Quiz 2- Ch 17&18 (alcohols, ethers, epoxides, thiols, sulfides)

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Last updated 1:56 AM on 7/19/26
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45 Terms

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Williamson Ether Synthesis

R’ must be primary or methyl to favor substitution over elimination

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Alkoxymercuration-Demercuration

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Acidic Cleavage of an Ether

*in 2nd step, the alkyl carbon on the protonated alcohol undergoes Sn2 by X-

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Autooxidation of Ethers

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Epoxide formation from halohydrins

halohydrin is treated with a base, the -OH is deprotonated to give an alkoxide. The alkoxide undergoes a kind of intramolecular Sn2, where the O- attacks the carbon bonded to the halogen group, forming an epoxide

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Epoxide Ring Opening using a nucleophile under basic conditions

the nucleophile always adds to the less substituted carbon

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Epoxide Ring Opening using a nucleophile under acidic conditions

the nucleophile adds to the more substitution carbon if the substrate is a tertiary carbon, it adds to the less substituted carbon if the substrate is a primary or secondary carbon.

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Oxidation of Thiols

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Sulfide formation from Thiols

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Epoxide formation from an alkene

Reagent: RCO3H (like mCPBA)

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De-protonation of alcohols

Reagents: NaH, NaNH2, Na or K

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De-protonation of phenols to form anisole

reagent: 1. NaOh / 2. CH3I

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Preparation of Alcohols: Acid Catalyzed Hydration

reagents: H2SO4 or H3PO4

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Preparation of Alcohols: Oxymercuration-Demercutation

reagents: 1. Hg(OAc)2, H2O / 2. NaBH4

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Preparation of Alcohols: Hydroboration-Oxidation

reagents: 1. BH3, THF / 2. H2O2, NaOH

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Preparation of Diols: Syn Dihydroxylation

reagents: OsO4

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Preparation of Diols: Anti Dihydroxylation

reagents: RCO3H (mcPBA)

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Aldehydes, Carboxylic Acids, and Esters reduce to…

primary alcohols

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Ketones reduce to…

secondary alcohols

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reduction of a ketone using 1. NaBH4 / 2. H3O+

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reduction of a ketone using 1. LiAlH4 / 2. H3O+

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reduction of a Carboxylic Acid

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reduction of an ester to an alcohol

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Grignard reagent formation

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Grignard Reactions with a ketone

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Grignard reactions with an ester

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Grignard reactions with an epoxide

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Grignard reactions with CO2

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Reactions of alcohols: tertiary alcohols undergo…

SN1

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Reactions of alcohols: secondary and primary alcohols undergo…

SN2

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Alcohol + H-X

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Alcohol + SOCl2 / pyridine

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Alcohol + PBr3

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Protection of Alcohols using Tosylate

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Net Retention of a Chiral Center:

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Net Inversion of a Chiral Center:

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Acid Catalyzed Dehydration

reagents: H2SO4

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Oxidation of Alcohols: reagents

CrO3 / H2SO4, H2CrO4, Na2Cr2O7, or K2Cr2O7

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Secondary alcohols oxidize to form….

ketones

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Primary alcohols oxidize to form…

carboxylic acids

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Tertiary alcohols oxidize to form…

tertiary alcohols do not react

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Oxidation of a secondary alcohol

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Oxidation of a primary alcohol

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Oxidation of a primary alcohol to an aldehyde

PCC or Dess-Martin/ CH2CH3

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Quinone formation

phenol + Na2CrO7 / H2O