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Chemical Biology Final Test Solutions - 1479 Verified Questions

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Chemical Biology

Final Test Solutions

Course Introduction

Chemical Biology explores the interface of chemistry and biology, focusing on the use of chemical tools and principles to study and manipulate biological systems. This course covers a broad range of topics including the design and synthesis of molecules that probe or alter biological processes, chemical genetics, molecular recognition, and the chemical basis of enzyme function and signal transduction. Students will gain an understanding of how small molecules can be used to investigate cellular pathways, develop new therapeutic strategies, and advance research in areas such as drug discovery, biotechnology, and molecular medicine. The course integrates foundational concepts in organic chemistry, biochemistry, and cell biology to provide a comprehensive understanding of how chemical approaches drive innovation in biological research.

Recommended Textbook

Organic Chemistry 4th Edition by Janice Gorzynski

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Page 2

Chapter 1: Structure and Bonding

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Sample Questions

Q1) Which of the following covalent bonds has the largest dipole moment?

A) C-H

B) C-C

C) C-O

D) H-F

Answer: D

Q2) Which of the following statements about bonding is true?

A) Covalent bonds result from the transfer of electrons from one element to another.

B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.

C) Ionic bonds result from the sharing of electrons between two non-metals.

D) Covalent bonds result from the sharing of electrons between two metals.

Answer: B

Q3) Which of the following would you expect to have ionic bonds?

A) CO

B) FBr

C) NF<sub>3</sub>

D) NaCl

Answer: D

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3

Chapter 2: Acids and Bases

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Sample Questions

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 species is not a Brønsted-Lowry base?

A) BF<sub>3</sub>

B) NH<sub>3</sub>

C) H<sub>2</sub>O

D) PO<sub>4</sub><sup>3-</sup>

Answer: A

Q3) Which of the following statements about Lewis acids is true?

A) Lewis acids are proton donors.

B) Lewis acids are proton acceptors.

C) Lewis acids are electron pair donors.

D) Lewis acids are electron pair acceptors.

Answer: D

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4

Chapter 3: Introduction to Organic Molecules and Functional Groups

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Sample Questions

Q1) 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

Q2) What intermolecular force is generally considered the weakest?

A) Hydrogen bonding

B) London dispersion forces

C) Dipole-dipole

D) Ion-ion

Answer: B

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

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Chapter 4: Alkanes

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Sample Questions

Q1) What are the products of the combustion of alkanes?

A) Carbon and hydrogen

B) Carbon and water

C) Carbon dioxide and hydrogen

D) Carbon dioxide and water

Q2) What is the approximate C-C-C bond angle in propane?

A) 90°

B) 109.5°

C) 120°

D) 180°

Q3) Which of the following compounds has only primary and secondary hydrogen atoms?

A) 2-Methylpentane

B) 2,2,3-Trimethylpentane

C) 3-Methylpentane

D) 2,2-Dimethylpentane

Q4) Which of the following compounds has only primary and secondary carbon atoms?

A) Pentane

B) 2-Methylpentane

C) 2,2-Dimethylpentane

D) 2,3,3-Trimethylpentane

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Chapter 5: Stereochemistry

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Sample Questions

Q1) What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other?

A) 70

B) 85

C) 40

D) 30

Q2) Which of the following statements about stereoisomers is not true?

A) Stereoisomers have identical IUPAC names except for a prefix like cis or trans.

B) Stereoisomers differ in configuration.

C) Stereoisomers always have the same functional groups.

D) Stereoisomers differ only in their structural formula.

Q3) How many chiral stereoisomers can be drawn for dimethycyclopropane?

A) 1

B) 2

C) 3

D) 4

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Page 7

Chapter 6: Understanding Organic Reactions

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Sample Questions

Q1) Which of the following statements is true?

A) Bond dissociation energies increase down a column of the periodic table.

B) When \(\Delta\)H° is positive, more energy is released in forming bonds than is needed to break bonds.

C) When \(\Delta\)H° is negative, more energy is needed to break bonds than is released in forming bonds.

D) Bond dissociation energies decrease down a column of the periodic table.

Q2) 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.

Q3) 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.

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Chapter 7: Alkyl Halides and Nucleophilic Substitution

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Sample Questions

Q1) Rank the following molecules in order of increasing polarity, putting the least polar first. \[\begin{array} { c c c c }

\mathrm { CH } _ { 4 } & \mathrm { CH } _ { 3 } \mathrm { Cl } & \mathrm { CH } _ { 3 } \mathrm { Br } & \mathrm { CH } _ { 3 } \mathrm { I } \\

\text { I } & \text { II } & \text { III } & \text { IV } \end{array}\]

A) IV < III < II < I

B) I < IV < III < II

C) I < II < III < IV

D) II < I < III < IV

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.

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Chapter 8: Alkyl Halides and Elimination Reactions

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Sample Questions

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) Which of the following statements about the mechanism of an E2 reaction is not true?

A) It is fastest with tertiary halides.

B) It exhibits first-order kinetics.

C) A better leaving group should make a faster reaction.

D) All bonds are broken and formed in a single step.

Q3) Which of the following statements about an E1 mechanism is true?

A) The identity of the leaving group affects the rate of reaction.

B) The reaction follows second-order kinetics.

C) The reaction is slowest with tertiary substrates.

D) Polar aprotic solvents favor the E1 mechanism.

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Chapter 9: Alcohols, Ethers and Epoxides

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Sample Questions

Q1) Which of the following statements about the reaction of ethers with strong acids is true?

A) HCl, HBr and HI can all be used.

B) The mechanism of ether cleavage is S<sub>N</sub>1 only.

C) The mechanism of ether cleavage is S<sub>N</sub>2 only.

D) The mechanism of ether cleavage is S<sub>N</sub>1 and S<sub>N</sub>2.

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) Which of the following reactions will provide the best yield of ether by the Williamson ether synthesis?

A) Sodium methoxide and tert-butyl bromide.

B) Sodium tert-butoxide and iodomethane.

C) Methanol and tert-butyl alcohol in the presence of KOH.

D) Iodomethane and tert-butyl bromide in the presence of KOH.

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Page 11

Chapter 10: Alkenes

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Sample Questions

Q1) Which of the following statements about alkenes is not true?

A) They are less reactive than alkanes.

B) They can exist as cis/trans isomers.

C) The bond angle around the C-C double bond is approximately 120°.

D) The carbon of the C-C double bond is sp<sup>2</sup> hybridized.

Q2) 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

Q3) 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.

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Page 12

Chapter 11: Alkynes

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Sample Questions

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) How many degrees of unsaturation are introduced by a triple bond?

A) 0

B) 1

C) 2

D) 3

Q3) Which of the following statements about the reactions of alkynes is not true?

A) Alkynes contain easily broken \(\pi\) bonds.

B) Alkynes undergo addition reactions.

C) When alkynes undergo two sequential addition reactions, four new \(\sigma\) bonds are formed.

D) When alkynes undergo two sequential addition reactions, two new \(\sigma\)bonds and a \(\pi\) bond are formed.

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13

Chapter 12: Oxidation and Reduction

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Sample Questions

Q1) 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.

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) A compound X of molecular formula C<sub>8</sub>H<sub>12</sub> with no triple bonds reacts with one equivalent of H<sub>2</sub> to give a new compound having molecular formula C<sub>8</sub>H<sub>14</sub>. What can be inferred about the structure of compound X?

A) Compound X has 3 rings.

B) Compound X has 3 \(\pi\) bonds.

C) Compound X has 1 ring and 2 \(\pi\) bonds.

D) Compound X has 2 rings and 1 \(\pi\) bond.

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Chapter 13: Mass Spectrometry and Infrared Spectroscopy

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Sample Questions

Q1) Stronger bonds will be found where in the infrared spectrum?

A) Higher molecular weight

B) Lower molecular weight

C) Lower wavenumbers

D) Higher wavenumbers

Q2) 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

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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Sample Questions

Q1) Which of the following statements is true about electromagnetic radiation?

A) All molecules absorb electromagnetic radiation at some frequency.

B) Frequency is directly proportional to wavelength.

C) NMR uses the microwave region of the electromagnetic spectrum.

D) The radio frequency region of the electromagnetic spectrum has the largest energy per photon.

E) Energy is inversely proportional to 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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16

Chapter 15: Radical Reactions

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Sample Questions

Q1) What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide (NBS) to give 3-bromo-1-propene?

A) Cyclic bromonium ion

B) Allylic carbocation

C) Allylic carbanion

D) Allylic radical

Q2) Which of the following statements about chlorination is true?

A) The rate-determining step in chlorination is endothermic.

B) The transition state resembles the product.

C) The more stable radical is formed faster.

D) A mixture of products results.

Q3) Which of the following statements about chlorination and bromination is true?

A) Bromination is unselective, yielding a mixture of products.

B) Chlorination is often selective, yielding one major product.

C) Chlorination is faster than bromination.

D) Bromination is faster than chlorination.

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Chapter 16: Conjugation, Resonance, and Dienes

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Q1) Which of the following electronic transitions is common in the UV spectrum of 1,3-butadiene?

A) "\(\sigma\) \(\to\) \(\pi\)"

B) "\(\sigma\) \(\to\) \(\pi\)*"

C) "n \(\to\) \(\pi\)*"

D) "\(\pi\) \(\to\) \(\pi\)*"

Q2) 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

Q3) 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

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18

Chapter 17: Benzene and Aromatic Compounds

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Sample Questions

Q1) Where do the protons in benzene appear in the <sup>1</sup>H NMR spectrum?

A) Around 1600 cm<sup>-1</sup>

B) Around 120 ppm

C) Around 0 ppm

D) Around 7 ppm

Q2) 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.

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) Why is sulfuric acid used in aromatic nitration?

A) To keep the reaction from getting too basic

B) To form the active electrophile NO<sub>2</sub><sup>+</sup>

C) To protonate the aromatic ring

D) To keep the reaction from getting too acidic

Q2) 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.

Q3) Why is the nitro group a meta director?

A) Because it is sterically very large.

B) Because it adds electron density to the meta position, thus activating it.

C) Because it stabilizes the intermediate cation.

D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less.

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Chapter 19: Carboxylic Acids and the Acidity of the O-H

Bond

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Sample Questions

Q1) What is the overall charge of the amino acid, alanine, at pH = 10?

A) + 1

B) - 1

C) No overall charge

D) - 2

Q2) What would happen if a mixture of benzoic acid (C<sub>6</sub>H<sub>5</sub>COOH) and NaCl is added to a separatory funnel containing H<sub>2</sub>O and CH<sub>2</sub>Cl<sub>2</sub>?

A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer.

B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer.

C) Both benzoic acid and NaCl would dissolve in the organic layer.

D) Both benzoic acid and NaCl would dissolve in the water layer.

Q3) What is the hybridization of the carbon atom in a carboxy group?

A) sp

B) sp<sup>2</sup>

C) sp<sup>3</sup>

D) p

Page 21

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Chapter 20: Introduction to Carbonyl Chemistry;

Organometallic Reagents; Oxidation and Reduction

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Q1) What carbonyl compound and Grignard reagent could be used to prepare 2-butanol? \[\mathrm { CH } _ { 3 } \mathrm { CHO } / \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { MgBr } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHO } / \mathrm { CH } _ { 3 } \mathrm { MgBr } \quad \mathrm { CH } _ { 3 } \mathrm { COCH } _ { 3 } / \mathrm { CH } _ { 3 } \mathrm { MgBr }\]

\[\begin{array} { c c c }

\text { I } &&&&&&&& \text { II } &&&&&&&&\text { III }

\end{array}\]

A) Only I

B) Only II

C) Only III

D) Only I and II

Q2) What reagent can be used to cleave a silyl ether protecting group?

A) NaOMe

B) MeMgBr

C) Bu<sub>4</sub>NF

D) Pd/C

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Chapter 21: Aldehydes and Ketones Nucleophilic Addition

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Q1) 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.

Q2) 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

Q3) Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C. What accounts for this difference in boiling points?

A) Butanol is polar while butanal is not polar.

B) Butanol can exhibit dipole-dipole interactions while butanal cannot.

C) Butanol can hydrogen bond and butanal cannot hydrogen bond.

D) Butanal is less sterically hindered than butanol.

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Page 23

Chapter 22: Carboxylic Acids and Derivatives

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Q1) What is the first step in the general mechanism for nucleophilic acyl substitution?

A) Protonation of the carbonyl

B) Removal of an \(\alpha\)-proton

C) Addition of the nucleophile to the carbonyl

D) Loss of the leaving group

Q2) What is the direct product of the base-promoted hydrolysis of an ester?

A) A nitrile

B) A carboxylic acid

C) An amide

D) A carboxylic acid salt

Q3) Which of the following peaks would you see in the IR spectrum of a carboxylic acid?

A) A flat line (carboxylic acids are not IR active)

B) A sharp line at 2250 cm<sup>-1</sup>

C) A broad peak from 3800-2800 cm<sup>-1</sup>

D) A broad peak from 800-600 cm<sup>-1</sup>

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24

Chapter 23: Substitution Reactions of Carbonyl

Compounds at the Alpha-Carbon

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Q1) Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

A) Sodium hydroxide

B) Sodium methoxide

C) Sodium tert-butoxide

D) Sodium hydride

Q2) What are the three steps in the malonic ester synthesis?

A) Deprotonation, alkylation, hydrolysis/decarboxylation

B) Hydrogenation, alkylation, deprotonation

C) Alkylation, hydrolysis/decarboxylation. hydrogenation

D) Hydrolysis/decarboxylation, deprotonation, alkylation

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

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Chapter 24: Carbonyl Condensation Reactions

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Q1) What are the names for the two parts of the mechanism in a Robinson annulation?

A) Michael addition and intramolecular Claisen reaction

B) Michael addition and intramolecular aldol reaction

C) Claisen reaction and intramolecular aldol reaction

D) Aldol reaction and intramolecular Claisen reaction

Q2) The \(\beta\)-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product, what is the explanation for this result?

A) It undergoes elimination, since water is a good leaving group.

B) The hydroxy group is oxidized to a carbonyl.

C) The hydroxy group reacts with the carbonyl to form a ketal.

D) Hydroxide is eliminated via an enolate intermediate.

Q3) What is the general name for the class of products formed in an Aldol condensation reaction?

A) "\(\beta\),\(\gamma\)-unsaturated carbonyl compound"

B) "\(\alpha\),\(\beta\)-unsaturated carbonyl compound"

C) "\(\alpha\),\(\gamma\)-unsaturated carbonyl compound"

D) "\(\beta\)-hydroxy carbonyl compound"

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26

Chapter 25: Amines

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Q1) Rank the following compounds in order of increasing basicity, putting the least basic first. \[\begin{array} { c c c c } \mathrm { CH } _ { 3 } \mathrm { CONH } _ { 2 } & \mathrm { NH } _ { 3 } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 } & \left( \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \right) _ { 2 } \mathrm { NH } \\ \text { I } & \text { II } & \text { III } & \text { IV } \end{array}\]

A) II < III < IV < I

B) I < II < III < IV

C) IV < III < II < I

D) II < I < III < IV

Q2) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion. What does this tell you about the amine?

A) The amine is a primary amine.

B) The amine is a secondary amine.

C) The amine contains an even number of N atoms.

D) The amine contains an odd number of N atoms.

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Chapter 26: Carbon-Carbon Bond Forming Reactions in Organic Synthesis

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Sample Questions

Q1) What products are formed when diazomethane is heated?

A) methane gas and nitrogen gas

B) propene gas and nitrogen gas

C) methyl radical and nitrogen gas

D) methylene and nitrogen gas

Q2) Which of the following is true about the use of the Grubbs catalyst?

A) The Grubbs catalyst is used in carbon-carbon coupling reactions.

B) The Grubbs catalyst is used in alkene metathesis.

C) The Grubbs catalyst is used in carbene formation.

D) The Grubbs catalyst is used with palladium as a co-catalyst.

Q3) 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>.

Q4) Which of the following is not a step in the Suzuki reaction?

A) Oxidative addition of R-X to the palladium catalyst

B) Substitution of the R group to the palladium catalyst

C) Transfer of the alkyl group from the organoborane to palladium

D) Reductive elimination of R-R, forming the new C-C bond

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Chapter 27: Pericyclic Reactions

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Q1) Which of the following statements about pericyclic reactions is true?

A) Pericyclic reactions occur by way of ionic intermediates.

B) Pericyclic reactions occur by way of radical intermediates.

C) Pericyclic reactions involve multiple steps.

D) Reactive intermediates are not formed in pericyclic reactions.

Q2) Which of the following statements about a \(\pi\)-bonding molecular orbital is true?

A) A \(\pi\)-bonding molecular orbital is formed when two p orbitals of similar phase overlap.

B) A \(\pi\)-bonding molecular orbital is lower in energy than a \(\sigma\)-bonding molecular orbital.

C) A \(\pi\)-bonding molecular orbital is formed when two p orbitals of opposite phase overlap.

D) Both the statements "a \(\pi\)-bonding molecular orbital is formed when two p orbitals of similar phase overlap" and a \(\pi\)-bonding molecular orbital is lower in energy than a \(\sigma\)-bonding molecular orbital" are true.

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Chapter 28: Carbohydrates

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Q1) 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

Q2) Which of the following reagents would convert glucose into ethyl glucopyranoside?

A) EtBr, aq. HCl

B) EtOH, aq. HCl

C) EtOH, NaOH

D) Ag<sub>2</sub>O in NH<sub>4</sub>OH

Q3) Upon hydrolysis of cellulose, what sugar is formed?

A) sucrose

B) maltose

C) lactose

D) glucose

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Chapter 29: Amino Acids and Proteins

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Sample Questions

Q1) Why do amide bonds exist as reasonably stable s-cis or s-trans isomers at room temperature?

A) These amide bonds are not stable.

B) There is partial double bond character between the carbonyl carbon and the nitrogen atom.

C) The oxygen atom is hydrogen-bonded with the nitrogen atom.

D) The side-chains can form hydrogen bonds.

Q2) What is the separation of a racemic mixture into its component enantiomers called?

A) diastereomers

B) meso

C) resolution

D) neutralization

Q3) Which of the following is (are) globular protein(s)?

A) hemoglobin

B) keratins

C) collagens

D) elastins

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Chapter 30: Lipids

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Q1) What is the correct classification of the following compound?

CH<sub>3</sub>(CH<sub>2</sub>)<sub>15</sub>COOH

A) saturated triglyceride

B) simple lipid

C) wax

D) saturated fatty acid

Q2) Solid fats are generally from what source?

A) vegetables

B) starches

C) legumes

D) animals

Q3) How can an unsaturated fatty acid be converted into a saturated fatty acid?

A) hydrogenation

B) hydration

C) ozonolysis

D) hydrolysis

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Chapter 31: Synthetic Polymers

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Q1) Which type of polymerization process uses benzoyl peroxide (or other peroxides) as an initiator?

A) free-radical chain-growth

B) cationic chain-growth

C) anionic chain-growth

D) acid-catalyzed step-growth

Q2) Which one of the following monomers undergoes cationic polymerization most readily?

A) H<sub>2</sub>C=CH<sub>2</sub>

B) H<sub>2</sub>C=CHCH<sub>3</sub>

C) H<sub>2</sub>C=C(CH<sub>3</sub>)<sub>2</sub>

D) H<sub>2</sub>C=CHCN

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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