General Chemistry II Final Exam Questions - 3751 Verified Questions by Quizplus

General Chemistry II

Final Exam Questions

Course Introduction

General Chemistry II builds on foundational concepts introduced in General Chemistry I, delving deeper into the principles of chemical reactions, kinetics, equilibrium, thermodynamics, and electrochemistry. The course explores the behavior of acids and bases, solubility equilibria, and introduces students to coordination chemistry and nuclear processes. Emphasis is placed on quantitative problem-solving and laboratory skills, enabling students to analyze real-world chemical systems and comprehend the molecular basis of various chemical phenomena. This course is essential for students pursuing studies in chemistry, biology, engineering, and related scientific fields.

Recommended Textbook Organic Chemistry 3rd Edition by David R. Klein

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Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

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Q1) BF3 has a no dipole moment. Draw the Lewis structure for BF3, showing all nonbonding electrons. Indicate the polarity of every atom in the structure using + and - notation. Explain why the molecule has no net dipole.

Answer: 11ea894b_ac4f_ba1e_bba7_4bf101d49eeb_TB4454_00_TB4454_00 The trigonal planar geometry of BF3 results in the cancellation of individual bond dipoles, producing a net molecular dipole of zero.

Q2) Draw the Lewis structure for HCOOH and predict the hybridization state, molecular geometry and approximate bond angle around the central atom.

Answer: 11ea894b_ac4e_0c62_bba7_b5487186c235_TB4454_00_TB4454_00 sp2, trigonal planar, 1200

Q3) What force is NOT taken into account in the formation of a covalent bond?

A) repulsion between two positively charged nuclei

B) force of attraction between positively charged nuclei and negatively charged electrons

C) repulsion between two negatively charged nuclei

D) repulsion between positively charged nuclei and negatively charged electrons

Answer: D

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Chapter 2: Molecular Representations

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Q1) Draw a bond-line structure for each constitutional isomer with a molecular formula of C3H8O.

Answer: 11ea894b_ac5a_41b8_bba7_8136f3a24a5a_TB4454_00_TB4454_00

Q2) Draw significant resonance structures for the following compound, CH3CNO. Which of these is/are the most significant resonance structure(s)? Explain why.

Answer: 11ea894b_ac67_aec9_bba7_31df3277d7ef_TB4454_00_TB4454_00 Resonance structure II is most significant, because the more electronegative oxygen atom carries a negative formal charge.

Q3) Resonance structures have _______ connectivity of atoms and _______ distribution of electrons.

A) different, same

B) same, same

C) different, different

D) same, different

E) None of these

Answer: D

Q4) Draw the resonance hybrid of C6H6.

Answer: 11ea894b_ac68_7222_bba7_55525f20a2a7_TB4454_00_TB4454_00

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Chapter 3: Acids and Bases

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Q1) Which of the following is not a Brønsted -Lowry base?

A) CH3OH

B) CH3OCH3

C) CH3NH2

D) CH3CH3

E) None of these

Answer: D

Q2) What is the counterion in NaOCH2CH3?

A) Na+

B) NaO-

C) CH3CH2-

D) CH3CH2O-

Answer: A

Q3) Draw the conjugate acid of CH3OCH3

Answer: 11ea894b_ac6a_bc2d_bba7_b95ff4ea07c8_TB4454_00_TB4454_00

Q4) What is a counterion in (CH3)3COK?

Answer: K+

Q5) What is the leveling effect?

Answer: It is the deprotonation of a solvent by a base or protonation of solvent by an acid.

Page 5

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Chapter 4: Alkanes and Cycloalkanes

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Q1) Identify the size of the hydrocarbon that is used in asphalt.

A) C1 - C4

B) C5 - C12

C) C12 - C18

D) C12 and higher

Q2) What is the structure of 1-cyclopropyl-3-methylcyclopentane?

Q3) Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.

Q4) Draw a chair conformation of ethylcyclohexane with the ethyl group axial.

Q5) Draw the lowest energy chair conformer of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.

Q6) Draw the most stable conformation of trans-1,4-diethylcyclohexane.

Q7) Draw an energy diagram for the conformational analysis of propane.

Q8) Draw a chair conformation of cyclohexane showing all of the equatorial H's.

Q9) What is the structure of an isopropyl group?

Q10) Give the structures and IUPAC names of all constitutional isomers of C6H14.

Page 6

Q11) What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol?

Q12) What is the structure of 3-ethyl-2,4,6-trimethyloctane?

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Chapter 5: Stereoisomerism

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Q1) What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is 61?

A) 25.5%

B) 51%

C) 49%

D) 74.5%

Q2) What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of 52?

A) 61

B) 64

C) 0

D) 61

Q3) What is the % ee of a sample of carvone that exhibits a specific rotation of 20, given that the specific rotation of (R)-carvone is 61?

Q4) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -CH3 II. -CN III. -CH2OH IV. -Br

Q5) Draw the structure of the compound (S)-3-methylheptane.

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Chapter 6: Chemical Reactivity and Mechanisms

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Sample Questions

Q1) Draw an energy diagram for an endothermic reaction with two steps.

Q2) Why is the entropy change negative for ring closures?

A) Closing a ring results in fewer molecules.

B) Closing a ring results in more molecules.

C) Closing a ring releases energy.

D) Closing a ring restricts the rotation around individual carbon-carbon bonds.

Q3) Identify the nucleophilic atom in the following molecule, Me3P.

A) P

B) C

C) H

D) Me

Q4) What is a transition state?

A) An isolable intermediate in a reaction.

B) The starting materials of the reaction.

C) A local maximum on the energy diagram.

D) A low-energy point between the starting materials and the product.

Q5) Draw an energy diagram for a concerted exothermic reaction.

Q6) Does a reaction with a H of 14 kJ/mol and a S of 150 J/mol·K at 298 K favor reactants or products?

Q7) Does a reaction with a value of 0 for G favor reactants or products?

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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

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Q1) When drawing a curved arrow mechanism, the tail of the arrow starts at______.

A) the bond that is being formed

B) the atom with the positive charge

C) the source of electrons that is being moved

D) the location to which the electrons are being moved

Q2) Which of the following is a weakest nucleophile in a polar protic solvent?

A) F-

B) Cl-

C) Br-

D) I-

E) All of these

Q3) Which of the following is NOT a nucleophile?

A) OH-

B) NH3

C) CH3OH

D) NH4+

E) All of these

Q4) Draw the Z isomer of 3,4-dimethyl-3-hexene.

Page 10

Q5) Draw the E isomer of 2-methyl-3-heptene.

Q6) Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.

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Chapter 8: Addition Reactions of Alkenes

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Q1) Give the expected product(s) resulting from addition of Br2 to (E)-3-hexene.

A) a meso dibromide

B) a mixture of optically active enantiomeric dibromides

C) a mixture of diasteromeric isomers

D) (Z)-3,4-dibromo-3-hexene

E) (E)-3,4-dibromo-3-hexene

Q2) Give the best description of the regioselectivity and stereospecificity in the oxymercuration of an alkene.

A) Markovnikov orientation with syn-addition

B) Markovnikov orientation with anti-addition

C) anti-Markovnikov orientation with syn-addition

D) anti-Markovnikov orientation with anti-addition

E) Markovnikov orientation with both syn- and anti-addition

Q3) The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?

Q4) The alkene precursor to acetone is __________.

Q5) Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

Page 12

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Chapter 9: Alkynes

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Q1) What is the IUPAC name for di-sec-butylacetylene?

A) 2-ethyl-5-methyl-3-heptyne

B) 2,7-dimethyl-4-octyne

C) 3,6-dimethyl-4-octyne

D) 2,5-diethyl-3-hexyne

E) 2,2,5,5-tetramethyl-3-hexyne

Q2) How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne, in the presence of a palladium catalyst?

A) 1

B) 2

C) 3

D) 6

E) 8

Q3) Which of the bases below would quantitatively deprotonate a terminal alkyne?

A) BuLi

B) NH3

C) NaOH

D) NaOCH2CH3

E) t-BuOK

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Chapter 10: Radical Reactions

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Q1) Free radical chlorination of ethane can produce higher halogenation products such as dichloroethane, trichloroethane, tetrachloroethane, pentachloroethane, and hexachloroethane. How could the production of higher halogenated products be minimized?

A) use an excess of chlorine

B) use an excess of ethane

C) use equimolar chlorine and ethane

D) it is not possible to minimize the production of higher halogenated products

Q2) Which of the following compounds would be expected to be least destructive to the ozone layer?

A) CCl3F

B) CCl2F2

C) CCl2FCCl2F

D) CF3CH2F

Q3) Propose a synthesis of polyethylene from ethane.

Q4) Compound A has molecular formula C6H12. Upon treatment with NBS and irradiation with UV light, exactly two compounds (including stereoisomers), are formed. Suggest a possible structure for compoundA.

Q5) Propose a synthesis of 4-penten-2-ol from propene.

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Chapter 11: Synthesis

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Q1) Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond

B) substitute bromide with acetylide, then reduce the alkyne to an alkene

C) substitute bromide with methoxide

D) eliminate hydrogen bromide to produce an alkene, then cleave the double bond

Q2) Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

Q3) Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond

B) substitute bromide with acetylide, then reduce the alkyne to an alkene

C) substitute bromide with methoxide

D) eliminate hydrogen bromide to produce an alkene

Q4) Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

Q5) 2-Methylpentane (C6H14) can be converted, through a multistep synthesis, to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

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Chapter 12: Alcohols and Phenols

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Sample Questions

Q1) Identify the characteristics of the hydroboration-oxidation of an alkene.

A) Markovnikov, with rearrangement possible

B) Markovnikov, with no rearrangement possible

C) anti-Markovnikov, with rearrangement possible

D) anti-Markovnikov, with no rearrangement possible

Q2) Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.

Q3) Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural drawings to explain your reasoning.

Q4) Identify grain alcohol.

A) methanol

B) 2-propanol

C) ethanol

D) 1-butanol

E) 1-propanol

Q5) What is the IUPAC name for isobutyl alcohol?

A) 2-methyl-1-propanol

B) 2-methyl-1-butanol

C) 1-methyl-1-propanol

D) 1,1-dimethyl-1-ethanol

E) 3-methyl-1-propanol

Page 16

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Chapter 13: Ethers and Epoxides; Thiols and Sulfides

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Q1) Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane.

Q2) Which of the following crown ether solvates sodium ions?

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Q3) Draw all constitutional isomers with molecular formula C6H14O having an ether functional group and provide the IUPAC name for each isomer.

Q4) Which one of the following compounds will be least soluble in water?

A) diethyl ether

B) methyl propyl ether

C) 1-butanol

D) 2-butanol

E) pentane

Q5) What is the correct structure for 3-methyl-1-hexanethiol?

Q6) Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane.

Q7) Explain why long-term storage of ethers can be dangerous.

Q8) Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene.

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Chapter 14: Infrared Spectroscopy and Mass Spectrometry

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Q1) Which of the following is expected to be the base peak in the mass spectrum of CH3CH2NH2?

A) 15

B) 28

C) 30

D) 45

E) none of these

Q2) Propose a possible structure for a compound with molecular formula C7H12O2 that shows absorption at 1720 cm-1 and no absorption in the range of 1500 - 1700 cm-1 or 2600 - 2800 cm-1 in its IR spectrum.

Q3) A compound with molecular formula C4H8O2, shows absorptions at 2500-3300 cm-1 (broad), 1720 cm-1 and at 1200 cm-1 on the IR spectrum. Propose a possible structure for this compound.

Q4) Warmer objects emit more __________ radiation.

Q5) Provide the structure of the major fragment that results when the molecular ion of (CH3)2CHCH2CH2NH2 undergoes fragmentation.

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Chapter 15: Nuclear Magnetic Resonance Spectroscopy

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Q1) Which of the following type(s) of protons are chemically non-equivalent?

A) homotopic

B) enantiotopic

C) diastereotopic

D) A & B

E) B & C

Q2) _______ protons experience a net magnetic field strength that is smaller than the applied magnetic field.

A) Deshielded

B) Shielded

C) Paramagnetic

D) Diamagnetic

E) none of these

Q3) How many signals would you expect in the 1H NMR spectrum of HOCH2CH2CH2CH2OH?

A) 1

B) 2

C) 3

D) 4

E) 5

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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions

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Q1) Identify the cumulated diene.

A) 4-methyl-1,3-heptadiene

B) 3-methyl-1,5-heptadiene

C) 2-methyl-2,4-heptadiene

D) 4-methyl-1,4-heptadiene

E) 5-methyl-2,3-heptadiene

Q2) Which of the following is most useful to study conjugation in organic compounds?

A) IR spectroscopy

B) NMR spectroscopy

C) Mass spectroscopy

D) UV-Vis spectroscopy

E) Raman spectroscopy

Q3) Which of the following symbols is used to represent the molar absorptivity of a given compound in the UV-Vis region?

A) (\(\lambda\))

B) (\(\varepsilon\))

C) (\(v\))

D) (\(\gamma\))

E) (\(\alpha\))

Q4) Identify the light-sensitive compound in rods.

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Chapter 17: Aromatic Compounds

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Q1) What is the structure for p-aminobenzoic acid (PABA)?

Q2) Identify the functional group in acetophenone.

A) ether

B) alkene

C) carboxylic acid

D) aldehyde

E) ketone

Q3) When the benzene ring is treated as a substituent, it is called a _________ group

Q4) Provide the reagent(s) necessary to convert toluene to benzoic acid.

Na2Cr2O7/H2SO4/H2O

B) 1. NBS, \(\Delta\) 2.NaOH

C) 1. LiAlH4 2. H3O+

D) H2, Pd

E) 1. CO2, 2. H3O+

Q5) What is the structure for 1,3-diphenylbutane?

Q6) What is the structure for 3-isobutyl-5-isopropylaniline?

Q7) Provide the reagents necessary to convert ethylbenzene to styrene.

Q8) Molecular orbitals of equal energy are referred to as _________ orbitals.

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Chapter 18: Aromatic Substitution Reactions

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Q1) Identify the reagents used to carry out the chlorination of benzene.

A) Cl2/CCl4

B) Cl2/FeCl3

C) Cl2/AlCl3

D) NaCl/Fe

E) both B and C

Q2) List the three steps involved in an electrophilic aromatic substitution reaction.

Q3) Which of the following substituents will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH2CH3

B) -CF3

C) -OCH3

D) -COOCH3

E) both A and C

Q4) Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E+).

Q5) Draw the major resonance contributors for the intermediate that results when p-chloronitrobenzene is treated with NaOH.

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Chapter 19: Aldehydes and Ketones

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Q1) Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.

Q2) The 13C NMR spectrum of a compound with formula C7H14O shows five signals. Which one of the following is a possible structure for this compound?

A) 2-heptanone

B) 3-heptanone

C) 2,2-dimethyl-3-pentanone

D) 2,4-dimethyl-3-pentanone

E) none of these

Q3) Provide the structure for m-nitroacetophenone.

Q4) Provide a structure for the compound with molecular formula C5H10O and with the following spectroscopic data. IR: 1720 cm 1 1H NMR: 0.9 \(\delta\) (triplet, 3H), 1.7 \(\delta\) (sextet, 2H), 2.1 \(\delta\) (singlet, 3H), 2.4 \(\delta\) (triplet, 2H)

Q5) Suggest a stepwise synthesis for 3-phenylpropanal from benzyl alcohol.

Q6) Provide the structure for benzophenone.

Q7) Provide the structure for 2,3-dimethyl-2-octen-4-one.

Page 23

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Chapter 20: Carboxylic Acids and Their Derivatives

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Q1) A compound with molecular formula C9H10O2 exhibits a triplet at \(\delta\) 1.2 (3H), a quartet at \(\delta\) 2.6 (2H), a doublet at \(\delta\) 7.3 (2H), a doublet at \(\delta\) 8.0 (2H) and a singlet at \(\delta\) 11 (1H) in its 1H NMR spectrum. What is the structure for this compound?

Q2) Provide the structure for 5-chloro-3-isopropyloctanoic acid.

Q3) Provide the structure for acetic formic anhydride.

Q4) Provide the structure for 3-ethylbenzonitrile.

Q5) Give the IUPAC name for oxalic acid.

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Q6) Give the IUPAC name for glutaric acid.

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Page 24

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Chapter 21: Alpha Carbon Chemistry: Enols and Enolates

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

A) sodium hydroxide

B) sodium ethoxide

C) LDA

D) sodium hydride

E) both C and D

Q2) Identify a reactive starting material in the Claisen condensation.

A) 3-pentanone

B) butanal

C) ethyl butanoate

D) 1-propanol

E) propanoic anhydride

Q3) Explain why CH3ONa should not be used for Claisen condensation of ethylbutanoate.

Q4) Provide the structure of the enolate when acetophenone is treated with a strong base.

Q5) An intermolecular Claisen condensation is called a _____________.

Q6) Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.

Page 25

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Chapter 22: Amines

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Q1) Which one of the following is the best synthesis for 3,5-dibromotoluene?

A) toluene, Br2/FeBr3 excess

B) 1. p-toluidine, Br2/ FeBr3;

2) NaNO2/HCl, < 5°C

3) H3PO2

C) 1. Toluene, HNO3/H2SO4

2) NH3

3) NaNO2/HCl, < 5°C

4) CuBr

D) m-dibromobenzene, CH3Cl/AlCl3

E) 1. m-bromotoluene, HNO3, H2SO4

2) Fe/HCl

3) NaNO2/HCl, < 5°C

4) CuBr

Q2) Provide the reagents necessary to convert (S)-3-methyl-3-phenylpentanoic acid to (S)-3-methyl-3-phenylpentanamine.

Q3) Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C followed by o-ethylphenol?

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Chapter 23: Introduction to Organometallic Compounds

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Q1) Which of the following electrophiles are commonly used with Gilman reagents to form C-C bonds? Select all that apply.

A)acid chlorides

B) , -unsaturated ketones

C)esters

D)alkyl halides

E)amides

Q2) Starting from vinyl chloride and ________ as the only source of carbon atoms, 1-heptene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

A) 1-bromopropane

B) 2-bromopentane

C) 1-bromohexane

D) 1-bromopentane

Q3) Which of the following compounds has the most nucleophilic carbon atom?

A) CH3Cl

B) CH3Li

C) (CH3)2Zn

D) (CH3)2Cu

Q4) Explain why the solvent for a Grignard reaction must be free of water.

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Chapter 24: Carbohydrates

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Q1) Which one of the following heterocyclic amines is not a base in RNA?

A) uracil

B) thymine

C) cytosine

D) adenine

E) guanine

Q2) Identify the classification for D-ribose.

A) aldotetrose

B) ketotetrose

C) aldopentose

D) ketopentose

E) aldohexose

Q3) Identify the monomer in glycogen.

A) (\(\alpha\)-D-glucose)

B) (\(\beta\)-D-glucose)

C) (\(\alpha\)-D-galactose)

D) (\(\beta\)-D-fructose)

E) maltose

Q4) Identify the monosaccharide(s) in \(\alpha\)-maltose.

Q5) Draw the Fisher projection for D-galactose.

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Chapter 25: Amino Acids, Peptides, and Proteins

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133 Verified Questions

133 Flashcards

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Sample Questions

Q1) The ______ of amino acids in a protein is referred to as its primary structure.

A) twisting

B) sequence

C) folding

D) bonding

E) reacting

Q2) Cooking an egg is an example of ________________, and is irreversible.

Q3) Which of the following tetrapeptides is not cleaved by trypsin?

A) Gly-Lys-Cys-Phe

B) Cys-Ala-Arg-Ser

C) Gly-Ser-Ile-Lys

D) Ala-Lys-Tyr-Arg

E) Lys-Met-Pro-Ala

Q4) When thirty amino acids are connected to each other, they form ____________.

A) a tripeptide

B) a protein

C) a polypeptide

D) a tetrapeptide

E) none of these

Q5) Provide the structure of the predominant form of alanine at pH 2?

Page 29

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Chapter 26: Lipids

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Sample Questions

Q1) How many different structures (including stereoisomers) are possible for a triglyceride that contains one palmitic acid residue, one arachidic acid residue and one stearic acid residue?

A) 3

B) 6

C) 9

D) 12

E) 15

Q2) Which of the following fatty acid(s) is not likely to be present in natural fats and oils?

A) octadecanoic acid

B) heptadecanoic acid

C) hexadecanoic acid

D) octadeca-9,12-dienoic acid

E) none of these

Q3) A triglyceride produced a linoleic acid residue, a palmitoleic acid residue and an oleic acid residue, when heated in the presence of an acid. Provide one of the possible structures for this triglyceride.

Q4) ______lipids undergo hydrolysis in the presence of aqueous acid or base.

Q5) Male sex hormones are called ______ and female sex hormones are called ____.

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Chapter 27: Synthetic Polymers

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119 Verified Questions

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Sample Questions

Q1) Identify the polymer used in plumbing.

A) polytetrafluoroethylene

B) polystyrene

C) polypropylene

D) polyethylene

E) poly(vinyl chloride)

Q2) ________ regions in polymers make the polymer hard and durable.

A) amorphous

B) cross linked

C) crystalline

D) A and B

E) B and C

Q3) Which of the following monomer(s) would undergo both radical and cationic polymerization?

A) methyl methacrylate

B) acrylonitrile

C) isobutylene

D) vinylidene chloride

E) all of these

Q4) Give the monomers to form PET.

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