Organic Chemistry I Exam Materials
Course Introduction
Organic Chemistry I is an introductory course that explores the fundamental principles of carbon-based compounds. The course covers the structure, bonding, and properties of organic molecules, with emphasis on alkanes, alkenes, alkynes, and aromatic compounds. Students learn about functional groups, nomenclature, stereochemistry, and reaction mechanisms, including substitution and elimination reactions. Through lectures, laboratory experiments, and problem-solving exercises, the course builds a foundation for understanding how organic molecules are synthesized, analyzed, and applied in biological and industrial contexts.
Recommended Textbook
Organic Chemistry 4th Edition by Janice Gorzynski
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Page 2
Chapter 1: Structure and Bonding
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Q1) Which of the following compounds are non-polar? \[\begin{array} { c c c c }
\mathrm { CO } _ { 2 } & \mathrm { NH } _ { 3 } & \mathrm { H } _ { 2 } \mathrm { O } &
\mathrm { BCl } _ { 3 } \\
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}\]
A) I, IV
B) I, II
C) II, III
D) II, IV
Answer: A
Q2) Which compound contains the most polar bond? \(\mathrm { CH } _ { 3 }\) \(\begin{array} { c c } \mathrm { CH } _ { 3 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { Cl } \end{array}\)\(\mathrm { CH } _ { 3 } \mathrm { NH } _ { 2 }\) I\(\quad\quad\quad\quad\)II\(\quad\quad\quad\)III\(\quad\quad\quad\)IV
A) I
B) II
C) III
D) IV
Answer: B
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Chapter 2: Acids and Bases
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Q1) Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH<sub>3</sub>OH
B) H<sub>2</sub>O
C) CH<sub>3</sub>COOH
D) BF<sub>3</sub>
Answer: D
Q2) Which of the following is the strongest base?
A) CH<sub>3</sub>COCH<sub>3</sub>
B) CH<sub>3</sub>COOH
C) NH<sub>3</sub>
D) H<sub>2</sub>O
Answer: C
Q3) Which of the following species is the conjugate base of methanol, CH<sub>3</sub>OH?
A) CH<sub>3</sub>OH<sub>2</sub><sup>+</sup>
B) CH<sub>3</sub>O<sup>-</sup>
C) CH<sub>3</sub><sup>-</sup>
D) CH<sub>4</sub>
Answer: B
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Page 4
Chapter 3: Introduction to Organic Molecules and Functional Groups
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Q1) Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?
A) The larger the surface area, the weaker the intermolecular force.
B) The larger the surface area, the stronger the intermolecular forces.
C) The smaller the surface area, the stronger the intermolecular forces.
D) There is no relationship between surface area and intermolecular forces.
Answer: B
Q2) Why do \(\pi\) bonds confer reactivity on a particular molecule?
A) Because \(\pi\) bonds are difficult to break in chemical reactions.
B) Because \(\pi\) bonds make a molecule an acid.
C) Because \(\pi\) bonds are easily broken in chemical reactions.
D) Because \(\pi\) bonds make a molecule an electrophile.
Answer: C
Q3) Why do heteroatoms confer reactivity on a particular molecule?
A) Because they have lone pairs and create electron-rich sites on carbon.
B) Because they have lone pairs and create electron-deficient sites on carbon.
C) Because they are electronegative and act as electrophiles.
D) Because they are electropositive and act as nucleophiles.
Answer: B
Page 5
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Chapter 4: Alkanes
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Q1) Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane
B) Cyclohexane
C) Cyclopentane
D) Cycloheptane
Q2) Which of the following statements about alkanes is true?
A) Alkanes are aliphatic hydrocarbons having only C-C and C-H \(\pi\) bonds.
B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons.
C) Acyclic alkanes contain carbons joined in one or more rings.
D) Acyclic alkanes have general molecular formula C<sub>n</sub>H<sub>2n</sub>.
Q3) Which of the following statements about the conformations of acyclic alkanes is not true?
A) The staggered and eclipsed conformations are equally stable.
B) The staggered conformations are more stable than the eclipsed conformations.
C) An energy minimum and maximum occur every 60° as the conformation changes from staggered to eclipsed.
D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
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6
Chapter 5: Stereochemistry
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Q1) A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°. What is the specific rotation of the S enantiomer?
A) +50°
B) -40°
C) +40°
D) -50°
Q2) What is the main carbohydrate in the seeds and roots of plants?
A) Starch
B) Glucose
C) Cellulose
D) Glycogen
Q3) Which of the following statements is true?
A) Achiral molecules usually contain a plane of symmetry.
B) With one tetrahedral stereogenic center, a molecule may or may not be chiral.
C) With two or more stereogenic centers, a molecule is always chiral.
D) Chiral molecules usually contain a plane of symmetry.
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Chapter 6: Understanding Organic Reactions
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Q1) Which of the following statements about bond breaking is true?
A) Homolysis and heterolysis require energy.
B) In homolysis, the electrons in the bond are divided unequally.
C) In heterolysis, the electrons in the bond are divided equally.
D) Homolysis generates charged intermediates.
Q2) Which of the following statements is true?
A) The product is favored in reaction in which \(\Delta\)H° is a positive value.
B) Entropy decreases when an acyclic compound forms a ring.
C) In homolytic bond cleavage, entropy decreases and favors formation of products.
D) The starting material is favored in a reaction in which \(\Delta\)H° is a negative value.
Q3) Which of the following statements about elimination reactions is true?
A) Two \(\sigma\) bonds are broken.
B) Two \(\sigma\) bonds are formed.
C) Two \(\pi\) bonds are broken.
D) Two \(\pi\) bonds are formed.
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Chapter 7: Alkyl Halides and Nucleophilic Substitution
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Q1) Which of the following statements is true?
A) All good leaving groups are strong bases with weak conjugate acids.
B) Left-to-right across a row of the periodic table, leaving group ability decreases.
C) Down a column of the periodic table, leaving group ability decreases.
D) The conjugate bases of strong acids are good leaving groups.
Q2) What is the rate-determining step of an S<sub>N</sub>1 reaction mechanism?
A) Reaction of the nucleophile with the carbocation to form the product.
B) Breaking the bond between the carbon and the leaving group to generate a carbocation.
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon.
D) None of the above.
Q3) Which of the following statements about an S<sub>N</sub>1 reaction mechanism is true?
A) The reaction is fastest with primary alkyl halide.
B) The reaction exhibits a one-step mechanism.
C) The reaction rate increases as the leaving group ability increases.
D) The reaction rate increases as the strength of the nucleophile increases.
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Chapter 8: Alkyl Halides and Elimination Reactions
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Q1) Which of the following represents the rate law for an E2 reaction?
A) Rate = k[alkyl halide]
B) Rate = k[alkyl halide][base]
C) Rate = k[alkyl halide]<sup>2</sup>
D) Rate = k[base]<sup>2</sup>
Q2) What is the major elimination product in the reaction of 1-bromobutane with potassium tert-butoxide in tert-butanol?
A) cis-2-Butene
B) 1-Butene
C) trans-2-Butene
D) Butanol
Q3) How many different E2 products can form from the dehydrohalogenation of 2-bromobutane?
A) 1
B) 2
C) 3
D) 4
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10
Chapter 9: Alcohols, Ethers and Epoxides
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Q1) Which of the following statements about a crown ether-cation complex is not true?
A) It is a host-guest complex.
B) The crown ether is the guest and the cation is the host.
C) The crown ether is the host and the cation is the guest.
D) The host-guest complex is soluble in nonpolar solvents.
Q2) Which of the following statements about carbocation rearrangement is not true?
A) A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom.
B) A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group.
C) 1,2-Shifts convert a less stable carbocation to a more stable carbocation.
D) The migrating group in a 1,2-shift moves with one bonding electron.
Q3) What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI?
A) tert-Butyl alcohol and iodomethane
B) tert-Butyl iodide and iodomethane
C) tert-Butyl alcohol and methanol
D) tert-Butyl iodide and methanol
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11
Chapter 10: Alkenes
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Q1) Markovnikov addition of HBr to CH<sub>3</sub>CH=CH<sub>2</sub> involves which of the following?
A) Initial attack by bromide anion (Br<sup>-</sup>).
B) Initial attack by bromine radical (Br ).
C) Formation of a primary carbocation.
D) Formation of a secondary carbocation.
Q2) Which of the following statements about hydroboration/oxidation of alkenes is true?
A) In hydroboration, the boron atom bonds to the more substituted carbon.
B) Hydroboration occurs with anti addition.
C) Oxidation occurs with retention of configuration.
D) 9-BBN does not undergo hydroboration in the same manner as BH<sub>3</sub>.
Q3) Calculate the degree of unsaturation for a molecule with molecular formula C<sub>6</sub>H<sub>11</sub>Cl.
A) 1
B) 2
C) 3
D) 0
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Page 12
Chapter 11: Alkynes
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Q1) Which of the following bases cannot deprotonate acetylene? You are given the pK<sub>a</sub> values of the conjugate acids in parentheses. \(\mathrm { CH } _ { 3 } \mathrm { NH } ^ { - } \left( \mathrm { p } K _ { a } = 40 \right) \quad \mathrm { CO } _ { 3 } ^ { 2 - } \left( \mathrm { p } K _ { a } = 10.2 \right) \quad \mathrm { CH } _ { 2 }
= \mathrm { CH } ^ { - } \left( \mathrm { p } K _ { a } = 44 \right) \quad \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CO } ^ { - } \left( \mathrm { p } K _ { a } = 18 \right)\)
I\(\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\)II\(\quad \quad\quad\quad\quad\quad\quad\quad\quad\)III\(\quad\quad\quad\quad\q uad\quad\quad\quad\quad\quad\quad\)IV
A) Only I and II
B) Only I and III
C) Only II and III
D) Only II and IV
Q2) How many \(\sigma\) bonds and \(\pi\) bonds are present in a triple bond?
A) One \(\sigma\) bond and one \(\pi\) bond.
B) One \(\sigma\) bond and two \(\pi\) bonds.
C) Two \(\sigma\) bonds and one \(\pi\) bond.
D) Two \(\sigma\) bonds and two \(\pi\) bonds.
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Page 13
Chapter 12: Oxidation and Reduction
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Q1) Which of the following classes of organic compounds cannot undergo reduction easily?
A) Alkanes
B) Alkenes
C) Alkynes
D) Carboxylic acids
Q2) Which of the following statements about oxidation and reduction is not true?
A) The conversion of an alkyne to an alkene is reduction.
B) The conversion of an alkene to an alkane is reduction.
C) Oxidation results in a decrease in the number of C-H bonds.
D) Reduction results in an increase in the number of C-Z bonds.
Q3) What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH<sub>3</sub>Cl + 2Li \(\to\) CH<sub>3</sub>Li + LiCl
A) Oxidized
B) Reduced
C) Oxidized and Reduced
D) Neither oxidized nor reduced
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14
Chapter 13: Mass Spectrometry and Infrared Spectroscopy
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Q1) What type(s) of molecular motion is (are) observed using infrared spectroscopy?
A) Stretching and bending
B) Rotation and excitation
C) Spin flipping
D) Fragmentation
Q2) What type of feature will be observed in the EI mass spectrum of chlorobenzene?
A) An absorption at 3100 cm<sup>-1</sup>
B) A signal at 113.
C) A signal at 112 and a signal at 114 in a ratio of 3:1
D) A signal at 112 and a signal at 114 in a ratio of 1:1
Q3) The functional group region of an infrared spectrum is:
A) Where the cations appear
B) Greater than or equal to 1500 cm<sup>-1</sup>
C) Less than 1500 cm<sup>-1</sup>
D) Greater than or equal to 2500 cm<sup>-1</sup>
Q4) In electron impact mass spectrometry (EIMS), what is being detected?
A) The molecular mass of the compound
B) The molecular formula of the compound
C) The mass to charge ratio of any ionic species
D) The mass to charge ratio of any neutral species
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Chapter 14: Nuclear Magnetic Resonance Spectroscopy
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Q1) What region of the electromagnetic spectrum does nuclear magnet resonance spectroscopy use?
A) Radio frequency
B) Microwave frequency
C) Infrared frequency
D) Visible frequency
E) Ultraviolet frequency
Q2) Which of the following statements about <sup>13</sup>C NMR is not true?
A) "In <sup>13</sup>C proton-decoupled NMR spectra, all peaks are singlets."
B) "<sup>13</sup>C NMR spectra display peaks for only carbons that bear hydrogen atoms."
C) "<sup>13</sup>C NMR chemical shifts occur over a greater range than <sup>1</sup>H NMR chemical shifts."
D) "<sup>13</sup>C NMR easily differentiates between the different hybridized carbons (sp<sup>3</sup>, sp<sup>2</sup> and sp hybridized carbons)."
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Chapter 15: Radical Reactions
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Q1) A possible reaction of ethane with chlorine is shown below. \[\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } + \mathrm { Cl } _ { 2 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HCl }\] This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain propagating step(s) is (are) _______. \([ 1 ] \quad \mathrm { Cl } _ { 2 } \longrightarrow 2 \mathrm { Cl } \cdot\)
[2] \(\mathrm { Cl } \cdot + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } \stackrel { \text { slow } } { \longrightarrow } \mathrm { HCl } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 }^ \cdot\)
[3] \(\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^\cdot + \mathrm { Cl } _ { 2 } \stackrel { \text { fast } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { Cl }\cdot\).
A) Only [1] and [2]
B) Only [2] and [3]
C) Only [1] and [3]
D) Only [3]
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Chapter 16: Conjugation, Resonance, and Dienes
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Q1) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene?
A) 3-Bromo-1-butene
B) 1-Bromo-2-butene
C) 2-Bromo-2-butene
D) 2-Bromo-1-butene
Q2) Which of the following statements about resonance structures is true?
A) The placement of atoms is different.
B) The placement of \(\pi\) bonds is different.
C) The placement of \(\sigma\) bonds is different.
D) The placement of nonbonded electrons is the same.
Q3) Which of the following is the appropriate term for the mechanism of the addition of HBr to 1,3-dienes?
A) Nucleophilic addition
B) Electrophilic addition
C) Free radical addition
D) Conjugate addition
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18
Chapter 17: Benzene and Aromatic Compounds
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Q1) Which of the following statements about the structure of benzene is not true?
A) Benzene is planar.
B) Benzene has three short double bonds alternating with three longer single bonds.
C) The electrons in the pi bonds are delocalized around the ring.
D) Benzene has six pi electrons.
Q2) Which of the following statements about benzene is true?
A) Benzene is a saturated hydrocarbon.
B) Benzene undergoes addition reactions.
C) Benzene has five degrees of unsaturation.
D) Benzene undergoes substitution reactions.
Q3) Which of the following is not one of the Hückel's criteria for aromaticity?
A) The molecule must be cyclic.
B) The molecule must be planar.
C) The molecule must be completely conjugated.
D) The molecule must have 4n pi electrons.
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Chapter 18: Electrophilic Aromatic Substitution
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Q1) Which of the following substituents is a meta director?
A) "- N(CH<sub>3</sub>)<sub>2</sub>"
B) "- OCH<sub>3</sub>"
C) "- NHCOCH<sub>3</sub>"
D) "- SO<sub>3</sub>H"
Q2) What are the two distinct pathways for nucleophilic aromatic substitution?
A) Addition-substitution and substitution-addition
B) Addition-elimination and elimination-addition
C) Addition-addition and elimination-elimination
D) Elimination-substitution and substitution-elimination
Q3) What is a major problem with Friedel-Crafts alkylation?
A) It requires high temperatures.
B) The conditions are too acidic.
C) The starting material is frequently over-alkylated.
D) The products coordinate with the aluminum chloride.
Q4) What is the electrophile in aromatic nitration?
A) NO<sup>+</sup>
B) NO<sub>2</sub><sup>+</sup>
C) NO<sub>3</sub><sup>+</sup>
D) NO<sub>2</sub>H
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Chapter 19: Carboxylic Acids and the Acidity of the O-H
Bond
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Q1) Which of the following bases are strong enough to significantly deprotonate ethanol, CH<sub>3</sub>CH<sub>2</sub>OH (pKa = 16)?
A) NaOCH<sub>3</sub>
B) NaOH
C) NaH
D) NaOCH<sub>2</sub>CH<sub>3</sub>
Q2) Why is pure acetic acid often called glacial acetic acid?
A) Because it freezes just below 0°C, forming white crystals.
B) Because it freezes just below 100°C, forming white crystals.
C) Because it freezes just below room temperature, forming white crystals.
D) Because it freezes just above room temperature, forming white crystals.
Q3) What two groups make up the carboxylic acid group (RCOOH)?
A) Carbon dioxide and hydrogen
B) Carbonyl and hydroxyl
C) Carbon monoxide and hydroxyl
D) Carbonyl oxide and hydrogen
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Chapter 20: Introduction to Carbonyl Chemistry;
Organometallic Reagents; Oxidation and Reduction
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Q1) Which reagent can be used to reduce the alkene in cyclopentenone?
A) NaBH<sub>4</sub>
B) LiAlH<sub>4</sub>
C) H<sub>2</sub> and Pd-C
D) DIBAL-H
Q2) What is the name of the general reaction type that carboxylic acids, esters, and amides undergo?
A) Electrophilic acyl addition
B) Nucleophilic acyl addition
C) Nucleophilic acyl substitution
D) Electrophilic acyl substitution
Q3) What are the two steps in a nucleophilic addition mechanism?
A) Nucleophilic attack followed by protonation.
B) Nucleophilic attack followed by deprotonation.
C) Nucleophilic attack followed by substitution.
D) Nucleophilic attack followed by elimination.
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Chapter 21: Aldehydes and Ketones Nucleophilic Addition
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Q1) What is the first step in nucleophilic addition under acidic conditions?
A) Protonation of the nucleophile
B) Addition of the nucleophile
C) Loss of water
D) Protonation of the carbonyl
Q2) What is the driving force for the Wittig reaction?
A) The formation of an alkene
B) The deprotonation of a phosphonium salt
C) The elimination of triphenylphosphine oxide
D) The formation of a phosphonium salt
Q3) Identify how you could synthesize an enamine.
A) React a ketone or an aldehyde with a secondary amine.
B) React a ketone or an aldehyde with a primary amine.
C) React a ylide with a primary amine.
D) React a ylide with a secondary amine.
Q4) Which of the following statements about carbohydrates is not true?
A) Carbohydrates are sugars and starches.
B) Carbohydrates often contain acetals and hemiacetals.
C) In solution, glucose is in the cyclic acetal form only.
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.
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Chapter 22: Carboxylic Acids and Derivatives
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Q1) Where do the carbonyl signals appear in the <sup>13</sup>C NMR spectrum of carboxylic acid derivatives?
A) 1700 cm<sup>-1</sup>
B) 180-160 ppm
C) 2.5-3.0 ppm
D) 100-80 ppm
Q2) n-Butanenitrile will undergo all of the following listed reactions except one. Which reaction listed is not true for n-butanenitrile?
A) n-Butane nitrile will react with ethylmagnesium bromide to form an alcohol.
B) n-Butanenitrile with be reduced to butyl amine in the presence of LiAlH<sub>4</sub> with an aqueous work-up.
C) n-Butanenitrile is hydrolyzed in the presence of acid to form butanoic acid.
D) n-Butanenitrile is reduced with DIBAL-H to form n-butanal.
Q3) Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?
A) Nitrogen is a better leaving group.
B) Chloride is a better leaving group.
C) Nitrogen donates more electron density into the carbonyl.
D) The amide anion is less basic.
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Chapter 23: Substitution Reactions of Carbonyl
Compounds at the Alpha-Carbon
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Q1) Which of the following is the intermediate for halogenation of ketones under acidic conditions?
A) An enolate
B) An enol
C) A tautomer
D) An epimer
Q2) Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?
A) Yes
B) No
Q3) For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound. This is due largely to what?
A) The C=O bond is much stronger than the C=C bond.
B) The C=C bond is much stronger than the C=O bond.
C) The keto form can undergo intramolecular hydrogen bonding.
D) The enol form can undergo intramolecular hydrogen bonding.
Q4) Will acetone be completely deprotonated by potassium tert-butoxide?
A) Yes
B) No
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Chapter 24: Carbonyl Condensation Reactions
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Q1) What reaction type is an Aldol reaction?
A) nucleophilic substitution
B) electrophilic substitution
C) electrophilic addition
D) nucleophilic addition
Q2) There are several variations of the Aldol reaction. Which of the following types of reactants leads to only one possible product with the Aldol condensation reaction?
A) Two different aldehydes with \(\alpha\)-hydrogens are able to form a single aldol condensation product.
B) Two different ketones with \(\alpha\)-hydrogens are able to form a single aldol condensation product.
C) Any aldehyde and ketone mixed together can react to form a single condensation product.
D) Any pair of aldehyde or ketone reactants where one of the reactants has no \(\alpha\)-hydrogens will lead to a single aldol product.
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Chapter 25: Amines
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Q1) Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored. Why is that?
A) Because four bonds are needed to define a stereogenic center.
B) Because chirality only exists with the tetrahedral carbon atoms.
C) Because there is usually slow interconversion between the two isomeric forms at room temperature.
D) Because there is usually rapid interconversion between the two isomeric forms at room temperature.
Q2) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?
A) Because there is rapid interconversion between the two isomeric forms at room temperature.
B) Because interconversion cannot occur between the two isomeric forms at room temperature.
C) Because the compound would be a meso compound.
D) Because the compound would be a racemic mixture.
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Chapter 26: Carbon-Carbon Bond Forming Reactions in Organic Synthesis
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Q1) Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"?
A) The reaction of a specific stereoisomer with the R<sub>2</sub>CuLi reagent will yield that particular stereoisomer as the product.
B) The reaction of a vinyl halide with the R<sub>2</sub>CuLi reagent will only yield the cis product.
C) The reaction of a vinyl halide with the R<sub>2</sub>CuLi reagent will only yield the trans product.
D) The reaction of a vinyl halide with the R<sub>2</sub>CuLi reagent will only yield one enantiomer product-either R or S configuration.
Q2) Which of the reactions listed below is not stereospecific?
A) Suzuki reaction
B) organocuprate coupling reaction
C) Heck reaction
D) Simmons-Smith reaction
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Chapter 27: Pericyclic Reactions
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Q1) Which of the following statements about a \(\pi\)* antibonding molecular orbital is true?
A) A \(\pi\)* antibonding molecular orbital is formed when two p orbitals of similar phase overlap.
B) A \(\pi\)* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap.
C) A \(\pi\)* antibonding molecular orbital is a higher-energy molecular orbital than a \(\pi\) bonding molecular orbital.
D) Both the statements "a \(\pi\)* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap" and "a \(\pi\)* antibonding molecular orbital is a higher-energy molecular orbital than a \(\pi\) bonding molecular orbital" are true.
Q2) How many bonding molecular orbitals are present in 1,3,5-hexatriene?
A) 3
B) 4
C) 5
D) 6
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Chapter 28: Carbohydrates
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Q1) Upon hydrolysis of amylopectin, what sugar is formed?
A) sucrose
B) maltose
C) lactose
D) glucose
Q2) Oxidation of a D-hexose with nitric acid forms an optically active aldaric acid. A Wohl degradation of the same D-hexose followed by oxidation with nitric acid forms an optically active aldaric acid. What are the three possible D-hexoses that fit this data?
A) D-allose, D-altrose and D-glucose
B) D-glucose, D- mannose and D-talose
C) D-glucose, D-idose and D-altrose
D) D-galactose, D-talose and D-mannose
Q3) Which of the following best describes the relationship between D-glucose and D-fructose?
A) enantiomers
B) epimers
C) anomers
D) constitutional isomers
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Chapter 29: Amino Acids and Proteins
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Q1) Which of the following is the major advantage of the Merrifield synthesis of peptides?
A) It allows for the formation of absolutely no by-products.
B) Impurities can be easily washed away.
C) Excess reagent can be used.
D) It prevents hydrogenation.
Q2) What is the separation of a racemic mixture into its component enantiomers called?
A) diastereomers
B) meso
C) resolution
D) neutralization
Q3) What are the basic steps in the Merrifield peptide synthesis?
A) coupling and hydrolysis
B) hydrolysis and deprotection
C) deprotection and hydrogenation
D) coupling and deprotection
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Chapter 30: Lipids
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Q1) What is the purpose of vitamin K?
A) energy storage
B) blood clotting
C) photosynthesis
D) hydrogenation
Q2) Which of the following correctly describes waxes?
A) long chain alcohols
B) long chain esters
C) long chain ethers
D) long chain fatty acids
Q3) What chemical process causes an oil (such as soybean oil) to become rancid?
A) hydrogenation with hydrogen
B) hydration with water
C) oxidation with molecular oxygen
D) bromination with bromine
Q4) Which of the following fatty acids has the lowest melting point?
A) palmitic acid
B) arachidic acid
C) stearic acid
D) lauric acid
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Chapter 31: Synthetic Polymers
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Q1) What is the name given to polymers with two or more different monomers?
A) homopolymers
B) copolymers
C) block polymers
D) random polymers
Q2) In which type of polymer are the chains packed less tightly together, resulting in lower melting points and a softer texture?
A) isotactic polymers
B) syndiotactic polymers
C) atactic polymers
D) cross-linked polymers
Q3) Which of the following initiators is used to make isotactic polypropylene?
A) benzoyl peroxide
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Li
C) BF<sub>3</sub>
D) Al(CH<sub>2</sub>CH<sub>3</sub>)<sub>3</sub>, TiCl<sub>4</sub>
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