Advanced Organic Chemistry
Midterm Exam
Course Introduction
Advanced Organic Chemistry delves into the intricate mechanisms, reactivity patterns, and synthetic strategies of organic molecules. Building upon fundamental principles, the course explores topics such as stereochemistry, pericyclic reactions, reactive intermediates, and the use of spectroscopic methods for structure elucidation. Students engage with contemporary research examples and advanced problem-solving, gaining a deep understanding of topics like organometallic reagents, asymmetric synthesis, and complex reaction pathways. The course emphasizes the development of critical thinking skills and the ability to design and analyze multi-step syntheses, preparing students for research or professional work in organic chemistry and related fields.
Recommended Textbook
Organic Chemistry 4th Edition by Janice Gorzynski
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Chapter 1: Structure and Bonding
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Q1) Which atomic orbitals overlap to form the C-H \(\sigma\) bonding molecular orbitals of ethane, CH<sub>3</sub>CH<sub>3</sub>?
A) Csp<sup>2</sup> + H1s
B) Csp<sup>3</sup> + H1s
C) C2p + H1s
D) Csp + H1s
Answer: B
Q2) Which of the following molecules has nonpolar covalent bonds?
A) HCl
B) N<sub>2</sub>
C) CHCl<sub>3</sub>
D) NO
Answer: B
Q3) Which molecule has the greatest difference in electronegativity (\(\Delta\)E) between the two different elements?
A) CO<sub>2</sub>
B) H<sub>2</sub>S
C) NH<sub>3</sub>
D) H<sub>2</sub>O
Answer: D
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Chapter 2: Acids and Bases
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Q1) Rank the following compounds in order of decreasing acidity, putting the most acidic first. \[\begin{array} { c c c c }
\mathrm { CH } _ { 4 } & \mathrm { NH } _ { 3 } & \text { HF } & \mathrm { H } _ { 2 }
\mathrm { O } \\
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}\]
A) IV > II > III > I
B) III > II > IV > I
C) I > II > IV > III
D) III > IV > II > I
Answer: D
Q2) Which of the following compounds is the weakest acid?
A) H<sub>2</sub>S
B) PH<sub>3</sub>
C) HCl
D) SiH<sub>4</sub>
Answer: D
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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) Which of the following lists contains common heteroatoms found in organic molecules?
A) N, O, S, P, Cl
B) Na, O, S, P, Cl
C) Na, Mg, S, N, Cl
D) Na, Mg, O, N, Cl
Answer: A
Q3) What intermolecular force is generally considered the weakest?
A) Hydrogen bonding
B) London dispersion forces
C) Dipole-dipole
D) Ion-ion
Answer: B
Page 5
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Chapter 4: Alkanes
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Q1) Which of the following compounds has only primary, secondary and quaternary carbon atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane
Q2) Which of the following compounds has primary, secondary, tertiary and quaternary carbon atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane
Q3) Which of the following compounds has primary, secondary and tertiary hydrogen atoms?
A) Pentane
B) Hexane
C) 2-Methylpentane
D) 2,2-Dimethylpentane
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6
Chapter 5: Stereochemistry
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Q1) How many chiral stereoisomers can be drawn for dimethycyclopropane?
A) 1
B) 2
C) 3
D) 4
Q2) How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane?
A) 2
B) 3
C) 4
D) 6
Q3) How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
A) 3
B) 4
C) 5
D) 6
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Page 7
Chapter 6: Understanding Organic Reactions
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Q1) Which of the following statements about equilibrium is true?
A) Equilibrium favors the products when the energy of the products is higher than the energy of the reactants.
B) Equilibrium favors the reactants when the energy of the product is lower than the energy of the reactants.
C) Equilibrium favors the products when they are less stable than the starting material of a reaction
D) Equilibrium favors the products when they are more stable than the starting material of a reaction.
Q2) Which of the following statements about substitution reactions is true?
A) Substitution reactions involve \(\pi\) bonds.
B) Substitution reactions involve \(\sigma\) bonds.
C) One \(\sigma\) bond breaks and another forms at a different carbon atom.
D) One \(\pi\) bond breaks and another forms at the same carbon atom.
Q3) Which of the K<sub>eq</sub> corresponds to the lowest value of \(\Delta\)G°?
A) "K<sub>eq </sub>= 10<sup>-3</sup>"
B) "K<sub>eq</sub> = 10<sup>-2</sup>"
C) "K<sub>eq</sub> = 10<sup>-1</sup>"
D) "\(\Delta\)G° cannot be determined"
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Page 8
Chapter 7: Alkyl Halides and Nucleophilic Substitution
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Sample Questions
Q1) Which of the following is the most nucleophilic?
A) CH<sub>4</sub>
B) H<sub>2</sub>O
C) NH<sub>3</sub>
D) HF
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 involves two steps and occurs fastest with primary alkyl halides.
B) The reaction involves one step and occurs fastest with primary alkyl halides.
C) The reaction involves one step and occurs fastest with tertiary alkyl halides.
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.
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Page 9
Chapter 8: Alkyl Halides and Elimination Reactions
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Q1) Which of the following statements about an E1 mechanism is not true?
A) The reaction is fastest with tertiary alkyl halides.
B) A better leaving group makes the reaction rate increase.
C) The reaction follows first-order kinetics.
D) Stronger bases favor the E1 reaction.
Q2) Consider the following E2 reaction. What rate equation would be observed for this reaction? \[\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \stackrel { \oplus \ominus } { \mathrm { KOC } } \left( \mathrm { CH } _ { 2 } \right) _ { 3 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } = \mathrm { CH } _ { 2 } + \mathrm { KBr } ^ { + }\]
A) Rate = k[CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br]
B) Rate =
k[CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br][KOC(CH<sub>3</sub>)<sub>3</ sub>]
C) Rate =
k[CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br][KOC(CH<sub>3</sub>)<sub>3</ sub>]<sup>2</sup>
D) Rate =
k[CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br]<sup>2</sup>[KOC(CH<sub>3</s ub>)<sub>3</sub>]
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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) What is the IUPAC of the following compound?
(CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>COH
A) 2-Ethyl-2-pentanol
B) 2-Ethyl-3-pentanol
C) 3-Ethyl-3-pentanol
D) 2,2-Diethyl-1-butanol
Q3) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?
A) Bromobenzene and sodium methoxide.
B) Phenol and sodium methoxide.
C) Bromobenzene and bromomethane.
D) Sodium phenoxide and bromomethane.
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Chapter 10: Alkenes
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Q1) What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane?
A) Carbanion
B) Carbocation
C) Cyclic bromonium ion
D) Radical
Q2) In which of the following alkene addition reactions will carbocation rearrangements occur?
A) Addition of Br<sub>2</sub> and H<sub>2</sub>O
B) Addition of Br<sub>2</sub>
C) Addition of Cl<sub>2</sub> and H<sub>2</sub>O
D) Addition of H<sub>2</sub>O in the presence of H<sub>2</sub>SO<sub>4</sub>
Q3) Which of the following reactions of alkenes takes place with anti stereochemistry only?
A) Addition of HBr
B) Addition of H<sub>2</sub>O in the presence of H<sub>2</sub>SO<sub>4</sub>
C) Addition of BH<sub>3</sub> followed by H<sub>2</sub>O<sub>2</sub>/HO<sup>-</sup>
D) Addition of Br<sub>2</sub>
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Page 12
Chapter 11: Alkynes
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Q1) Which of the following about the physical properties of alkynes is not true?
A) Alkynes have low melting and boiling points.
B) Melting and boiling points increase as the number of carbons increases.
C) Alkynes are soluble in organic solvents.
D) Alkynes are soluble in water.
Q2) Which of the following statements about tautomers is true?
A) Tautomers differ in the position of a single bond and a hydrogen atom.
B) Tautomers differ in the position of a double bond and a carbon atom.
C) Tautomers differ in the position of a double bond and a hydrogen atom.
D) Tautomers differ in the position of a single bond and a carbon atom.
Q3) In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is:
A) The Csp-H1s bond of 1-butyne.
B) The C-C triple bond of 1-butyne.
C) The H atom in HBr.
D) The Br ion.
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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 the reduction of epoxides with LiAlH<sub>4</sub> is true?
A) The nucleophile is a hydride (H<sup>-</sup>).
B) In unsymmetrical epoxides, nucleophilic attack of H<sup>-</sup> occurs at the more substituted carbon atom.
C) The reaction follows S<sub>N</sub>1 mechanism.
D) The nucleophile, H<sup>-</sup>, is a weak nucleophile.
Q3) 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.
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Page 14
Chapter 13: Mass Spectrometry and Infrared Spectroscopy
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Q1) Compared to a C-H bond, a C-D bond will vibrate where in the infrared spectrum?
A) Higher molecular weight
B) Lower molecular weight
C) Lower wavenumbers
D) Higher wavenumbers
Q2) In a typical mass spectrum, a smaller signal is observed at a mass 1 amu higher than the molecular ion peak. Why?
A) Due to small impurities in the sample
B) Machine error
C) Because a small percentage of the compound will have a carbon that is the isotope <sup>13</sup>C instead of <sup>12</sup>C
D) Because of fragmentation
Q3) Which of the following statements about the base peak of a mass spectrum is always true?
A) The base peak corresponds to the molecular ion.
B) The base peak corresponds to the most abundant ion.
C) The base peak corresponds to the lowest m/z.
D) None of the above.
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15
Chapter 14: Nuclear Magnetic Resonance Spectroscopy
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Q1) Which of the following spectroscopy methods does not involve the interaction of organic molecules with electromagnetic radiation?
A) Nuclear Magnetic Resonance
B) Infrared spectroscopy
C) Mass spectroscopy
D) Ultraviolet spectroscopy
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) Rank the following radicals in order of decreasing stability, putting the most stable first. \(\mathrm { CH } _ { 3 } \dot { \mathrm { C } } \mathrm { H } _ { 2 }\quad\) \(\mathrm { H } _ { 2 } \mathrm { C } = \mathrm { C } \dot { \mathrm { C } } \mathrm { H } _ { 2 }\quad\) \(\mathrm { CH } _ { 3 } \dot { \mathrm { C } } \mathrm { HCH } _ { 3 }\quad\) \(\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \dot { \mathrm { C } }\) I\(\quad\quad\quad\quad\quad\quad\quad\)II\(\quad\quad\quad\quad\quad \quad\quad\)III\(\quad\quad\quad\quad\quad\)IV
A) II > IV > III > I
B) III > II > IV > I
C) IV > III > II > I
D) IV > III > I > II
Q2) How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH< sub>3</sub> with Cl<sub>2</sub> and hv?
A) 3
B) 4
C) 5
D) 6
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Page 17
Chapter 16: Conjugation, Resonance, and Dienes
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Q1) Which of the following is not a product obtained from the addition of 1 equivalent of HBr to (E)-1,3-pentadiene?
A) (E)-4-Bromo-2-pentene
B) (E)-1-Bromo-2-pentene
C) 3-Bromo-1-pentene
D) (E)-3-Bromo-2-pentene
Q2) What is the definition of a resonance structure?
A) Compounds with the same molecular formula
B) Compounds with different carbon frameworks
C) Structures that differ only in the placement of pi and nonbonding electrons
D) Structures that differ only in the location of bonds
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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Chapter 17: Benzene and Aromatic Compounds
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Q1) 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.
Q2) Which of the following is not a criterion for antiaromaticity?
A) The molecule must be cyclic.
B) The molecule must have (4n + 2) pi electrons.
C) The molecule must be planar.
D) The molecule must be completely conjugated.
Q3) 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.
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Chapter 18: Electrophilic Aromatic Substitution
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Q1) What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?
A) To neutralize the base that is present
B) To make room for the electrophile
C) To make the ring more reactive
D) To rearomatize the ring system
Q2) 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
Q3) What is the reactive intermediate formed in the elimination-addition mechanism of nucleophilic aromatic substitution?
A) Carbocation
B) Radical
C) Benzyne
D) Carbanion
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Chapter 19: Carboxylic Acids and the Acidity of the O-H Bond
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Q1) 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.
Q2) Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol?
A) The carbon in the alcohol is sp<sup>2</sup> hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol.
B) The carbon in the carboxylic acid is sp<sup>3</sup> hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid.
C) The carbon in the carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.
D) The carbon in the carboxylic acid is sp<sup>2</sup> hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.
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Page 21
Chapter 20: Introduction to Carbonyl Chemistry;
Organometallic Reagents; Oxidation and Reduction
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Q1) 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
Q2) What is the name of the general reaction type that aldehydes and ketones undergo?
A) Electrophilic addition
B) Nucleophilic addition
C) Nucleophilic substitution
D) Electrophilic substitution
Q3) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate
II) benzoylchloride
III) benzamide
A) III< I < II
B) II < I < III
C) II < III < I
D) I < III < II
Page 22
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Chapter 21: Aldehydes and Ketones Nucleophilic Addition
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Q1) When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called?
A) Hemiacetal
B) Di-ether
C) Di-alkoxy alkane
D) Acetal
Q2) Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone?
A) Because the Grignard reagent will react with the acid and be quenched.
B) Because the ketone will be protonated and thus unreactive.
C) Because the ketone will form an unreactive enol.
D) Because the Grignard reagent won't dissolve in aqueous solutions.
Q3) Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except A) aqueous acid.
B) aqueous base.
C) oxidizing reagents.
D) reducing reagents.
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23
Chapter 22: Carboxylic Acids and Derivatives
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Q1) All of the following contain sp<sup>2</sup> hybridized atoms in their functional group except
A) a carboxylic acid
B) a nitrile
C) an aldehyde
D) an anhydride
Q2) You see an absorption at 2250 cm<sup>-1</sup> in the IR spectrum of a compound. What kind of functional group is present?
A) A ketone
B) An aldehyde
C) An ester
D) A nitrile
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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24
Chapter 23: Substitution Reactions of Carbonyl
Compounds at the Alpha-Carbon
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Q1) If you want to form a thermodynamic enolate, you want to:
A) Keep the reaction as cold as possible.
B) Use an aprotic solvent such as THF.
C) Use a protic solvent such as ethanol.
D) Use a carboxylic acid.
Q2) A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with
A) bromine with acetic acid.
B) bromine and aqueous hydroxide ion.
C) THF, LDA at -78 °C followed by reaction with bromine.
D) base and methyl bromide.
Q3) Which of the following compounds is the most acidic?
A) Ethyl acetoacetate
B) 2-Butanone
C) 1-Butanol
D) 3-Pentanone
Q4) Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?
A) Yes
B) No
Page 25
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Chapter 24: Carbonyl Condensation Reactions
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Q1) What is the general name of the product of a crossed Claisen reaction between a ketone and an ester?
A) "\(\beta\)-keto ester"
B) "\(\alpha\),\(\beta\)-dicarbonyl compound"
C) "\(\gamma\)-dicarbonyl compound"
D) "\(\beta\)-dicarbonyl compound"
Q2) What is an intramolecular Claisen reaction called?
A) Michael reaction
B) Robinson reaction
C) Hoffman reaction
D) Dieckmann reaction
Q3) In a Michael reaction, what is the name given to the \(\alpha\) ,\(\beta\)-unsaturated carbonyl component?
A) Michael donor
B) Michael enolate
C) Michael nucleophile
D) Michael acceptor
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Chapter 25: Amines
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Q1) In the preparation of primary amines, how can direct nucleophilic substitution between NH<sub>3</sub> and alkyl halide be made more practical than reacting NH<sub>3</sub> and the alkyl halide in a 1:1 ratio?
A) Use a large excess of NH<sub>3</sub>.
B) Use a large excess of alkyl halide.
C) Use a limited amount of NH<sub>3</sub>.
D) Make the alkyl halide sterically hindered.
Q2) Why is direct nucleophilic substitution of an alkyl halide with NH<sub>3</sub> not a very useful method for preparing primary amines?
A) NH<sub>3</sub> is not a nucleophile.
B) Elimination will occur.
C) NH<sub>3</sub> is too bulky to act as a nucleophile.
D) Polyalkylation of the amine will result in multiple products.
Q3) What is a typical characteristic absorption in the IR spectrum of a primary amine?
A) Two N-H absorptions at 2500-2600 cm<sup>-1</sup>
B) One N-H absorption at 2500-2600 cm<sup>-1</sup>
C) Two N-H absorptions at 3300-3500 cm<sup>-1</sup>
D) One N-H absorption at 3300-3500 cm<sup>-1</sup>
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Chapter 26: Carbon-Carbon Bond Forming Reactions in Organic Synthesis
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Q1) Which of the following statements is not true about the Simmons-Smith reaction?
A) The Simmons-Smith reaction involves the formation of a free carbene.
B) The Simmons-Smith reaction uses the reagents zinc-copper couple.
C) The Simmons-Smith reaction is stereospecific.
D) The Simmons-Smith reaction involves CH<sub>2</sub>I<sub>2</sub> reacting with a copper-activated zinc reagent.
Q2) Which of the following correctly describes a reaction yielding a dichorocarbene?
A) The reaction of chloroform with KOC(CH<sub>3</sub>)<sub>3</sub>.
B) The reaction of chloroform with Zn(Cu).
C) The reaction of chloroform with (CH<sub>3</sub>)<sub>2</sub>CuLi.
D) The reaction of diazomethane with KOC(CH<sub>3</sub>)<sub>3</sub>.
Q3) Why is the Grubbs catalyst synthetically important?
A) Because it only requires dilute concentrations of the reactants.
B) Because it produces only stereospecific products.
C) Because it produces only stereoselective products.
D) Because it provides a synthetic pathway for ring-closing metathesis reactions.
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Chapter 27: Pericyclic Reactions
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Q1) Which of the following statements about [2+2] cycloaddition reactions between two alkenes is true?
A) The reaction is initiated by heat.
B) The reaction is initiated by light.
C) The product is a cyclopentane derivative.
D) Each reactant contains two \(\sigma\) electrons that participate in the formation of new bonds.
Q2) Which of the following statements about sigmatropic rearrangements and orbital symmetry is not true?
A) Reactions involving six atoms or fewer must take place by suprafacial pathways.
B) In a suprafacial rearrangement, the new \(\sigma\) bond forms on the opposite side of the \(\pi\) system as the broken \(\sigma\) bond.
C) In an antarafacial rearrangement, the new \(\sigma\) bond forms on the opposite side of the \(\pi\) system as the broken \(\sigma\) bond.
D) In a suprafacial rearrangement, the new \(\sigma\) bond forms on the same side of the \(\pi\) system as the broken \(\sigma\) bond.
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Chapter 28: Carbohydrates
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Q1) Does a monosaccharide prefer to exist in the open-chain or closed-ring form?
A) open
B) closed
C) Both forms exist in equal ratios.
Q2) From the disaccharides listed below, which one will not undergo mutarotation?
A) sucrose
B) maltose
C) lactose
D) xylobiose
Q3) 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
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Chapter 29: Amino Acids and Proteins
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Q1) Which one of the following naturally occurring amino acids does not have an S configuration?
A) cysteine
B) alanine
C) tyrosine
D) isoleucine
Q2) Why is the s-trans form of an amide bond more stable?
A) There is no s-cis form in an amide bond.
B) The oxygen is hydrogen-bonded with the nitrogen atom.
C) The nitrogen is able to be sp<sup>2</sup>-hybridized.
D) The more sterically bulky groups are farther apart.
Q3) Which of the following correctly describes a protein?
A) a dipeptide; two amino acids joined together by one amide bond
B) a tripeptide; three amino acids joined together by two amide bonds
C) a polymer of more than 40 amino acids joined together by amide bonds
D) a polypeptide of any number of amino acids joined together by amide bonds
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Chapter 30: Lipids
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Q1) What is the first key enzyme required for the synthesis of prostaglandins from arachidonic acid?
A) protein Kinase C
B) synthase
C) transferase
D) COX (cyclic oxygenase)
Q2) Which of the following fatty acids has the lowest melting point?
A) linoleic acid
B) oleic acid
C) arachidonic acid
D) palmitoleic acid
Q3) From the statements below, pick out the one that is not correct for fat-soluble vitamins.
A) Fat-soluble vitamins are classified as lipids.
B) Fat-soluble vitamins are a group of biologically active compounds containing 20 carbon atoms.
C) Fat-soluble vitamins are required in small quantities for normal metabolism.
D) Fat-soluble vitamins are stored in fat cells for use when they are needed.
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Chapter 31: Synthetic Polymers
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Q1) Which of the following is (are) addition polymer(s)? I. polypropylene
II) Teflon
III) nylon
A) Only I
B) Only II
C) Only III
D) Both I and II
Q2) Which of the following initiators can be used for free radical chain-growth polymerization?
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>
Q3) What is the name given to polymers that soften when heated and harden when cooled?
A) cross-linked polymers
B) copolymers
C) thermosetting polymers
D) thermoplastics
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