CHEM 3570 - Prelim 3, Alcohols, Thiols, Ethers, Epoxides, Glycols

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Last updated 7:04 PM on 4/22/26
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28 Terms

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thiol

R-SH

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more branched alcohol means..

less acidic (less stable conjugate base due to hindrance of solvation)

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Formation of Thiolate/Aloxides

  1. React with NaH/KH with aprotic solvent

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Dehydration/Protonation of Alcohols

  1. Makes a better leaving group

  2. H3PO4 or H2SO4

  3. becomes E1 rxn

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Alcohols with HX

  1. can happen with Sn1 and Sn2

  2. protonate alcohol to good leaving group

  3. sn1 faster

  4. For SN1: H-X, H2O

  5. For Sn2: H-x, Aprotic

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Preparation of OTs/OMs groups

  1. TsCl and Pyridine

  2. retention of stereochemistry

  3. they are good leaving groups/weak bases

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Alcohols - Chlorides (inversion)

  1. SOCl2 in pyridine

  2. like SN2

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Alcohols - Bromides (inversion)

  1. PBr in DMF

  2. like SN2

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Oxidation of Alcohols (overview of degrees)

  1. 3º - no oxidation bc no alpha hydrogens

  2. 2º - ketone product

  3. 1º - aldehyde or carboxylic acid

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Oxidation of 2º Alcohols

  1. CrO42- in acidic conditions, or CrO3 in pyradine

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Oxidation of 1º Alcohols

  1. K2Cr2O7 in H2SO4 and H2O - overoxidize to carboxylic acid

  2. CrO3(pyridine)HCl in Ch2Cl2 - Aldehyde

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Oxidation of Thiols - Disulfide

  1. (2RSH) in Br2 or I2

  2. weak oxidant

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Oxidation of Thiols - Sulfonic Acid

  1. RSH in HNO3/H2O

  2. stronger oxidation

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glycol

1,2 diol

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Synthesis of Ethers (2 ways)

Sn2 williamson ether, alkoxymercuration-reduction

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SN2 Williamson Ether/Sulfide Reaction

  1. Strong base (NaH), then primary alkane

  2. convert to alkoxide (or thiolate), then SN2 to get the ether/sulfide

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Alkoxymercuration-Reduction of Alkene to obtain an Ether

  1. Hg(OAc)2 in HO-R, then NaBH4 in NaOH

  2. anti addition of the OR and HgOAc, then becomes ether

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Reactivity of Ethers with H-I

  1. Ether is reactive in strong acid

  2. Is protonated by H+, SN2 rxn, then again the alcohol is protonated to good LG and SN2 again

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Synthesis of Epoxides (2 ways)

One step peroxyacid (mCPBA), Halohydrins (2 steps)

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Synthesis of Epoxide with peroxyacid

  1. using mcPBA in DCM

  2. one step concerted

  3. syn addition

  4. forms racemic

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Synthesis of Epoxide with Halohydrins

  1. Br2 in H20, then NaOH

  2. turns to halohydrin (anti b/c halonium ion), then SN2 with OH-

  3. must be diaxial/trans for SN2 sterics

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Reactivity of Epoxides (Openings) (2 ways)

Acid/Base, Grignard (both anti)

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Acid/Base opening of Epoxides

  1. Acid: Nucleophile in Conj. Acid

  2. nucleophile attacks less subbed

  3. Base: Acid in Nucleophile

  4. nucleophile attacks more subbed

  5. anti

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Epoxide Opening with Grignard Reagent

  1. recall carbanion characteristic

  2. R - MgBrin ether and H30+

  3. Sn2 attack by R- MgBr, O- protonated by H3O+

  4. SN2 will attack least subbed

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Synthesis of Glycols/Diols (2 ways)

  1. Acid/Base catalyzed epoxide opening (trans)

  2. Dihydroxylation of an Alkene (cis)

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Synthesis of Glycol with Acid/Base Epoxide opening

  1. Acid: NaOH in H2O

  2. Base: H3O+ in H2O

  3. product will be trans

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Synthesis of Glycol with Dihydroxylation

  1. OsO4 in NMO/H2O

  2. cis product

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Reactivity of Glycols/Diols

  1. H5IO6 OR HIO4 in HOAc

  2. cleavage

  3. must be a syn diol because undergoes cyclic intermediate