and Alkynes
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Q1) What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide?
A)nucleophilic addition
B)electrophilic addition
C)radical addition
D)elimination
Q2) What type of reaction mechanism accounts for the reaction of an alkyne with HBr to give an alkyl bromide?
A)nucleophilic addition
B)electrophilic addition
C)radical addition
D)elimination
Q3) Refer to instructions.Write the complete reaction mechanism for the first step of this reaction sequence.Show all electron flow with arrows and show all intermediate structures.
Q4) Refer to instructions. The reaction mixture would contain a majority of which isomeric product?
Q5) Refer to instructions.Write the complete,stepwise mechanism for this reaction.Show all intermediate structures and all electron flow using arrows.
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Chapter 9: Aromatic Compounds
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Q1) Which of the following does not correctly characterize a nucleophilic aromatic substitution reaction?
A)favored by electron-withdrawing groups
B)carbanion intermediates
C)-NO<sub>2</sub> and -CHO activate the ring
D)-NO<sub>2</sub> and -CHO are o/p-directors
E)an H atom is replaced on the ring
Q2) Which of the following undergoes the most rapid bromination upon treatment with Br<sub>2</sub>/FeBr<sub>3</sub>?
A)benzene
B)nitrobenzene
C)bromobenzene
D)benzaldehyde
Q3) Which of the following compounds is aromatic?
A)ethane
B)cyclobuta-1,3-diene
C)benzene
D)cycloocta-1,3,5,7-tetraene
Q4) Refer to instructions.This reaction proceeds _____________ (faster or slower)than benzene.
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Chapter 10: Structure Determination: Mass
Spectrometry,infrared Spectroscopy,and Ultraviolet Spectroscopy
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Q1) Refer to instructions.What peak represents M<sup>+</sup>?
Q2) Cyclohexene and hex-2-yne both have the molecular formula,C<sub>6</sub>H<sub>10</sub>.
a)How would you use infrared spectroscopy to distinguish between the two compounds?
b)How could the mass spectrum be used to distinguish between the two compounds?
Q3) Examining the infrared spectrum of a compound allows us to:
A)determine the types of functional groups present in the compound
B)determine the carbon-hydrogen framework of the compound
C)determine the molecular weight of the compound
D)determine the nature of the conjugated pi electron system in the compound
Q4) What is the vertical axis of a mass spectrum?
A)mass
B)energy
C)abundance
D)field strength
Q6) Refer to instructions.What peak represents the base peak? Page 12
Q5) Refer to instructions.Propose structures for fragment ions at m/z = 57,43,and 29.
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Chapter 11: Structure Determination: Nuclear Magnetic
Resonance Spectroscopy
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Q1) Which of the following would not produce nuclear magnetic resonance?
A)(<sup>2</sup>H)
B)(<sup>14</sup>N_)
C)(<sup>16</sup>O)
D)(<sup>19</sup>F)
Q2) Which of the following combinations of peaks appears in the <sup>1</sup>H NMR spectrum of 2-methylpropane?
A)two singlets
B)a singlet and a nonet
C)a singlet and a decet
D)a doublet and a decet
Q3) Refer to instructions.What is the splitting pattern for the hydrogens in 3-methylbutan-2-one labeled A,B,and C,respectively?
A)singlet,singlet,singlet
B)singlet,septet,quartet
C)singlet,septet,doublet
D)singlet,septet,doublet,doublet
Q4) Refer to instructions.Propose a structure for this compound.
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Q5) Refer to instructions.How many types of nonequivalent protons are there in this molecule?
Chapter 12: Organohalides: Nucleophilic Substitutions and Eliminations
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Q1) Which conditions favor an efficient (fast,high yield)S<sub>N</sub>2 reaction between an appropriate alkyl halide and a nucleophile with a charge?
A)high concentration of a strong nucleophile,polar protic solvent
B)high concentration of a weak nucleophile,nonpolar solvent
C)low concentration of a strong nucleophile,polar aprotic solvent
D)low concentration of a weak nucleophile,nonpolar solvent
E)high concentration of a strong nucleophile,polar aprotic solvent
Q2) Which of the following would produce a mixture of products when treated under appropriate conditions with N-bromosuccinimide?
A)oct-4-ene
B)hept-1-ene
C)4,4-dimethylcyclopentene
D)4,5-dimethylcyclohexene
E)all of these produce a mixture of products
Q3) Refer to instructions.Which of the following statements is false?
A)The kinetics of these reactions are second-order
B)The kinetics of these reactions are first-order in the nucleophile
C)The rate law would be of the form R = k[alkyl halide]<sup>2</sup>
D)The kinetics of these reactions are first-order in alkyl halide
Page 15
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Chapter 13: Alcohols,phenols,and Thiols: Ethers and Sulfides
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Q1) Which of the following ethers cannot be prepared by a Williamson ether synthesis?
A)tert-butyl phenyl ether
B)isopropyl methyl ether
C)anisole
D)tert-butyl methyl ether
Q2) Refer to instructions.If a secondary alcohol were desired as a product of the reaction,B should be replaced with
A)an ester
B)an aldehyde
C)formaldehyde (methanal)
D)a primary alcohol
Q3) Addition of chlorotrimethylsilane to an alcohol
A)results in an S<sub>N</sub>1 reaction.
B)requires acidic reaction conditions.
C)is sterically hindered by the three methyl groups.
D)results in the formation of an ether.
E)produces a more reactive species.
Q4) Refer to instructions.Provide the IUPAC name for the product alcohol.
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Chapter 14: Aldehydes and Ketones: Nucleophilic Addition
Reactions
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Q1) Refer to instructions.Identify the electrophile and nucloephile in the reaction of benzaldehyde with hydrogen cyanide.
Q2) Refer to instructions.Propose a structure consistent with the spectral data presented above.
Q3) Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base.Bases catalyze hydration by:
A)making the carbonyl group more electrophilic
B)shifting the equilibrium of the reaction
C)making the carbonyl group less electrophilic
D)converting the water to hydroxide ion,a much better nucleophile
Q4) Refer to instructions.The product of this reaction is called:
A)an ylide
B)an acetal
C)a gem diol
D)a hydrate
Q5) Refer to instructions.Interpret the <sup>1</sup>H NMR data.
Q6) Refer to instructions.Interpret the mass spectral data.
Q7) Refer to instructions.What functional group is indicated by the IR data?
Q8) Refer to instructions.Calculate the degree of unsaturation for this compound. Page 17
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Chapter 15: Carboxylic Acids and Nitriles
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Q1) Refer to instructions.This compound is known to contain both a -C=O group and an -OH group.Based on this spectrum,this compound would be classified as:
A)aromatic carboxylic acid
B)aliphatic carboxylic acid
C)carbonyl containing an alcohol functional group
D)either a or b
Q2) Refer to instructions.This reaction can be described as a _____ process.
A)carbonylation
B)carboxylation
C)carbaniolation
D)cationation
Q3) Which of the following does not represent a similarity between nitriles and carboxylic acids?
A)contain 3 carbon bonds to an electronegative element
B)contain two p bonds.
C)act as electrophiles
D)undergo nucleophilic substitution reactions
E)all of these are characteristic of both nitriles and carboxylic acids.
Q4) Draw the structure of (Z)-4-methylhex-3-enoic acid.
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Chapter 16: Carboxylic Acid Derivatives: Nucleophilic Acyl
Substitution Reactions
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Q1) Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?
A)elimination followed by addition
B)addition followed by decarboxylation
C)addition followed by elimination
D)substitution followed by addition
Q2) Refer to instructions.The purpose of the base catalyst in this reaction is:
A)to polarize the carbonyl group to make it more electrophilic
B)to convert the ester to an intermediate carboxylic acid
C)to convert the alcohol group to an alkoxide anion,which is a better nucleophile
D)all of these
Q3) Refer to instructions.The product of this reaction is:
A)a lactone
B)an anhydride
C)a lactam
D)an ether
Q4) Refer to instructions.Write the complete stepwise mechanism for this reaction.Show intermediate structures and all electron flow with arrows.
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Chapter 17: Carbonyl Alpha-Substitution and Condensation Reactions
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Q1) Refer to instructions.Underline the acidic hydrogen atoms in each of the molecules.
Q2) Refer to instructions.Choose the most acidic compound from Compounds IIV.Explain your choice.
Q3) Refer to instructions.Draw the structures of the ketone and amine products of this reaction.
Q4) How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis?
Q5) Refer to instructions.Conversion of B into C involves hydrolysis of the ester followed by decarboxylation.On the structures provided below,show the electron flow for the decarboxylation step.
Q6) Refer to instructions.Draw the structure of the enolate ion that is generated during the course of this reaction.
Q7) Refer to instructions.Underline all the acidic hydrogen atoms in Compounds I through IV.
Q8) How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?
Q10) How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis? Page 21
Q9) Refer to instructions.Draw the structure of the enolate ion that is generated during the course of this reaction.
Q11) How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?
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Chapter 18: Amines and Heterocycles
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Q1) The pK<sub>a</sub> of the 4-methoxyanilinium ion is 5.34.What is the pK<sub>b</sub> for 4-methoxyaniline?
Q2) Refer to instructions.Based on the pK<sub>a</sub>s for their corresponding ammonium ions,which arylamine above is the strongest base?
Q3) The pK<sub>a</sub> of aniline is 6.15.What percent exists in the neutral and protonated forms in a 0.00100 M solution of aniline at pH 5.75?
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Chapter 19: Biomolecules: Amino Acids,peptides,and Proteins
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Q1) Refer to instructions.Circle the peptide bonds.
Q2) How does phenyl isothiocyanate,Ph-N=C=S,react with a peptide in the Edman degradation?
A)the sp carbon acts as an electrophile in a reaction with an amino group of the peptide
B)the sulfur acts as a nucleophile and adds to the carbon of the peptide bond
C)the nitrogen acts as a nucleophile and adds to the carbon of the peptide bond
D)the sp carbon acts as an electrophile in a reaction with a carboxylate of the peptide
Q3) Which of the following reagents can be used to cleave a tert-butoxycarbonyl (Boc)protecting group from a peptide?
A)H<sub>2</sub>/Pd
B)CF<sub>3</sub>CO<sub>2</sub>H
C)Na<sub>2</sub>CO<sub>3</sub>,H<sub>2</sub>O
D)LiAlH<sub>4</sub>
Q4) To what structural feature does the term "primary structure" refer?
A)the sequence of amino acids in proteins
B)the overall folding pattern of proteins
C)the aggregation of polypeptides
D)the conformation of local regions of polypeptides
Page 24
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Chapter 20: Amino Acid Metabolism
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Q1) Aspartate is formed from transamination of:
A)asparagine
B)aspartame
C)oxaloacetate
D)citrate
E)a-ketoglutarate
Q2) Suppose that the formation of a dipeptide is endergonic by +14.7 kJ/mol.If this reaction is coupled with the hydrolysis of ATP,will the net reaction be spontaneous or nonspontaneous? Explain your answer.
Q3) Which of the following is not an intermediate in the urea cycle?
A)arginine
B)citrulline
C)ornithine
D)lysine
Q4) Transamination of pyruvate with glutamate as the nitrogen donor gives:
A)alanine
B)serine
C)cysteine
D)aspartate
E)tyrosine
25
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Chapter 21: Biomolecules: Carbohydrates
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Q1) Refer to instructions.Place a triangle around the anomeric carbon in compound Q.
Q2) Refer to instructions.Provide the complete name for the a-anomer of rhamnose in its pyranose form.
Q3) Refer to instructions._____ a dextrorotary hexose and ______ a levorototary tetrose.
A)a
B)b
C)c
D)d
Q4) How many D-ketotetroses could exist?
A)none
B)one
C)two
D)four
E)eight
Q5) Draw an aldopentose with S,S,R stereochemistries at its carbons 2 through 4.
Q6) Refer to instructions.Which anomer is the LEAST stable? Q or Z
Q7) Refer to instructions.Classify ribose by carbonyl type and number of carbons.
Q8) Refer to instructions.Erythrulose is ____________________.
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Chapter 22: Carbohydrate Metabolism
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Q1) The order of compounds and intermediates found in the citric acid cycle is as follows:
A)Iso-Citrate ® Aconitate ® a-Ketoglutarate ® Fumarate ® Malate ® Oxaloacetate
B)Aconitate ® iso-Citrate ® Oxaloacetate ® a-Ketoglutarate ® Malate ® Fumarate
C)Aconitate ® iso-Citrate ® a-Ketoglutarate ® Fumarate ® Malate ® Oxaloacetate
D)Aconitate ® iso-Citrate ® a-Ketoglutarate ® Malate ® Fumarate ® Oxaloacetate
E)Iso-Citrate ® Aconitate ® a-Ketoglutarate ® Malate ® Oxaloacetate ® Fumarate
Q2) Which enzymes in the citric acid cycle catalyze oxidative decarboxylation reactions?
A)isocitrate dehydrogenase and the a-ketoglutarate dehydrogenase complex
B)aconitase and succinate dehydrogenase
C)the a-ketoglutarate dehydrogenase complex and succinate thiokinase
D)fumarase and succinate dehydrogenase
Q3) Circle the carbon atoms in the molecule of glucose shown that enter the citric acid cycle as -CH<sub>3</sub> groups.
Q4) In the reaction catalyzed by aldolase,the substrate is bound to the enzyme
A)by an ester linkage
B)as a Schiff base
C)by a peptide bond
D)by hydrogen bonds
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Chapter 23: Biomolecules: Lipids and Their Metabolism
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Q1) Chemically,these are triacylglycerols,triesters of glycerol with three long-chain carboxylic acids.
A)waxes
B)fats and oils
C)fatty acids
D)soaps
Q2) The source of oxygen for b-oxidation is:
A)CO<sub>2</sub>
B)O<sub>2</sub>
C)Peroxide
D)Water
E)None of these is the source of oxygen for b-oxidation.
Q3) Which of the following would function in a regulatory capacity?
A)aldosterone
B)androsterone
C)norethindrone
D)estradiol
Q4) How many passages through the b-oxidation pathway are required to completely degrade the following fatty acid?
CH<sub>3</sub>(CH<sub>2</sub>)<sub>12</sub>CO<sub>2</sub>H
Page 28
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Chapter 24: Biomolecules: Nucleic Acids and Their Metabolism
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Q1) Rank DNA,mRNA,and tRNA from largest to smallest.
A)DNA > mRNA > tRNA
B)DNA > tRNA > mRNA
C)mRNA > tRNA > DNA
D)mRNA > DNA > tRNA
E)tRNA > mRNA > DNA
Q2) Which of the following characterizes the polymerase chain reaction (PCR)?
A)produces multiple copies of DNA segments
B)requires small amount of the source DNA
C)the key to the process is a thermally stable enzyme
D)involves temperature cycling
E)all of these
Q3) What amino acid sequence is coded by the following segment of DNA? (5')TTA-GCC-GTA-CTA-AAA (3')
Q4) What mRNA sequence is complementary to the following DNA base sequence? (5')TAAGGCGATA (3')
Q5) What sequence of bases on the second strand of DNA is complementary to the following? (5')GCATTA (3')
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