Organic Chemistry II Review
Questions
Course Introduction
Organic Chemistry II is a continuation of introductory organic chemistry, focusing on the structure, properties, and reactivity of organic compounds. This course delves deeper into reaction mechanisms, synthetic strategies, stereochemistry, and spectroscopy, with an emphasis on functional groups such as alcohols, ethers, amines, carbonyl compounds, carboxylic acids, and their derivatives. Students will build upon foundational concepts to analyze complex reactions, predict product outcomes, and design multi-step syntheses. Laboratory work reinforces theoretical knowledge through hands-on experiments in organic synthesis, purification, and characterization techniques. This course is essential for students pursuing careers in chemistry, biology, medicine, 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) 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
Q2) How many electrons are there in the valence shell of the carbon atom of a methyl anion,CH<sub>3</sub><sup>-</sup>?
A)5
B)6
C)7
D)8
Answer: D
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Chapter 2: Polar Covalent Bonds: Acids and Bases
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Sample Questions
Q1) In aromatic nitration reactions,nitric acid (HNO<sub>3</sub>)is used in conjunction with the stronger acid,sulfuric acid,H<sub>2</sub>SO<sub>4</sub>,to form an intermediate.Which of the following could be the formula for this intermediate?
A)NO<sub>3</sub><sup>-</sup>
B)H<sub>3</sub>SO<sub>4</sub><sup>+</sup>
C)H<sub>2</sub>NO<sub>3</sub><sup>+</sup>
D)HNO<sub>2</sub>
Answer: C
Q2) 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
Q3) 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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4
Chapter 3: Organic Compounds: Alkanes and Their
Stereochemistry
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Sample Questions
Q1) 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
Q2) 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
Q3) Draw the structure of a five carbon ketone containing one tertiary carbon atom. Answer: 11ea7ca1_4b29_060a_9d3f_9d00f5d6707c_TB4938_00
Q4) Provide a line bond structure for 5-tert-butyl-2,3-dimethyloctane.
Answer: 11ea7ca1_4b28_b7e7_9d3f_c33c16f7ac50_TB4938_00
Page 5
Q5) Provide the line bond structure for 4-(2,2-dibromoethyl)-3,5-dichloroheptane.
Answer: 11ea7ca1_4b28_def9_9d3f_491dbfd6cfc3_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 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
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Chapter 5: Stereochemistry at Tetrahedral Centers
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Q1) 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
Q2) 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?
Q3) Which of the following has a plane of symmetry?
A)boot
B)laboratory beaker
C)hammer
D)both b and c
E)none of these
Q4) Refer to instructions.Does streptimidone have a meso stereoisomer? Explain.
Q5) Refer to instructions.The configuration of this carbon atom is _____.
Q6) 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) 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.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%
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Chapter 7: Alkenes and Alkynes
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Sample Questions
Q1) Draw:
(3E)-3,7-dimethylocta-1,3,6-triene
Q2) Refer to instructions.Circle the isomer of pent-2-ene that is most stable.
Q3) Alkene chemistry is dominated by what type of reaction?
A)substitution
B)electrophilic addition
C)nucleophilic addition
D)elimination
E)both b and c
Q4) 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
Q5) Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.
Q6) 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) Which set of reagents is used for the Markovnikov addition of water to an alkene without rearrangement?
A)BH<sub>3</sub>,THF followed by H<sub>2</sub>O<sub>2</sub>,NaOH B)H<sub>2</sub>O,H<sub>2</sub>SO<sub>4</sub>
C)Hg(O<sub>2</sub>CCH<sub>3</sub>)<sub>2</sub>,H<sub>2</sub>O followed by NaBH<sub>4</sub>,NaOH
D)none of these
Q2) Refer to instructions. The reaction mixture would contain a majority of which isomeric product?
Q3) Refer to instructions.Write the complete,stepwise mechanism for this reaction.Show all intermediate structures and all electron flow using arrows.
Q4) 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
Q5) Refer to instructions.Which product is the Markovnikov product?
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Chapter 9: Aromatic Compounds
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Q1) Refer to instructions.The nucleophile in the reaction is indicated by letter _____.
A)A
B)B
C)C
D)D
Q2) Which of the following compounds is aromatic?
A)ethane
B)cyclobuta-1,3-diene
C)benzene
D)cycloocta-1,3,5,7-tetraene
Q3) 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
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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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 = 101
A)C<sub>5</sub>H<sub>6</sub>Br
B)C<sub>5</sub>H<sub>12</sub>N<sub>2</sub>
C)C<sub>6</sub>H<sub>15</sub>N
D)C<sub>9</sub>H<sub>12</sub>O
Q2) 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
Q3) Which of the following peaks is not prominent in the mass spectrum of 2-methylbutan-2-ol?
A)M<sup>+</sup> - 15
B)M<sup>+</sup> - 18
C)M<sup>+</sup> - 21
D)M<sup>+</sup> - 29
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) 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
Q2) Which of the following compounds gives a <sup>1</sup>H NMR spectrum consisting of only two singlets?
A)CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub >
B)CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub> OH
C)CH<sub>3</sub>OC(CH<sub>3</sub>)<sub>2</sub>OCH<sub>3</sub>
D)CH<sub>3</sub>OCH<sub>2</sub>CH(CH<sub>3</sub>)OCH<sub>3</sub>
Q3) Nuclear magnetic resonance spectroscopy provides information about a molecule's:
A)conjugated pi electron system.
B)size and formula.
C)carbon-hydrogen framework.
D)functional groups.
Q4) Refer to instructions.Based on the mass spectral data and the IR data,what functional groups are present in this compound? Page 13
Q5) Refer to instructions.Propose a structure for this compound.
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Chapter 12: Organohalides: Nucleophilic Substitutions and Eliminations
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Sample Questions
Q1) Refer to instructions.The nucleophile in these reactions is:
A)K<sup>+</sup>
B)alkyl group
C)Br<sup>-</sup>
D)I<sup>-</sup>
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.The solvent in these reactions is:
A)nonpolar aprotic
B)polar aprotic
C)polar protic
D)nonpolar protic
Q4) Refer to instructions.Write the product that results from the indicated electron flow in the reaction,showing any resulting stereochemistry
Page 15
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Chapter 13: Alcohols,phenols,and Thiols: Ethers and Sulfides
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Sample Questions
Q1) 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
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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Sample Questions
Q1) Refer to instructions.Propose a structure consistent with the spectral data presented above.
Q2) Refer to instructions.Interpret the mass spectral data.
Q3) Refer to instructions.Identify the electrophile and nucloephile in the reaction of benzaldehyde with hydrogen cyanide.
Q4) 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
Q5) Refer to instructions.This reaction is called a(n)_____ reaction.
A)conjugate addition.
B)electrophilic addition.
C)direct addition
D)1,2-addition.
Q6) Refer to instructions.Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.
Q7) Refer to instructions.Interpret the <sup>1</sup>H NMR data.
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Chapter 15: Carboxylic Acids and Nitriles
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Q1) Draw the structure of (Z)-4-methylhex-3-enoic acid.
Q2) 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
Q3) Refer to instructions.This reaction can be described as a _____ process.
A)carbonylation
B)carboxylation
C)carbaniolation
D)cationation
Q4) 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.
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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.Compound C functions as _____ in this reaction.
A)a base scavenger
B)a solvent
C)a catalyst
D)a neutralizer
Q3) Of the following,which represents a possible direct conversion of the reactant to product shown?
A)ester to acid chloride
B)thioester to acid anhydride
C)ester to amide
D)acid anhydride to acid chloride
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) 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
Q2) Refer to instructions.Which carbonyl compound functions as the electrophile in this reaction?
A)A
B)B
C)C
Q3) Refer to instructions.This reaction is an example of:
A)a mixed Claisen condensation.
B)a Dieckman condensation.
C)a Michael reaction.
D)a mixed aldol reaction.
Q4) Refer to instructions.Indicate which hydrogens in Compound II are the most acidic.Explain your answer.
20
Q5) 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) 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 tripeptides is not hydrolysed by chymotrypsin?
A)Phe-Lys-Glu
B)Lys-Tyr-Phe
C)Gln-Ser-Phe
D)Gln-Tyr-Ser
Q2) 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
Q3) Which of the following tripeptides is not hydrolysed by trypsin?
A)Glu-Arg-Ser
B)Arg-Glu-Thr
C)Glu-Ser-Arg
D)Lys-Ser-Arg
Q4) Define isoelectric point.
Q5) Refer to instructions.Name the peptide using both the three-letter and one-letter codes.
Page 22
Q6) Refer to instructions.Identify the C-terminal amino acid and the N-terminal amino acid.
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Chapter 20: Amino Acid Metabolism
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Q1) The formation of amino acids from proteins
A)occurs during anabolism.
B)is endergonic.
C)occurs during digestion.
D)is a cellular process.
E)all of these
Q2) The carbon skeletons of specific amino acids cannot be used to replenish which of the following species associated with the citric acid cycle?
A)pyruvate
B)citrate
C)fumarate
D)succinyl CoA
E)all of these can be used
Q3) Which of the following is not an intermediate in the urea cycle?
A)arginine
B)citrulline
C)ornithine
D)lysine
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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) How many D-ketotetroses could exist?
A)none
B)one
C)two
D)four E)eight
Q3) Refer to instructions._____ a ketose and _____ an aldose with two chirality centers
A)a
B)b
C)c D)d
Q4) Refer to instructions.Which anomer is the LEAST stable? Q or Z
Q5) Refer to instructions.Place a triangle around the anomeric carbon in compound Q.
Q6) Refer to instructions.Erythrulose is ____________________.
Q7) Refer to instructions.Sorbose is ____________________.
Q8) Draw the Fisher projection of L-mannose.
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Chapter 22: Carbohydrate Metabolism
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Q1) 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
Q2) 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
Q3) When acetyl-CoA reacts with oxaloacetate to form citrate
A)a new carbon-carbon bond is formed
B)an oxidative decarboxylation reaction takes place
C)a dehydration reaction takes place
D)a rearrangement takes place
Q4) Circle the carbon atoms in the molecule of glucose shown that enter the citric acid cycle as -CH<sub>3</sub> groups.
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) 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
Q2) Which of the following processes is used to harden an oil to give a fat?
A)oxidation
B)hydrogenation
C)hydrolysis
D)hydration
Q3) Which of the following would function in a regulatory capacity?
A)aldosterone
B)androsterone
C)norethindrone
D)estradiol
Q4) The major lipid components of cell membranes are:
A)sphingolipids
B)fatty acids
C)phosphoglycerides
D)terpenoids
Q5) 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) Which of the following represents the general sequence of events in the catabolism of nucleic acids?
A)hydrolysis,dephosphorylation,cleavage of the sugar
B)cleavage of the sugar,dephosphorylation,hydrolysis
C)dephosphorylation,hydrolysis,cleavage of the sugar
D)hydrolysis,cleavage of the sugar,dephosphorylation
E)dephosphorylation,cleavage of the sugar,hydrolysis
Q2) What amino acid sequence is coded by the following segment of DNA? (5')TTA-GCC-GTA-CTA-AAA (3')
Q3) Answer the following questions.
a) If the following segment of mRNA (5') CUU-AGC-UGG-CCC (3') was changed to (5') CUU-AGC-UGG-CCU (3') how would the synthesized protein change?
b) If the following segment of mRNA (5') CUU-AGC-UGG-CCC (3') was changed to (5') CUU-AGC-UGA-CCU (3') how would the synthesized protein change?
Page 28
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