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Introduction to Organic Chemistry offers a foundational exploration of the structure, properties, and reactions of organic molecules. This course covers essential topics such as bonding, molecular geometry, functional groups, stereochemistry, reaction mechanisms, and the synthesis of organic compounds. Students will develop skills in interpreting chemical structures, understanding reaction pathways, and applying analytical techniques to solve problems in organic chemistry. The course provides a critical basis for further study in chemistry, biology, medicine, and related fields.
Recommended Textbook
Organic Chemistry 7th Edition by William H. Brown
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Q1) What is the approximate strength of the C-C bond of ethane?
A)376 kJ/mol (90 kcal./mol)
B)422 kJ/mol (101 kcal./mol)
C)556 kJ/mol (133 kcal./mol)
D)727 kJ/mol (174 kcal./mol)
Answer: A
Q2) What is the ground-state electronic configuration of a fluoride anion (fluorine: atomic number 9)?
A)1s<sup>2</sup>2s<sup>2</sup>2p<sup>2</sup>
B)1s<sup>2</sup>2s<sup>2</sup>2p<sup>5</sup>
C)1s<sup>2</sup>2s<sup>2</sup>2p<sup>6</sup> D)1s<sup>2</sup>2s<sup>2</sup>2p<sup>7</sup>
Answer: C
Q3) Draw bond-line structures of all of the tertiary (3<sup>\(\circ\)</sup>) amines that have the formula C<sub>5</sub>H<sub>11</sub>N.
Answer: 11ea7d75_f5da_bd13_b9bd_136ab4437de0_TB1813_00_TB1813_00
Q4) Draw bond-line structures of all of the ketones that have the formula C<sub>5</sub>H<sub>10</sub>O.
Answer: 11ea7d75_f5da_95ff_b9bd_31a971c76bdd_TB1813_00_TB1813_00
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Q1) Which of the following cycloalkanes has the largest heat of combustion?
A)cyclopropane
B)cyclobutane
C)cyclopentane
D)cyclohexane
Answer: D
Q2) Which of the following alkanes has the highest boiling point?
A)propane
B)butane
C)pentane
D)hexane
Answer: D
Q3) 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)cis-1,3-dimethylcyclohexane
Answer: C
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Q1) ______________ are stereoisomers that are not mirror images.
Answer: Diastereomers diastereomers
Q2) How many stereoisomers of 2,4-pentanediol, CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH(OH)CH<sub>3</sub>, exist?
A)1
B)2
C)3
D)4
Answer: C
Q3) Which of the following compounds is a meso compound?
A)(2R,3R)-dibromobutane
B)(2R,3S)-dibromobutane
C)(2R,3S)-3-bromo-2-butanol
D)(2R,3R)-3-bromo-2-butanol
Answer: B
Q4) What mass of (S)-(-)-mandelic acid is present in a 10 g sample which has an enantiomeric excess of 30% of the S-enantiomer?
Answer: 6.5 g
Q5) The process that separates enantiomers is called ______________.
Answer: resolution
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Q1) Which of the following compounds has the lowest pK<sub>a</sub>?
A)H<sub>2</sub>O
B)HBr
C)NH<sub>3</sub>
D)CH<sub>4</sub>
Q2) Provide a brief explanation, based on features of the molecules, for the following trend in pK<sub>a</sub> values?
CH<sub>3</sub>CH<sub>2</sub>OH > CF<sub>3</sub>CH<sub>2</sub>OH ethanol 2,2,2-trifluoromethanol
15.9 12.4
Q3) Which of the following is easiest to deprotonate?
A)CH<sub>4</sub>
B)CH<sub>3</sub>CH<sub>3</sub>
C)CH<sub>2</sub>=CH<sub>2</sub>
D)HC\(\equiv\)CH
Q4) Which of the following anions is the strongest base?
A)CH<sub>3</sub>COO<sup>-</sup>
B)HO<sup>-</sup>
C)NH<sub>2</sub><sup>-</sup>
D)Cl<sup>-</sup>

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Sample Questions
Q1) Which of the following compounds is most reactive (least stable)?
a.(Z)-cycloheptene
b.(E)-cycloheptene
c.(Z)-cyclooctene
d.(E)-cyclooctene
A)True
B)False
Q2) Which of the following does not correspond to a molecular formula of a neutral compound?
A)C<sub>6</sub>H<sub>9</sub>NO<sub>2</sub>
B)C<sub>5</sub>H<sub>7</sub>N<sub>2</sub>O<sub>2</sub>
C)C<sub>8</sub>H<sub>12</sub>O<sub>3</sub>
D)C<sub>7</sub>H<sub>7</sub>N
Q3) A compound likely to be a liquid at room temperature is represented by the letter ______.
Q4) What is the approximate value of the C-C-C bond angle in propene?
A)90<sup>\(\circ\)</sup>
B)109<sup>\(\circ\)</sup>
C)120<sup>\(\circ\)</sup>
D)180<sup>\(\circ\)</sup>

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Q1) Which of the following reactions of alkenes takes place with syn stereospecificity?
A)addition of bromine (treatment with Br<sub>2</sub>)
B)hydrogenation (treatment with H<sub>2</sub>/Pt)
C)addition of HBr (treatment with HBr)
D)acid-catalyzed hydration (treatment with aqueous H<sub>2</sub>SO<sub>4</sub>)
Q2) Br<sub>2 </sub>in CCl<sub>4</sub> can be used to distinguish cyclohexene from cyclohexane.
A)True
B)False
Q3) The products obtained by the acid-catalyzed hydration of 1-methylcyclohexene and methylenecyclohexene are identical.
A)True
B)False
Q4) Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to propene?
A)the relative stability of carbocations
B)the nucleophilicity of bromide anion
C)the acidity of HBr
D)the aufbau principle
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Q1) What is the IUPAC name of the following compound?
(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>-C\(\equiv\)CH(CH<sub>3</sub>)< sub>2</sub>
A)2,6-dimethyl-3-heptyne
B)2,6-dimethyl-4-heptyne
C)1,1,5,5-tetramethyl-2-pentyne
D)4-nonyne
Q2) Which of the following reagents react with 2-butyne to form butane
A)H<sub>2</sub>/Lindlar catalyst
B)H<sub>2</sub>/Pd
C)(sia)<sub>2</sub>BH followed by CH<sub>3</sub>COOH D)Na/NH<sub>3</sub>
Q3) What type of intermediate is formed in the Hg<sup>2</sup><sup>+</sup> catalyzed hydration of an alkyne??
A)an alcohol
B)an enol
C)a 1,2-diene
D)an epoxide
Q4) Consider an unknown with the molecular formula C<sub>4</sub>H<sub>6</sub>.
The number of possible alkyne isomers is _____.
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Q1) Which of the following statements is not true about the allyl radical
A)The carbon-carbon bond lengths are identical.
B)The unpaired electron density is shared between carbons 1 and 2.
C)It undergoes reaction with bromine to give a single product.
D)It is formed by abstraction of a hydrogen atom from the methyl group of propene.
Q2) Which of the following has the list of compounds in the correct order of decreasing density (higher density > lower density)?
A)CH<sub>2</sub>Cl<sub>2</sub> > CH<sub>2</sub>Br<sub>2</sub> >
CH<sub>2</sub>I<sub>2</sub>
B)CH<sub>2</sub>Cl<sub>2</sub> > CH<sub>2</sub>I<sub>2</sub> >
CH<sub>2</sub>Br<sub>2</sub>
C)CH<sub>2</sub>I<sub>2</sub> > CH<sub>2</sub>Br<sub>2</sub> > CH<sub>2</sub>Cl<sub>2</sub>
D)CH<sub>2</sub>I<sub>2</sub> > CH<sub>2</sub>Cl<sub>2</sub> > CH<sub>2</sub>Br<sub>2</sub>
Q3) During bromination using NBS, the addition product is not observed because the rate of addition is _______than the rate of the chain propagation steps.
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Q1) Which of the following statements is true regarding the reaction of tert-butyl bromide with water?
A)the rate is proportional to the concentration of tert-butyl bromide
B)the rate is proportional to the concentration of water
C)the rate is independent of the identity of the solvent
D)the rate of the reaction is independent of the temperature
Q2) Which of the following is best set of conditions for the preparation of tert-butanol?
A)tert-butyl fluoride in water
B)tert-butyl bromide in water
C)tert-butyl fluoride and NaOH in DMSO
D)tert-butyl bromide and NaOH in DMSO
Q3) Which of the following anions is the most nucleophilic in polar protic solvents?
A)F<sup>-</sup>
B)Cl<sup>-</sup>
C)Br<sup>-</sup>
D)I<sup>-</sup>
Q4) Compound B by is formed by an _____ mechanism.
Q5) The mechanism for these reactions is _______.
Q6) The nucleophile is these reactions is________.
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Q1) Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?
A)methanol
B)ethanol
C)2-propanol
D)2-methyl-2-propanol
Q2) What is the major organic product obtained upon heating a mixture of 2-methylcyclopentanol and 85% H<sub>3</sub>PO<sub>4</sub>?
A)1-methylcyclopentene
B)3-methylcyclopentene
C)4-methylcyclopentene
D)methylenecyclopentene
Q3) (CH<sub>3</sub>)<sub>3</sub>CO<sup>- </sup>Na<sup>+ </sup> would be formed by the reaction of sodium metal and 1-butanol.
A)True
B)False
Q4) The mechanism of this reaction would be classified as ______.
Q5) Provide the complete IUPAC name for the starting material in this reaction.
Q6) _______Oxidation of a secondary alcohol to a ketone.
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Q1) What type of mechanism accounts for the cleavage of tert-butyl methyl ether upon treatment with HBr?
A)S<sub>N</sub>1
B)S<sub>N</sub>2
C)E1
D)E2
Q2) Which of the following statements is not true?
A)Crown ethers complex alkali metal ions by donation of lone pairs from the oxygen atoms to the metal cation.
B)Metal ion complexes of crown ethers dissolve in nonpolar aprotic organic solvents
C)Addition of 18-crown-6 to a solution of benzyl bromide and potassium cyanide in a nonpolar solvent increases the rate of nucleophilic substitution.
D)18-Crown-6 is a planar molecule
Q3) A crown ether named 18-crown-6 has a total of carbons and oxygens .
Q4) The name of the product of the reaction is _______________________.
Q5) When cyclopentene is treated with peroxyacetic acid, the product that forms is
Q6) The reaction shown here proceeds by a(n) _______ mechanism.
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Q1) he amount of energy in infrared light corresponds to the amount of energy needed to increase certain molecular motions, such as bond vibrations, in organic molecules.
A)True
B)False
Q2) Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the highest energy?
A)radio waves
B)ultraviolet
C)infrared
D)visible
Q3) Cyclohexene and 2-hexyne both have the molecular formula C<sub>6</sub>H<sub>10</sub>. Any of the following regions of an IR spectrum could be used to distinguish these two compounds.
3020-3100 cm<sup>-</sup><sup>1</sup> 2100-2260 cm<sup>-</sup><sup>1</sup> 1650-1670 cm<sup>-</sup><sup>1</sup>
A)True
B)False
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Q1) How many sets of equivalent protons are there in 3-methylhexane?
A)2
B)3
C)6
D)7
Q2) What is the splitting of the signal in the <sup>1</sup>H NMR spectrum for the methyl protons of propane?
A)singlet
B)doublet
C)triplet
D)quartet
Q3) The calibration standard for <sup>1</sup>H and <sup>13</sup>C NMR is _____.
A)TMS
B)high-field or upfield side
C)MHz
D)delta (\(\delta\))
E)low-field or downfield side
F)chemical shift
G)intensity
Q4) ______ 1

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Q1) How many carbon atoms are present in a molecule which gives an M+1 peak that is 5.74% of the intensity of the molecular ion?
A)5
B)6
C)11
D)12
Q2) Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 43?
A)1-hexanol
B)2-hexanol
C)hexanal
D)hexanoic acid
Q3) Which of the following gives rise to a prominent M - 18 peak in the mass spectrum?
A)hexane
B)1-chloropentane
C)1-pentanol
D)3-methylpentane
Q4) The peak at a m/z of _____ represents M<sup>+</sup>.
Q5) The peak at a m/z of _____ represents the base peak.
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Q1) Substance A is termed a ___________reagent.
Q2) Which of the following is the best choice of solvent for the formation of phenyllithium by the reaction of bromobenzene with lithium?
A)water
B)ethanol
C)tetrahydrofuran
D)acetic acid
Q3) What term describes the process whereby an alkyl halide undergoes reaction with magnesium metal to give an alkylmagnesium bromide (Grignard reagent)?
A)nucleophilic substitution
B)electrophilic addition
C)oxidative addition
D)reductive elimination
Q4) Which of the following is not true regarding the carbon atom of the methylene carbene, H<sub>2</sub>C: ?
A)it is sp<sup>2</sup> hybridized
B)it has a complete octet of valence electrons
C)it has a vacant 2p atomic orbital
D)it has a lone pair of electrons in an sp<sup>2</sup> molecular orbital
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Q1) Which of the following is not true about the Wittig reaction?
A)triphenylphosphine reacts with 2<sup>\(\circ\)</sup> alkyl bromides by an S<sub>N</sub>2 reaction to give an alkyltriphenylphosphonium bromide
B)alkyltriphenylphosphonium bromides are deprotonated by strong bases to give a phosphonium ylide
C)phosphonium ylids are nucleophilic
D)the product of the Wittig reaction is an alkyne
Q2) Which of the following is a reactive intermediate in the reaction of acetone with bromine in acetic acid to form 1-bromo-2-propanone?
A)carbanion
B)enol
C)enolate
D)radical
Q3) The nucleophile in this reaction is _____.
A)A
B)B

Q4) The product of this reaction is called a(n)___________.
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Q1) Which of the following has the highest boiling point?
A)acetic acid
B)pentanol
C)butanoic acid
D)pentanal
Q2) Ethyl propanoate (CH<sub>3</sub>CH<sub>2</sub>COOCH<sub>2</sub>CH<sub>3</sub>) can be prepared by the reaction of ethanol with ____________ acid.
Q3) Which of the following best describes the key mechanistic steps in the esterification of a carboxylic acid upon treatment with an alcohol in the presence of a strong acid?
A)addition followed by elimination
B)substitution followed by addition
C)elimination followed by addition
D)addition followed by decarboxylation
Q4) When CO<sub>2</sub> is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced.
Q5) The benzyl alcohol will be recovered from the _______ layer.
Q6) The 2-hydroxybenzoic acid will be recovered from the _______ layer.
Q7) The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer.
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Q1) An anhydride is represented by the structure numbered ____.
Q2) Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?
A)esters > amides > acid chlorides
B)amides > acid chlorides > esters
C)acid chlorides > esters > amides
D)esters > acid chlorides > amides
Q3) Both amides and nitriles are acyl derivatives of carboxylic acids.
A)True
B)False
Q4) Which of the following can be made by acid-promoted hydrolysis of a nitrile?
1)an acid
2)an alcohol
3)an imine
4)an imide
A)only 1
B)only 1 and 2
C)only 2 and 3
D)only 4
Q5) The substance that is classified as an anhydride is _____.
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Q1) Consider the steps in the mechanism for a base catalyzed aldol condensation. The _______ step in the base catalyzed aldol condensation is addition of an enolate to a carbonyl group.
Q2) How many different aldols (\(\beta\)-hydroxyaldehydes), including constitutional isomers and stereoisomers, are formed upon treatment of butanal with base?
A)1
B)2
C)3
D)4
Q3) How many different \(\beta\)-hydroxyaldehydes and \(\beta\)-hydroxyketones, including constitutional isomers and stereoisomers, are formed upon treatment of a mixture of acetone and benzaldehyde with base?
A)1
B)2 C)3
D)4
Q4) A 1,6-diester will produce a five-membered ring via a Dieckmann cyclization.
A)True
B)False
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Q1) The nucleophile in this reaction is ____.
A)A
B)B
C)C
D)D
Q2) The electrophile in this reaction is ____.
A)A
B)B
C)C
D)D
Q3) Which of 1,3-cyclohexadiene and 1,4-cyclohexadiene has the greatest heat of hydrogenation (i.e., the most exothermic reaction with H<sub>2</sub> in the presence of a catalyst). Provide a brief explanation for your choice ?
Q4) What are the units of \(\varepsilon\) in ultraviolet-visible spectroscopy?
A)M<sup>-</sup><sup>1</sup>.cm<sup>-</sup><sup>1</sup> B)M.cm
C)J.mol<sup>-</sup><sup>1</sup>.M<sup>-</sup><sup>1</sup> D)none, \(\varepsilon\) is a dimensionless quantity
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Q1) What is the approximate length of the carbon-carbon bonds in benzene?
A)110 pm
B)121 pm
C)139 pm
D)156 pm
Q2) List all of the requirements of a molecule for it to be considered aromatic.
Q3) Assuming that the sulfur atom is sp<sup>2</sup>-hybridized, there are _____ \(\pi\)-electrons in the sulfathiazole ring.
Q4) This structure contains ____ \(\pi\) electrons.
Q5) What is the hybridization of the oxygen atom of furan?
A)s
B)sp
C)sp<sup>2</sup>
D)sp<sup>3</sup>
Q6) Which orbital contains the lone pair on the nitrogen atom of pyridine?
A)s
B)p
C)sp
D)sp<sup>2</sup>
Q7) If named as an annulene, the name would be [ __ ] annulene.
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Q1) Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions?
A)CH<sub>3</sub>, OCH<sub>3</sub>, COCH<sub>3</sub>
B)Cl, CN, NO<sub>2</sub>
C)Cl, NH<sub>2</sub>, CH<sub>3</sub>
D)CH<sub>3</sub>, NH<sub>2</sub>, OCH<sub>3</sub>
Q2) What is the role of AlCl<sub>3</sub> in Friedel Crafts acylations using acid chlorides?
A)Lewis acid
B)electrophile
C)base
D)nucleophile
Q3) Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?
A)Cl, CN, NO<sub>2</sub>
B)Cl, NH<sub>2</sub>, CH<sub>3</sub>
C)CH<sub>3</sub>, OCH<sub>3</sub>, COCH<sub>3</sub>
D)CH<sub>3</sub>, NH<sub>2</sub>, OCH<sub>3</sub>
Q4) The name of product D is ________________________.
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Q1) Substance _____ is pyridine.
Q2) What is the intermediate in the Cope elimination, in which a 3<sup>\(\circ\)</sup> amine is treated with hydrogen peroxide followed by heat?
A)a tetraalkylammonium hydroxide salt
B)an amine oxide
C)a 3<sup>\(\circ\)</sup> carbocation
D)an amide anion
Q3) Which of the following amines can be prepared from an organic bromide reaction with potassium cyanide followed by reduction?
A)1-heptanamine
B)benzylamine
C)2-butanamine
D)tert-butyl amine
Q4) The reaction of a 2<sup>o</sup> amine with nitrous acid gives a nitrosamine.
A)True
B)False
Q5) Substance _____ is aniline.
Q6) Provide a line-bond structure of N-methylaniline.
Q7) Provide a line-bond structure of N,N-dimethylcyclopentanamine.
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Q1) In the Heck reaction, alkenes with large substituent groups are the most reactive.
A)True
B)False
Q2) Which of the following terms describes the mechanism of a Diels-Alder reaction?
A)electrophilic addition
B)nucleophilic addition
C)pericyclic addition
D)conjugate addition
Q3) During oxidative addition, the coordination (number) of the metal ________ by two.
Q4) ______involves an interchange of alkenyl groups.
A)Heck reaction
B)Stille coupling
C)Suzuki coupling
D)Sonogashira coupling
E)Alkene metathesis
Q5) In an alkene metathesis reaction where both alkenyl groups are in the same molecule, the product formed is a _______________.
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Q1) Structure ____ represents a aldopentose.
Q2) Which of the following is an alditol?
A)glucose
B)fructose
C)glucaric acid
D)mannitol
Q3) The anomer of ribose is drawn is _______. (alpha or beta)
Q4) The structures that represent reducing sugars are:
a. only the ketoses.
b. only the aldoses.
c. all of these structures.
Q5) A 1,4-\(\alpha\)-linkage between two glucose units produces a disaccharide called maltose.
A)True
B)False
Q6) Starch, cellulose, and surcrose are all classified as polysaccharides.
A)True
B)False
Q7) Structure ____ represents a ketohexose.
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Q8) The correct name for the cyclic structure is__________________________.

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Q1) Male sex hormones like testosterone are called _____________.
Q2) Female sex hormones like estrone are called _____________.
Q3) Which of the following is a synthetic detergent?
A)sodium 4-dodecylbenzenesulfonate
B)N-(2-hydroxyethyl)dodecanamide
C)sodium perborate dihydrate
D)sodium palmitate
Q4) What functional group of the protein opsin reacts with retinal to form rhodopsin, a light-sensitive pigment?
A)carboxylic acid
B)amide
C)1<sup>\(\circ\)</sup> amine
D)alcohol
Q5) What is the approximate value of pK<sub>a</sub> of a bile acid?
A)-4
B)1
C)5
D)25
Q6) What are the roles of LDL and HDL? Which one is "good" cholesterol, which one is bad"?
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Q1) 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
Q2) Which of the following amino acids is not chiral?
A)leucine
B)glycine
C)alanine
D)proline
Q3) Which of the following reagents can be used to cleave a benzyloxycarbonyl protecting group from a peptide?
A)HBr, CH<sub>3</sub>CO<sub>2</sub>H
B)conc. NaOH
C)heat
D)NaCl, H<sub>2</sub>O
Q4) A tetrapeptide contains the amino acids Phe, Ala, Gly, and Leu. Partial hydrolysis produces the dipeptides Phe-Ala, Ala-Gly, and Leu-Phe. The structure of the tetrapeptide is _________________________. Use the three-letter designations for the amino acids separated by dashes (-).
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Q1) What sequence is fully complementary to the following sequence?
5'-AGTCAATTC-3'
Q2) Provide the structure of cytidine 5'-monophosphate, a nucleotide consisting of a cytosine base, a ribose and a phosphate group.
Q3) Which of the following is a pyrimidine base?
A)guanine
B)adenine
C)thymine
D)triethylamine
Q4) What is the approximate distance between stacked bases in a double helix of DNA?
A)340 pm
B)800 pm
C)2000 pm
D)3400 pm
Q5) The G-C base pair is the weaker than the A-T base pair as it has two hydrogen bonds whereas the A-T base pair has three.
A)True
B)False
Q6) Provide the structure of adenosine triphosphate, ATP.
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Q1) What type of intermediate is formed in the polymerization of isobutylene with BF<sub>3</sub>/H<sub>2</sub>O?
A)carbocation
B)carbanion
C)radical
D)radical anion
Q2) Provide the structure of azoisobutyronitrile, AIBN, and show the mechanism whereby it undergoes thermal decomposition to give two radicals and a molecule of N<sub>2</sub>.
Q3) Provide the mechanism for backbiting of a radical chain end of polyethylene, which results in a butyl side chain on the polymer backbone.
Q4) Provide the structure of poly(ethylene succinate).
Q5) Which of the following relationships is not true?
A)T<sub>g</sub> < T<sub>m</sub>
B)M<sub>w</sub> \(\ge\)M<sub>n</sub>
C)polydispersity index \(\le\) 1
D)M<sub>n</sub> = (average degree of polymerization, n) * (molecular weight of repeat unit)
Q6) Provide the structure of polystyrene.
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