Organic Chemistry for Life Sciences
Exam Answer Key
Course Introduction
This course explores the fundamental concepts of organic chemistry with a focus on applications relevant to the life sciences. Topics include the structure, properties, and reactivity of organic molecules; functional groups commonly found in biological systems; reaction mechanisms; and the principles underlying the synthesis and interactions of organic compounds. Emphasis is placed on understanding how organic chemistry concepts apply to biological processes, such as enzyme catalysis, metabolic pathways, and the structure of biomolecules like proteins, nucleic acids, carbohydrates, and lipids. Through lectures, discussions, and problem-solving exercises, students gain a foundational knowledge that supports further study in biochemistry, molecular biology, and related fields.
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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Sample Questions
Q1) Consider the formation of an sp<sup>2</sup> hybrid orbital.Which of the following is true?
A)Four equivalent hybrid orbitals are produced.
B)One s and one p atomic orbital are involved.
C)One p atomic orbital remains unhybridized.
D)The hybrid orbitals produced can form p bonds.
E)none of these
Answer: C
Q2) Instructions: Propose a structure for a molecule that meets the following description. Refer to instructions.Contains only one sp<sup>3</sup> hybridized carbon and two sp<sup>2</sup> hybridized carbons.
Answer: 11ea7ca1_4b4f_a1ae_9d3f_751a4bb8316d_TB4938_00
Q3) Draw two possible isomers of C<sub>6</sub>H<sub>6</sub> in which all the carbon atoms are sp<sup>2</sup> hybridized.
Answer: 11ea7ca1_4b50_3cf9_9d3f_3bf41f82150e_TB4938_00
Q4) Draw all possible structures of CF<sub>n</sub>Cl<sub>m</sub> where n and m vary from 0 to 4.
Answer: 11ea7ca1_4b50_3cf8_9d3f_69ef67059984_TB4938_00
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Chapter 2: Polar Covalent Bonds: Acids and Bases
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Sample Questions
Q1) Refer to instructions.Using the curved arrow formalism,show the flow of electrons for this reaction.
Answer: 11ea7ca1_4b34_033f_9d3f_cd711d6f2f17_TB4938_00
Q2) Refer to instructions.Will this reaction take place as written in the forward direction? Explain.
Answer: No,the reaction will not take place as written because the strongest acid reacts with the strongest base to give the weakest conjugate acid and the weakest conjugate base.(pK<sub>a</sub> = 18).
Q3) 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
Q4) Refer to instructions.Which of the following would be common to all?
A)Lewis acids
B)Lewis bases
C)Lewis acids or bases
D)Neither Lewis acids nor bases
Answer: A
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Chapter 3: Organic Compounds: Alkanes and Their
Stereochemistry
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Sample Questions
Q1) Refer to instructions.Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.
Answer: 11ea7ca1_4b29_542d_9d3f_dd8eb72708f8_TB4938_00
Q2) Which of the following functional group classifications do not contain oxygen?
A)ether
B)thiol
C)aldehyde
D)ester
E)amide
Answer: B
Q3) The most stable conformation of an alkane occurs when
A)carbon-carbon bonds are staggered and bulky groups are gauche.
B)carbon-carbon bonds are staggered and bulky groups are anti.
C)carbon-carbon bonds are eclipsed and bulky groups are gauche.
D)carbon-carbon bonds are eclipsed and bulky groups are anti.
Answer: B
Q4) Refer to instructions.Draw a Newman projection of the anti conformation of 1,2-dichloroethane.
Answer: 11ea7ca1_4b29_2d1c_9d3f_3fc448576ec5_TB4938_00
Page 5
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Chapter 4: Organic Compounds: Cycloalkanes and Their
Stereochemistry
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Q1) Which of the following cycloalkanes has the most ring strain?
A)cyclopropane
B)cyclobutane
C)cyclopentane
D)cyclohexane
Q2) Substitution of which of the following groups on a cycloalkane would result in the greatest amount of steric strain?
A)bromo
B)ethyl
C)isopropyl
D)hydroxyl
Q3) If the 1,3-diaxial strain for an ethyl group is 4.0 kJ/mol,what is the energy difference between the axial and equatorial conformations of ethylcyclohexane?
A)2.0 kJ/mol
B)4.0 kJ/mol
C)8.0 kJ/mol
D)16.0 kJ/mol
E)Cannot be determined from the 1,3-diaxial strain
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Chapter 5: Stereochemistry at Tetrahedral Centers
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Sample Questions
Q1) Which of the following physical properties can be used to identify a compound?
A)R
B)S
C)a
D)[a]<sub>D</sub>
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) The following atoms are commonly encountered in organic molecules.For which is it not possible to isolate enantiomers due to rapid inversion?
A)trivalent phosphorus
B)trivalent nitrogen
C)divalent sulfur
D)trivalent sulfur
E)both b and c
Q4) Refer to instructions.The configuration of this carbon atom is _____.
Q5) Refer to instructions.Does streptimidone have a meso stereoisomer? Explain.
Page 7
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Chapter 6: An Overview of Organic Reactions
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Q1) Refer to instructions.Draw arrows on the structures above showing electron flow in steps two and three of this reaction.
Q2) Refer to instructions.This reaction is an example of:
A)a substitution reaction.
B)a rearrangement reaction.
C)an elimination reaction.
D)an addition reaction.
Q3) Refer to instructions.The forward and reverse reactions are classified,respectively,as:
A)addition,elimination
B)elimination,substitution
C)elimination,addition
D)elimination,rearrangement
E)substitution,addition
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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Sample Questions
Q1) A compound with the following molecular formula contains two double bonds.What is the correct subscript for H in the formula?
C<sub>10</sub>H<sub>?</sub>ClN<sub>2</sub>O
A)19
B)22
C)18
D)20
E)21
Q2) 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>
Q3) Refer to instructions.Circle the isomer of pent-2-ene that is most stable.
Q4) Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.
Q5) Refer to instructions.How many double bonds does dieldrin have?
Q6) Refer to instructions.Calculate the degree of unsaturation for Dieldrin.
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Chapter 8: Reactions of Alkenes and Alkynes
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Q1) 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.
Q2) The reaction conditions to carry out the production of cyclopentene using bromocyclopentane as the starting material would be: A)KOH,CH<sub>3</sub>CH<sub>2</sub>OH B)H<sub>2</sub>SO<sub>4</sub>,THF C)H<sub>2</sub>O<sub>2</sub>,OH<sup>-</sup> D)Hg(OAc)<sub>2</sub>,H<sub>2</sub>O
Q3) Refer to instructions. The reaction mixture would contain a majority of which isomeric product?
Q4) Refer to instructions.Which product would have a lower energy transition state for the formation of the intermediate leading to it?
Q5) Refer to instructions.Which product is the Markovnikov product?
Q6) 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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Sample Questions
Q1) Which of the following compounds is aromatic?
A)ethane
B)cyclobuta-1,3-diene
C)benzene
D)cycloocta-1,3,5,7-tetraene
Q2) Which of the following is a correct statement regarding electrophilic aromatic substitution?
A)The carbocation intermediate will lose a proton to regain aromaticity,usually from a position other than the site of electrophilic attack.
B)Formation of the carbocation intermediate has a high activation barrier due to loss of aromaticity.
C)The carbocation intermediate has several resonance structures and is negatively charged.
D)Re-formation of the aromatic ring has a low activation barrier and therefore occurs slowly.
E)Many suitable electrophiles are unreactive and can be stored for long periods of time prior to use.
Q3) 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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Sample Questions
Q1) Instructions: Select the most reasonable formula for the compounds with the following mass spectral data. Refer to instructions.M<sup>+</sup> at m/z = 216
A)C<sub>6</sub>H<sub>13</sub>OCl
B)C<sub>4</sub>H<sub>8</sub>Br<sub>2</sub>
C)C<sub>10</sub>H<sub>16</sub>
D)C<sub>9</sub>H<sub>12</sub>O
Q2) Which of the following bonds undergoes stretching at the highest frequency?
A)O-H
B)C-H
C)C=O
D)CºC
Q3) Which of the following bonds undergoes stretching at the highest frequency?
A)C=O
B)C-O
C)C=C
D)C-C
Q5) Refer to instructions.What peak represents M<sup>+</sup>? Page 12
Q4) 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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Sample Questions
Q1) Refer to instructions.Based on the mass spectral data and the IR data,what functional groups are present in this compound?
Q2) Explain why all protons in a molecule do not absorb rf energy at the same frequency.
Q3) How many positive and negative peaks appear in the DEPT-135 spectrum of 2,4-dimethylpentane?
A)two positive and one negative
B)three positive and two negative
C)four positive and three negative
D)six positive and one negative
Q4) Refer to instructions.What is the ratio of peak areas upon integration of the spectrum for A,B,and C respectively?
A)3:1:3:3
B)1:1:6
C)1:2:6
D)3:1:6
Q5) How many sets of equivalent protons are there in hexane,2-methylhexane,and 3-methylhexane,respectively?
Page 14
Q6) Refer to instructions.Propose a structure for this compound.
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Chapter 12: Organohalides: Nucleophilic Substitutions and Eliminations
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Q1) Which mechanism is favored by the reaction of a secondary alkyl bromide with potassium t-butoxide?
A)S<sub>N</sub>1
B)S<sub>N</sub>2
C)E1
D)E1<sub>CB</sub>
E)E2
Q2) Refer to instructions.Write the product that results from the indicated electron flow in the reaction,showing any resulting stereochemistry
Q3) What is the preferred stereochemistry of the E2 elimination?
A)inversion
B)retention
C)antiperiplanar
D)synperiplanar
E)gauche
Q4) Refer to instructions.The mechanism for this reaction is:
A)S<sub>N</sub>2
B)E2
C)S<sub>N</sub>1
D)E1
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Chapter 13: Alcohols,phenols,and Thiols: Ethers and Sulfides
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Sample Questions
Q1) Refer to instructions.Mechanistically,the Williamson ether synthesis outlined above is:
A)an E1 process
B)an S<sub>N</sub>1 process
C)an E2 process
D)an S<sub>N</sub>2 process
Q2) Refer to instructions.Provide the IUPAC name for the product alcohol.
Q3) Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.
Q4) Refer to instructions.The conversion of an alcohol into an alkyl chloride by reaction with SOCl<sub>2</sub> is an example of:
A)an E1 process
B)an S<sub>N</sub>1 process
C)an E2 process
D)an S<sub>N</sub>2 process
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Chapter 14: Aldehydes and Ketones: Nucleophilic Addition
Reactions
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Q1) The nucleophillic addition of water to an aldehyde or ketone
A)is irreversible.
B)dependent on the structure of the carbonyl.
C)favored by neutral conditions.
D)produces a stable tetrahedral product.
E)all of these.
Q2) Refer to instructions.This reaction is called a(n)_____ reaction.
A)conjugate addition.
B)electrophilic addition.
C)direct addition
D)1,2-addition.
Q3) Refer to instructions.What functional group is indicated by the IR data?
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.Propose a structure consistent with the spectral data presented above.
Q6) Refer to instructions.Interpret the <sup>1</sup>H NMR data. Page 17
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Chapter 15: Carboxylic Acids and Nitriles
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Q1) Which of the following has the highest boiling point?
A)butanoic acid
B)butan-2-ol
C)hexanoic acid
D)heptan-3-one
Q2) 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.
Q3) Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?
A)FCH<sub>2</sub>COOH > CH<sub>3</sub>COOH > F<sub>2</sub>CHCOOH
B)FCH<sub>2</sub>COOH > CH<sub>3</sub>COOH > CH<sub>3</sub>OH
C)CH<sub>3</sub>CH<sub>2</sub>OH > ClCH<sub>2</sub>COOH > BrCH<sub>2</sub>COOH
D)CH<sub>3</sub>COOH > ClCH<sub>2</sub>COOH > CH<sub>3</sub>OH
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) Refer to instructions.This reaction is an example of:
A)an intermolecular nucleophilic acyl substitution reaction
B)an intramolecular nucleophilic acyl substitution reaction
C)an intermolecular S<sub>N</sub>2 reaction
D)an intramolecular S<sub>N</sub>2 reaction
Q2) Refer to instructions.Compound C functions as _____ in this reaction.
A)a base scavenger
B)a solvent
C)a catalyst
D)a neutralizer
Q3) Refer to instructions.The nucleophile in this reaction is indicated by letter _____.
A)A
B)B
C)C
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) Which of the following would form an enol on treatment with an acid?
A)4-chlorobenzaldehye
B)2,2,-dimethylbutanal
C)2,2,4,4-tetrachlorohexan-3-one
D)none of these
Q2) Refer to instructions.Which carbonyl compound functions as the electrophile in this reaction?
A)A
B)B
C)C
Q3) Refer to instructions.Draw the structure of the enolate ion that is generated during the course of this reaction.
Q4) Refer to instructions.Write the complete stepwise mechanism for the reaction above.Show all intermediate structures and all electron flow with arrows.
Q5) How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?
Q6) How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis?
Page 21
Q7) Refer to instructions.Write the complete stepwise mechanism for the reaction above.Show all intermediate structures and all electron flow with arrows.
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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) 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?
Q3) Refer to instructions.Based on the pK<sub>a</sub>s for their corresponding ammonium ions,which arylamine above is the strongest base?
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Chapter 19: Biomolecules: Amino Acids,peptides,and Proteins
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Q1) Which of the following amino acids has an aromatic side chain?
A)isoleucine
B)valine
C)tyrosine
D)threonine
Q2) Refer to instructions.What fragments would result if dynorphin were cleaved by chymotropsin?
Q3) Refer to instructions.Show the steps involved in a synthesis of F-G-I using the Merrifield procedure.
Q4) Which of the following amino acids has a non-polar side chain?
A)histidine
B)arginine
C)glutamine
D)valine
Q5) To what structural feature does the term "quaternary 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
Q6) Refer to instructions.Circle the peptide bonds. Page 23
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Chapter 20: Amino Acid Metabolism
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Q1) The reaction,2 NH<sub>4</sub><sup>+</sup> + a-ketoglutarate + NADPH + ATP ® glutamine + NADP<sup>+</sup> + ADP + P<sub>i</sub> + H<sub>2</sub>O,is the combined result of what two enzymes?
A)nitrogenase and glutamate dehydrogenase (GDH)
B)GDH and glutamine synthetase (GS)
C)GS and nitrogenase
D)GDH and nitrogenase
E)all of these are correct
Q2) Ornithine serves three metabolically important roles but is not found in proteins.Which of the following statements about ornithine is not true?
A)It is a precursor in the synthesis of citrulline.
B)It is an intermediate in the urea cycle.
C)It is a precursor in the synthesis of arginine.
D)It is biosynthesized from glutamine.
E)It is a product of arginine hydrolysis.
Q3) Many biological reactions are endergonic.Explain how it is possible that these reactions occur spontaneously.
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Chapter 21: Biomolecules: Carbohydrates
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Q1) Refer to instructions.Erythrulose is ____________________.
Q2) Which of the following is a disaccharide?
A)glucose
B)fructose
C)sucrose
D)N-acetylgalactosamine
E)both c and d
Q3) Refer to instructions.Assign R or S configuration to each chirality center in sorbose.
Q4) How many D-ketotetroses could exist?
A)none
B)one
C)two
D)four
E)eight
Q5) Refer to instructions.Place a triangle around the anomeric carbon in compound Q.
Q6) Refer to instructions.Sorbose is ____________________.
Q7) Refer to instructions.Which enantiomer of ribose is drawn,D or L,and is it the a or b anomer?
Q8) Draw the Fisher projection of L-mannose.
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Chapter 22: Carbohydrate Metabolism
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Q1) In the course of the conversion of glyceraldehyde 3-phosphate to 1,3-bisphosphoglycerate
A)an alcohol group is phosphorylated
B)an alcohol is oxidized to an aldehyde
C)an alcohol is oxidized to a carboxylic acid
D)an aldehyde is oxidized to a carboxylic acid
Q2) Which of the following are not involved in both glycolysis and gluconeogenesis?
A)pyruvate
B)oxaloacetate
C)glucose-6-phosphate
D)fructose-6-phosphate
E)all of these
Q3) At the beginning of polysaccharide catabolism,a-amylase catalyzes:
A)internal (1®6)links
B)internal (1®4)links
C)terminal (1®6)links
D)terminal (1®4)links
E)all of these
Q4) Circle the carbon atoms in the molecule of glucose shown that enter the citric acid cycle as -CH<sub>3</sub> groups.
Page 27
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Chapter 23: Biomolecules: Lipids and Their Metabolism
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Q1) How many molecules of acetyl CoA are produced in the catabolism of stearic acid?
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) Chemically,these are triacylglycerols,triesters of glycerol with three long-chain carboxylic acids.
A)waxes
B)fats and oils
C)fatty acids
D)soaps
Q4) All of the following are byproducts of b-oxidation,except:
A)Acetyl CoA
B)ADP
C)NADH
D)FADH<sub>2</sub>
E)All of these are byproducts of b-oxidation.
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Chapter 24: Biomolecules: Nucleic Acids and Their Metabolism
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Q1) Describe,in general terms,the steps involved in the automated synthesis of the DNA sequence GCT.
Q2) DNA can best be described as
A)two backbones of alternating deoxyribose and nitrogenous base on the exterior,with phosphates on the interior
B)two backbones of alternating deoxyribose and nitrogenous base on the interior,with phosphates on the exterior
C)two backbones of alternating deoxyribose and phosphate on the exterior,with nitrogenous bases on the interior
D)two backbones of alternating deoxyribose and phosphate on the interior,with nitrogenous bases on the exterior
E)two backbones of alternating nitrogenous base and phosphate on the exterior,with deoxyriboses on the interior
Q3) In some instances,base pairs other than the familiar G-C and A-T matches can form.For these alternate pairs to form,one of the two bases must tautomerize.Based on this information,draw a C-A pair and determine the number of hydrogen bonds that would stabilize the pair.
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