Organic Chemistry: Chapters 8-10

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Questions and Answers

Which spectroscopic technique is most useful for determining the presence of a carbonyl group in an unknown organic compound?

  • ¹³C NMR
  • ¹H NMR
  • Mass Spectrometry
  • Infrared (IR) Spectroscopy (correct)

What is the expected major product when 2-methyl-2-butene reacts with HBr?

  • 2-bromo-2-methylbutane (correct)
  • 3-bromo-2-methylbutane
  • 2-bromo-3-methylbutane
  • 1-bromo-2-methylbutane

Which reagent is best suited for converting an alkene to a syn-diol?

  • mCPBA
  • Hâ‚‚ with Pd/C
  • OsOâ‚„ (correct)
  • KMnOâ‚„, NaOH, cold

What type of intermediate is formed during the epoxidation of an alkene with a peroxyacid?

<p>Concerted (D)</p> Signup and view all the answers

Which of the following reagents is used in the Simmons-Smith reaction?

<p>$CH_2I_2$ and Zn(Cu) (C)</p> Signup and view all the answers

Which of the following best describes the product of ozonolysis of an alkene followed by treatment with a reducing agent such as dimethyl sulfide ($DMS$)?

<p>A ketone and an aldehyde (D)</p> Signup and view all the answers

What is the product of the reaction of 1-butyne with $H_2$ and Lindlar's catalyst?

<p>1-butene (D)</p> Signup and view all the answers

Which of the following reagents will convert an internal alkyne to a trans-alkene?

<p>$Na, NH_3(l)$ (B)</p> Signup and view all the answers

What type of reaction is the conversion of an alkyne to a ketone using $H_2O, H_2SO_4, HgSO_4$?

<p>Hydration (C)</p> Signup and view all the answers

Which of the following reagents can be used to deprotonate a terminal alkyne?

<p>NaNHâ‚‚ (C)</p> Signup and view all the answers

What is the product of the reaction of 1-hexyne with ozone ($O_3$) followed by dimethyl sulfide ($DMS$)?

<p>Pentanoic acid and formic acid (C)</p> Signup and view all the answers

Which of the following is the strongest nucleophile in a polar protic solvent?

<p>$I^-$ (D)</p> Signup and view all the answers

Which of the following is a polar aprotic solvent?

<p>Acetone ($(CH_3)_2CO$) (A)</p> Signup and view all the answers

Which of the following is the best leaving group?

<p>$I^-$ (A)</p> Signup and view all the answers

What is the rate-determining step in an $S_N2$ reaction?

<p>Simultaneous bond breaking and bond forming (C)</p> Signup and view all the answers

Which of the following substrates will react fastest in an $S_N2$ reaction?

<p>$CH_3-Br$ (D)</p> Signup and view all the answers

What is the stereochemical outcome of an $S_N2$ reaction at a chiral center?

<p>Inversion of configuration (C)</p> Signup and view all the answers

Which factor primarily influences the rate of an $S_N2$ reaction?

<p>Concentration of the substrate and nucleophile (B)</p> Signup and view all the answers

Consider a multistep synthesis. What is the first step in devising a synthesis for a target molecule?

<p>Working backward from the product to the starting material (C)</p> Signup and view all the answers

Which of the following is the most important consideration when proposing steps in a multistep synthesis?

<p>Maximizing the yield in each step (B)</p> Signup and view all the answers

Flashcards

Alkene Halogenation

Adding a halogen (like Clâ‚‚ or Brâ‚‚) to an alkene.

Halohydrin Formation

A reaction where a halogen and a hydroxyl group (-OH) are added to an alkene.

Hydroboration-Oxidation

A two-step process that converts an alkene into an alcohol via syn addition.

Oxymercuration-Demercuration

Converts alkenes to alcohols using mercury(II) acetate.

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Alkene Hydration

Adding water (Hâ‚‚O) to an alkene, typically requiring an acid catalyst.

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Alkene Hydrogenation

Adding hydrogen (Hâ‚‚) to an alkene, typically with a metal catalyst (e.g., Pt, Pd, Ni).

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Epoxide

A three-membered ring containing an oxygen atom.

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Alkene Ozonolysis

Cleavage of an alkene using ozone (O₃) to form carbonyl compounds (aldehydes or ketones).

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KMnOâ‚„ Oxidation

Oxidation of an alkene with potassium permanganate (KMnOâ‚„) to form diols (syn-dihydroxylation).

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Cyclopropanation

Reaction to form a three-membered carbon ring using a carbene.

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Simmons-Smith Reaction

A metal-catalyzed reaction where a carbene adds to an alkene, forming a cyclopropane ring.

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Alkyne Hydrohalogenation

A reaction where a hydrogen halide (e.g., HCl, HBr) is added to an alkyne.

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Alkyne Halogenation

Addition of a halogen (like Clâ‚‚ or Brâ‚‚) to an alkyne.

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Alkyne Hydration (Acid Catalyzed)

Adding water (Hâ‚‚O) to an alkyne, typically requiring a mercury(II) catalyst.

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Lindlar's Catalyst

Reduces an alkyne to a cis-alkene using hydrogen gas and a poisoned palladium catalyst.

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Dissolving Metal Reduction

A reaction that reduces an alkyne to a trans-alkene using sodium or lithium metal in liquid ammonia.

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Alkyne Ozonolysis

Cleavage of an alkyne using ozone (O₃) to form carboxylic acids.

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Substitution Reaction

Replacing a leaving group with a nucleophile.

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Polar protic solvent

Solvents with hydrogen bond donors.

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Polar aprotic solvent

Solvents without hydrogen bond donors

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Study Notes

  • The exam covers all of chapter 8, all of chapter 9, and selected topics from chapter 10.

Chapters 4-6

  • Interpret mass, infrared, ¹H NMR, and ¹³C NMR spectra to determine the molecular formula and structure of unknown compounds.

Chapter 8: Electrophilic Addition Reactions of Alkenes

  • Recognize, understand, describe, and predict products, reactants, and conditions.
  • Understand regiochemistry and stereochemistry.
  • Write mechanisms for electrophilic addition reactions of alkenes, including:
  • Halogenation
  • Halohydrin Formation
  • Hydroboration Oxidation
    • Mechanism for Step 2 is not required
  • Oxymercuration Oxidation
    • Mechanism for Step 2 is not required
  • Hydration
  • Hydrogenation
    • No mechanism required
  • Epoxidation
  • Ring-opening of an epoxide
  • Syn-dihydroxylation using OsOâ‚„
    • No mechanism required
  • Ozonolysis
    • No mechanism required
  • Potassium permanganate oxidation
    • No mechanism required
  • Periodic acid oxidation
    • No mechanism required
  • Carbene synthesis
    • No mechanism required
  • Cyclopropanation using a carbene
  • Simmons-Smith cyclopropanation
    • No mechanism required

Chapter 9: Terminal Alkynes

  • Describe the relative acidity of terminal alkynes.
  • Propose acid-base reactions where a terminal alkyne acts as an acid.
  • Recognize, understand, describe, and predict products, reactants, and conditions.
  • Reactions include regiochemistry and stereochemistry.
  • Write mechanisms for electrophilic addition reactions of alkenes, including:
  • Hydrohalogenation
  • Halogenation
  • Acid-catalyzed hydration and mercury-catalyzed hydration
    • No mechanism required
  • Keto-enol and aldo-enol tautomerization
    • Base mechanism not required; acid is required
  • Hydroboration-oxidation
    • No mechanism required
  • Catalytic hydrogenation
    • No mechanism required
  • Reduction using a poisoned catalyst (Lindlar’s catalyst)
    • No mechanism required
  • Dissolving metal reduction
    • No mechanism required
  • Ozonolysis
    • No mechanism required
  • Potassium permanganate oxidation
    • No mechanism required
  • Alkylation of a terminal alkyne
  • Synthesis of an alkyne from dihalide
    • No mechanism required

Chapter 10: Substitution Reactions

  • Define substitution reactions.
  • Distinguish between good and bad leaving groups.
  • Differentiate between polar protic and polar aprotic solvents.
  • Differentiate between strong bases, weak bases, strong nucleophiles, and weak nucleophiles.
  • Describe the details of an Sâ„–2 reaction including:
    • Rate equation
    • Mechanism
    • Energy diagram
    • Transition state
    • Substrate effects
    • Leaving group effects
    • Nucleophile effects
    • Solvent effects
    • Stereochemical outcome

Chapters 8-10: Multistep Synthesis

  • Propose the starting material for a multistep synthesis of a target molecule.
  • Propose the product of a multistep synthesis.
  • Propose the steps and/or intermediates of a multistep synthesis.

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