Chemistry for Life Sciences
Practice Questions
Course Introduction
Chemistry for Life Sciences introduces the fundamental concepts and principles of chemistry as they apply to biological systems. This course explores the structure and properties of atoms and molecules, chemical bonding, reactions, and energetics, with an emphasis on understanding the chemical basis of life processes. Topics include acids and bases, solutions, equilibrium, and the chemistry of biomolecules such as carbohydrates, proteins, lipids, and nucleic acids. Laboratory experiences reinforce theoretical knowledge through hands-on experiments relevant to biological and health sciences, preparing students for further study in biochemistry, physiology, 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) In drawing the Lewis structure for an organic compound,the carbon atoms should always be shown with
A)lone pairs of electrons.
B)four single bonds.
C)eight total electrons.
D)a positive charge.
E)none of these
Answer: C
Q2) 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
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
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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Q1) 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
Q2) Refer to instructions.The strongest Brønsted-Lowry base in the equation is indicated by letter _____.
A)A B)B
C)C
D)D
Answer: C
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
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Chapter 3: Organic Compounds: Alkanes and Their
Stereochemistry
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Sample Questions
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) Draw the structure of a five carbon ketone containing one tertiary carbon atom.
Answer: 11ea7ca1_4b29_060a_9d3f_9d00f5d6707c_TB4938_00
Q3) 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
Q4) Refer to instructions.Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.
Answer: 11ea7ca1_4b29_542d_9d3f_dd8eb72708f8_TB4938_00
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Chapter 4: Organic Compounds: Cycloalkanes and Their
Stereochemistry
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Q1) 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
Q2) Which of the following cycloalkanes would be the most similar to its open chain counterpart?
A)cyclodecane
B)cyclooctane
C)cyclopentane
D)cyclopropane
Q3) In cycloheptane,which of the following factors contributes the least to the stability of the ring conformation?
A)torsional strain
B)angle strain
C)steric strain
D)all of these contribute to an approximately equal degree
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Chapter 5: Stereochemistry at Tetrahedral Centers
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Q1) Refer to instructions.The configuration of this carbon atom is _____.
Q2) Which of the following is the definition of a pair of diastereomers?
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
Q3) 2.10 g of an unknown compound was dissolved in 15.00 mL of ethanol.The sample was placed in a 10.0 cm cell in a polarimeter and the angle of rotation was determined to be -18.48<sup>\(\circ\)</sup>.What is the specific rotation of this unknown and specify if the compound is levorotatory or dextrorotatory?
Q4) Refer to instructions.Assign R or S configuration to each chirality center indicated in streptimidone.
Q5) Refer to instructions.The configuration of this carbon atom is _____.
Q6) Which of the following physical properties can be used to identify a compound?
A)R
B)S
C)a
D)[a]<sub>D</sub>
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Chapter 6: An Overview of Organic Reactions
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Sample Questions
Q1) Refer to instructions.If this reaction under a given set of conditions has a K<sub>eq</sub> value of 5.67,what percent conversion to the product would be expected?
A)85%
B)5.67%
C)17%
D)15%
E)nearly 100%
Q2) Refer to instructions.Species B is:
A)a carbocation
B)a radical
C)a carbanion
D)a free radical
Q3) 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
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Chapter 7: Alkenes and Alkynes
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Q1) Refer to instructions.Calculate the degree of unsaturation for Dieldrin.
Q2) Refer to instructions.How many double bonds does dieldrin have?
Q3) Refer to instructions.Circle the isomer of pent-2-ene that is most stable.
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) A molecule has three degrees of unsaturation.In this molecule there would be
A)three rings
B)three double bonds
C)two rings and one double bond
D)one ring and two double bonds
E)any of these
Q6) Draw: (3E)-3,7-dimethylocta-1,3,6-triene
Q7) Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.
Q8) Draw: trans-4,4-dimethylpent-2-ene
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Chapter 8: Reactions of Alkenes and Alkynes
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Q1) Refer to instructions. The reaction mixture would contain a majority of which isomeric product?
Q2) What type of reaction mechanism is involved in the reaction of an alcohol with aqueous acid to give an alkene?
A)nucleophilic addition
B)electrophilic addition
C)radical addition
D)elimination
Q3) What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?
A)carbocation
B)carbanion
C)radical
D)cyclic bromonium ion
Q4) 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.
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) 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.
Q2) Draw the structure of 4-bromo-2-fluorotoluene.
Q3) Refer to instructions.The Lewis acid catalyst in the reaction is indicated by letter
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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) Which of the following bonds gives rise to a strong absorbance near 1700 cm<sup>-1</sup> in the infrared spectrum?
A)C=O
B)C-O
C)C=C
D)C-C
Q3) 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
Q4) 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 the base peak? Page 12
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Chapter 11: Structure Determination: Nuclear Magnetic
Resonance Spectroscopy
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Sample Questions
Q1) 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
Q2) How many signals appear in the broadband-decoupled <sup>13</sup>C NMR spectrum of 1,2-dibromobenzene?
A)1
B)2
C)3
D)4
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.
Page 14
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Chapter 12: Organohalides: Nucleophilic Substitutions and Eliminations
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Sample Questions
Q1) Refer to instructions.Write the product that results from the indicated electron flow in the reaction,showing any resulting stereochemistry
Q2) 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
Q3) Refer to instructions.Draw a Newman projection of the reactive conformation of the starting material.
Q4) What is the rate law for the E2 reaction of an alkyl halide (RX)with sodium ethoxide (NaOEt)in ethanol solvent (EtOH)?
A)rate = k[RX]
B)rate = k[RX]<sup>2</sup>
C)rate = k[RX][Na<sup>+</sup>]
D)rate = k[RX][OEt<sup>-</sup>]
E)rate = k[OEt<sup>-</sup>]
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Chapter 13: Alcohols,phenols,and Thiols: Ethers and Sulfides
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Q1) 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
Q2) Refer to instructions.Provide the IUPAC name for the product alcohol.
Q3) 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
Q4) Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.
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Chapter 14: Aldehydes and Ketones: Nucleophilic Addition
Reactions
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Q1) Refer to instructions.This reaction is called a(n)_____ reaction.
A)conjugate addition.
B)electrophilic addition.
C)direct addition
D)1,2-addition.
Q2) Refer to instructions.Identify the electrophile and nucloephile in the reaction of benzaldehyde with hydrogen cyanide.
Q3) Refer to instructions.Interpret the mass spectral data.
Q4) Refer to instructions.Calculate the degree of unsaturation for this compound.
Q5) Refer to instructions.What functional group is indicated by the IR data?
Q6) Refer to instructions.Interpret the <sup>1</sup>H NMR data.
Q7) 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.
Page 17
Q8) Refer to instructions.Propose a structure consistent with the spectral data presented above.
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Chapter 15: Carboxylic Acids and Nitriles
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Q1) 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
Q2) Draw the structure of (Z)-4-methylhex-3-enoic acid.
Q3) Which of the following has the highest boiling point?
A)butanoic acid
B)butan-2-ol
C)hexanoic acid
D)heptan-3-one
Q4) 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
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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.Write the complete stepwise mechanism for this reaction.Show intermediate structures and all electron flow with arrows.
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.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
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Chapter 17: Carbonyl Alpha-Substitution and Condensation
Reactions
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Q1) 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.
Q2) Refer to instructions.Write the complete stepwise mechanism for the reaction above.Show all intermediate structures and all electron flow with arrows.
Q3) How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis?
Q4) An enolate ion
A)is a resonance hybrid.
B)can be protonated to from the corresponding enol.
C)can be protonated to form the keto tautomer.
D)forms under basic conditions.
E)All of these
Q5) Refer to instructions.Which carbonyl compound functions as the electrophile in this reaction?
Page 21
Q6) How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?
Q7) Which of the following does not possess an enol form? Explain your choice.
A)A
B)B
C)C
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Chapter 18: Amines and Heterocycles
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Q1) 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?
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 the 4-methoxyanilinium ion is 5.34.What is the pK<sub>b</sub> for 4-methoxyaniline?
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Chapter 19: Biomolecules: Amino Acids,peptides,and
Proteins
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Q1) Define isoelectric point.
Q2) Refer to instructions.What fragments would result if dynorphin were cleaved by trypsin?
Q3) To what structural feature does the term "secondary 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
Q4) Which of the following amino acids would contain the highest concentration of zwitterions at pH 5.90?
A)aspartic acid (pI 2.77)
B)alanine (pI 6.01)
C)lysine (pI 9.74)
D)glutamic acid (pI 3.22)
E)all of these contain approximately equal concentrations of zwitterions
Q5) To what structural feature does the term "tertiary 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
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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) In the process of amino acid biosynthesis,how are glutamic acid,glutamine,proline,and arginine all related?
A)They are all derived from a-ketoglutarate.
B)They are all derivatives of acetyl CoA.
C)They are all derivatives of pyruvate.
D)They are all derived from aspartate.
E)They are all derivatives of 3-phosphoglycerate.
Q3) 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.
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Chapter 21: Biomolecules: Carbohydrates
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Q1) Refer to instructions.Draw both chair conformations of the a-anomer of rhamnose in its pyranose form.Circle the more stable conformation.
Q2) Refer to instructions.Sorbose is ____________________.
Q3) Refer to instructions.Which enantiomer of ribose is drawn,D or L,and is it the a or b anomer?
Q4) Which of the following is a disaccharide?
A)glucose
B)fructose
C)sucrose
D)N-acetylgalactosamine
E)both c and d
Q5) Refer to instructions.Assign R or S configuration to each chirality center in sorbose.
Q6) 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
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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 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) Circle the carbon atoms in the molecule of glucose shown that enter the citric acid cycle as -CH<sub>3</sub> groups.
Q4) Which of the reactions of the citric acid cycle requires FAD as a coenzyme?
A)the conversion of isocitrate to a-ketoglutarate
B)the conversion of a-ketoglutarate to succinyl-CoA
C)the conversion of succinate to fumarate
D)the conversion of malate to oxaloacetate
Q5) Draw and name the major product of the reaction of a-glucose with ATP.
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Chapter 23: Biomolecules: Lipids and Their Metabolism
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Q1) The major lipid components of cell membranes are:
A)sphingolipids
B)fatty acids
C)phosphoglycerides
D)terpenoids
Q2) Which of the following fatty acids has the highest melting point?
A)lauric acid
B)oleic acid
C)linoleic acid
D)linolenic acid
Q3) Which of the following processes is used to harden an oil to give a fat?
A)oxidation
B)hydrogenation
C)hydrolysis
D)hydration
Q4) Which of the following would function in a regulatory capacity?
A)aldosterone
B)androsterone
C)norethindrone
D)estradiol
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Chapter 24: Biomolecules: Nucleic Acids and Their Metabolism
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Q1) 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.
Q2) A double-stranded DNA molecule that contains 22%,on a mole basis,T must also contain
A)11% G
B)22% G
C)28% G
D)56% G
E)78% G
Q3) Base pairs in DNA are
A)parallel to each other and parallel to the long axis of the DNA molecule
B)parallel to each other and perpendicular to the long axis of the DNA molecule
C)parallel to each other,with random orientations to the long axis of the DNA molecule
D)perpendicular to each other,with every other base pair parallel to the long axis of the DNA molecule
E)perpendicular to each other,with random orientations to the long axis of the DNA molecule
Page 29
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