Biological Chemistry
Practice Exam
Course Introduction
Biological Chemistry explores the chemical principles and processes that govern living systems. This course examines the structure and function of biological molecules such as proteins, nucleic acids, lipids, and carbohydrates, and their roles in metabolic pathways and cellular regulation. Students will learn about enzyme mechanisms, energy production, signal transduction, and the molecular basis of physiological processes. Emphasizing both theoretical concepts and practical laboratory techniques, the course provides a foundation for understanding the chemical basis of life and its applications in biotechnology, medicine, and research.
Recommended Textbook
Organic Chemistry With Biological Applications 2nd Edition by John E. McMurry
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Page 2
Chapter 1: Structure and Bonding
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Sample Questions
Q1) Instructions: Write valid Lewis (electron-dot)structures for each formula below.Show all electrons as dots and show all nonbonding electrons. Write: CH<sub>3</sub>CH<sub>2</sub>OH ethanol
Answer: 11ea7ca1_4b4f_0561_9d3f_35bab2410b8c_TB4938_00
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) 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
Q4) 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) 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
Q2) Which of the following molecules would exhibit the largest dipole moment?
A)CH<sub>3</sub>CH<sub>3</sub>
B)CH<sub>3</sub>CH<sub>2</sub>F
C)CH<sub>3</sub>CH<sub>2</sub>Cl
D)CH<sub>3</sub>CH<sub>2</sub>Br
Answer: B
Q3) Refer to instructions.Using the curved arrow formalism,show the flow of electrons for this reaction.
Answer: 11ea7ca1_4b34_033f_9d3f_cd711d6f2f17_TB4938_00
Q4) Refer to instructions.Indole can function as a BrĂžnsted-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
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Chapter 3: Organic Compounds: Alkanes and Their
Stereochemistry
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Q1) 4-ethyl-3,3,4-trimethylheptane could be classified as:
A)an alkane
B)saturated
C)aliphatic
D)a paraffin
E)all of these
Answer: E
Q2) How many constitutional isomers are there with the molecular formula C<sub>6</sub>H<sub>14</sub>?
A)3
B)4
C)5
D)8
Answer: C
Q3) Draw the structure of a five carbon ketone containing one tertiary carbon atom.
Answer: 11ea7ca1_4b29_060a_9d3f_9d00f5d6707c_TB4938_00
Q4) Refer to instructions.Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.
Answer: 11ea7ca1_4b29_542d_9d3f_dd8eb72708f8_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 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) In which of the following compounds would the carbon-carbon bond angle diverge the greatest from 109<sup>\(\circ\)</sup>?
A)cyclodecane
B)cyclooctane
C)cyclopentane
D)cyclopropane
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Chapter 5: Stereochemistry at Tetrahedral Centers
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Q1) Which of the following statements is true regarding pairs of enantiomers?
A)They have identical melting points
B)They have identical boiling points.
C)They rotate plane-polarized light in opposite directions
D)They produce different products in reactions with chiral reagents
E)all of these
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) Rank the following substituent groups from highest to lowest priority according to the sequencing rules.
CO<sub>2</sub>CH<sub>3</sub> CO<sub>2</sub>H OH Cl
Q4) Refer to instructions.The configuration of this carbon atom is _____.
Q5) Refer to instructions.Does streptimidone have a meso stereoisomer? Explain.
Q6) Refer to instructions.Assign R or S configuration to each chirality center indicated in streptimidone.
Q7) Refer to instructions.The configuration of this carbon atom is _____.
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Chapter 6: An Overview of Organic Reactions
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Q1) 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
Q2) In an organic reaction,which of the following is most likely to function as only a nucleophile?
A)BF<sub>3</sub>
B)(CH<sub>3</sub>)<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
C)Fe<sup>2+</sup>
D)CH<sub>3</sub>CH<sub>2</sub>S<sup>-</sup>
E)both a and c
Q3) Refer to instructions.Species B is:
A)a carbocation
B)a radical
C)a carbanion
D)a free radical
Q4) Identify and predict:
mustard gas
Cl-CH<sub>2</sub>CH<sub>2</sub>-S-CH<sub>2</sub>CH<sub>2</sub>-Cl
Page 8
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Chapter 7: Alkenes and Alkynes
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Q1) Alkene chemistry is dominated by what type of reaction?
A)substitution
B)electrophilic addition
C)nucleophilic addition
D)elimination
E)both b and c
Q2) 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
Q3) Draw:
(3E)-3,7-dimethylocta-1,3,6-triene
Q4) Calculate the degree of unsaturation in the formula below.Show your calculations. caffeine,C<sub>8</sub>H<sub>10</sub>N<sub>4</sub>O<sub>2</sub>
Q5) Refer to instructions.How many double bonds does dieldrin have?
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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 alkyne with HBr to give an alkyl bromide?
A)nucleophilic addition
B)electrophilic addition
C)radical addition
D)elimination
Q2) Refer to instructions.Write the complete,stepwise mechanism for this reaction.Show all intermediate structures and all electron flow using arrows.
Q3) Refer to instructions. The reaction mixture would contain a majority of which isomeric product?
Q4) 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
Q5) Refer to instructions.Which product would have a lower energy transition state for the formation of the intermediate leading to it?
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Chapter 9: Aromatic Compounds
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Q1) An accurate description of the structure of benzene is:
A)The p bonds are quickly moving around the ring.
B)There are two distinct structures that are in equilibrium.
C)All the carbon-carbon bonds are equal in length.
D)There are distinct single and double bonds.
E)Some bonds are longer than others.
Q2) Refer to instructions.The Lewis acid catalyst in the reaction is indicated by letter
A)A
B)B
C)C
D)D
Q3) Draw the structure of 4-bromo-2-fluorotoluene.
Q4) Which of the following compounds is aromatic?
A)ethane
B)cyclobuta-1,3-diene
C)benzene
D)cycloocta-1,3,5,7-tetraene
Q5) Refer to instructions. Draw the structure of product D.
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Chapter 10: Structure Determination: Mass
Spectrometry,infrared Spectroscopy,and Ultraviolet Spectroscopy
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Q1) What is the horizontal axis of a mass spectrum?
A)mass
B)mass/energy
C)mass/charge
D)charge
Q2) Which of the following bonds undergoes stretching at the highest frequency?
A)O-H
B)C-H
C)C=O
D)CÂșC
Q3) Which of the following statements best describes the base peak in a mass spectrum?
A)The peak from the most stable radical.
B)The peak from the species that has the isotope with the highest atomic number.
C)The peak of highest intensity.
D)The peak from the molecule minus an electron.
E)The M +1 peak
Q5) Refer to instructions.What peak represents the base peak? Page 12
Q4) Refer to instructions.What peak represents M<sup>+</sup>?
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Chapter 11: Structure Determination: Nuclear Magnetic
Resonance Spectroscopy
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Sample Questions
Q1) Explain why all protons in a molecule do not absorb rf energy at the same frequency.
Q2) A compound with the molecular formula C<sub>6</sub>H<sub>4</sub>ClBr produces only two doublets in the <sup>1</sup>H NMR spectrum.
a)Propose a structure for this compound.
b)How many signals would be present in the <sup>13</sup>CNMR for this structure?
Q3) Refer to instructions.How many types of nonequivalent protons are there in this molecule?
Q4) Which of the following compounds gives a <sup>1</sup>H NMR spectrum consisting of only a singlet and two signals in the <sup>13</sup>C NMR?
A)1,1-dibromopropane
B)1,2-dibromopropane
C)1,3-dibromopropane
D)2,2-dibromopropane
Q5) Refer to instructions.Describe each signal in terms of its integration,splitting and chemical shift.
Q6) Refer to instructions.Based on the mass spectral data and the IR data,what functional groups are present in this compound?
Page 14
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Chapter 12: Organohalides: Nucleophilic Substitutions and Eliminations
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Sample Questions
Q1) 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
Q2) Refer to instructions.The nucleophile in these reactions is:
A)K<sup>+</sup>
B)alkyl group
C)Br<sup>-</sup>
D)I<sup>-</sup>
Q3) 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
Page 15
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Chapter 13: Alcohols,phenols,and Thiols: Ethers and Sulfides
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Sample Questions
Q1) Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.
Q2) Instructions: To answer the following question(s),consider the reaction below.
Refer to instructions.The alcohol product is classified as a:
A)1<sup>\(\circ\)</sup> alcohol
B)2<sup>\(\circ\)</sup> alcohol
C)3<sup>\(\circ\)</sup> alcohol
D)4<sup>\(\circ\)</sup> alcohol
Q3) 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
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.The electrophile,the nucleophile and the catalyst in this reaction are indicated by letters _____,_____,and _____,respectively.
A)A
B)B
C)C
D)D
Q2) Refer to instructions.The reaction of an aldehyde with hydrogen cyanide is an example of _____ reaction.
A)a nucleophilic substitution
B)an electrophilic addition
C)an electrophilic substitution
D)a nucleophilic addition
Q3) Refer to instructions.Interpret the mass spectral data.
Q4) Refer to instructions.This reaction is called a(n)_____ reaction.
A)conjugate addition.
B)electrophilic addition.
C)direct addition
D)1,2-addition.
Page 17
Q5) Refer to instructions.Calculate the degree of unsaturation for this compound.
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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) Draw the structure of (Z)-4-methylhex-3-enoic acid.
Q3) 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
Q4) 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
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Chapter 16: Carboxylic Acid Derivatives: Nucleophilic Acyl
Substitution Reactions
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Q1) Refer to instructions.The product of this reaction is:
A)a lactone
B)an anhydride
C)a lactam
D)an ether
Q2) Refer to instructions.Write the complete stepwise mechanism for this reaction.Show intermediate structures and all electron flow with arrows.
Q3) Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?
A)anhydrides > amides > acid chlorides
B)amides > acid chlorides > anhydrides
C)anhydrides > acid chlorides > amides
D)acid chlorides > anhydrides > amides
Q4) Refer to instructions.Compound C functions as _____ in this reaction.
A)a base scavenger
B)a solvent
C)a catalyst
D)a neutralizer
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Chapter 17: Carbonyl Alpha-Substitution and Condensation Reactions
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Sample Questions
Q1) Refer to instructions.This reaction is an example of:
A)an intramolecular Claisen condensation
B)an intramolecular aldol condensation
C)a Robinson annulation
D)a Michael reaction
Q2) How many different aldols (b-hydroxyaldehydes),including constitutional isomers and stereoisomers,are formed upon treatment of butanal with base?
A)1
B)2
C)3
D)4
Q3) Refer to instructions.Underline the acidic hydrogen atoms in each of the molecules.
Q4) Refer to instructions.Rank the molecules above in order of increasing acidity (least acidic to most acidic).
A)III,II,I
B)II,III,I
C)I,II,III
D)II,I,III
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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 a non-polar side chain?
A)histidine
B)arginine
C)glutamine
D)valine
Q2) Which of the following amino acids has a sulfur-containing side chain?
A)serine
B)cysteine
C)lysine
D)methionine
E)both b and d
Q3) Refer to instructions.What fragments would result if dynorphin were cleaved by trypsin?
Q4) 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>
Q5) Define isoelectric point.
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Chapter 20: Amino Acid Metabolism
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Q1) Which of the following is not an intermediate in the urea cycle?
A)arginine
B)citrulline
C)ornithine
D)lysine
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) A coenzyme frequently encountered in transamination reactions is
A)tetrahydrofolate
B)pyridoxal phosphate
C)thiamine pyrophosphate
D)biotin
Q4) Transamination of pyruvate with glutamate as the nitrogen donor gives:
A)alanine
B)serine
C)cysteine
D)aspartate
E)tyrosine
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Chapter 21: Biomolecules: Carbohydrates
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Q1) How many D-ketotetroses could exist?
A)none
B)one
C)two
D)four
E)eight
Q2) Refer to instructions.Which enantiomer of ribose is drawn,D or L,and is it the a or b anomer?
Q3) Refer to instructions.Place a triangle around the anomeric carbon in compound Q.
Q4) The brick-red color observed when Benedict's test is applied to D-mannose is due to
A)the reduced form of the Cu<sup>2+</sup> reagent
B)the reduced form of the D-mannose
C)the oxidized form of the Cu<sup>2+</sup> reagent
D)the oxidized form of the D-mannose
E)products in the mixture other than those listed
Q5) Refer to instructions.Classify ribose by carbonyl type and number of carbons.
Q6) Draw an aldopentose with S,S,R stereochemistries at its carbons 2 through 4.
Q7) Refer to instructions.Draw both chair conformations of the a-anomer of rhamnose in its pyranose form.Circle the more stable conformation.
Page 24
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Chapter 22: Carbohydrate Metabolism
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Q1) Thiamin diphosphate (TPP)is a coenzyme
A)frequently encountered in oxidation-reduction reactions
B)required for the phosphorylation of ADP
C)involved in transfers of two-carbon groups
D)involved in transfers of one-carbon groups
Q2) Which enzyme catalyzes a reaction that is a major control point for glycolysis?
A)Glyceraldehyde-3-phosphate dehydrogenase
B)Enolase
C)Phosphofructokinase
D)Aldolase
Q3) The reaction of fructose 1,6-bisphosphate to give glyceraldehyde-3-phosphate and dihydroxyacetone phosphate is an example of
A)a reverse aldol condensation
B)hydrolysis
C)oxidation
D)dehydration
Q4) Draw and name the major product of the reaction of a-glucose with ATP.
Q5) Refer to instructions.This reaction proceeds through a common enol structure.Draw the structure of the glucose/fructose enol.
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Chapter 23: Biomolecules: Lipids and Their Metabolism
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Q1) All of the following describe b-oxidation,except:
A)Two-carbon units are eliminated during each cycle.
B)The process employs NAD<sup>+</sup> as an oxidant.
C)The process is the primary route to fatty acid degradation.
D)The 2-carbon groups are eliminated from the methyl end of the fatty acid.
E)Fatty acids are attached to coenzyme A during the process.
Q2) Which of the following fatty acids has the highest melting point?
A)lauric acid
B)myristic acid
C)palmitic acid
D)stearic acid
Q3) 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.
Q4) How many molecules of acetyl CoA are produced in the catabolism of stearic acid?
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Chapter 24: Biomolecules: Nucleic Acids and Their Metabolism
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Q1) What mRNA sequence is complementary to the following DNA base sequence? (5')TAAGGCGATA (3')
Q2) 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
Q3) What is the anticodon sequence in tRNA that corresponds the following segment of mRNA?
(5')CUU-AGC-UGG-CCC(3')
Q4) What amino acid sequence is coded by the following segment of DNA?
(5')TTA-GCC-GTA-CTA-AAA (3')
Q5) The phosphodiester linkages in DNA and in RNA are,respectively:
A)2' to 3',3' to 2'
B)2' to 5',5' to 2'
C)3' to 5',5' to 3'
D)3' to 5',3' to 5'
E)5' to 5',3' to 3'
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