Make Flashcards From These Notes: Front: Secondary Alcohols To Ketones Back: Naocl/H2o Or Na2cr2o7/H2so₄; Alternatives Include The Dmp Reagent, Pcc, And The Swern Oxidation. Front: Primary Alcohols To Carboxylic Acids Back: Excess Naocl/Tempo Or Na2cr2o7/H2so4 Front: Primary Alcohols To Aldehydes Back: Controlled Oxidation With Pcc Or Dmp Reagent, Swern, Naocl/Tempo Front: Reduction Of Alcohols To Alkanes Back: (1) Tscl/Pyridine (2) Lialh₄ Front: Primary/Secondary Alcohols To Alkyl Halides Back:Hcl Or Socl₂/Pyridine, Pbr₃, Or Pi₂; Front: Tertiary Alcohols To Alkyl Halides Back: Hcl, Hbr, And Hi Work Well. (Sn1 Reaction) For Primary Alcohol It Is A Sn2 Reaction Front: Dehydration Of Alcohols To Form Alkenes Back: H₂So₄ Or H₃Po₄ Front: Industrial Condensation Of Alcohols To Form Ethers Back: Acid Catalysis (H⁺) Front: Cleavage Of The Hydroxy Proton - Tosylation Back: Tscl Followed By Pyridine Front: Deprotonation To Form An Alkoxide Back: Nah Front: Williamson Ether Synthesis Back: Alkoxide Ion (From Alcohol) Reacts With A Primary Alkyl Halide Front: Fisher Esterification: Back: Alcohol+ Carboxylic Acid=Ester Front: Esterfication With Acid Chloride Back: Acid Chloride+ R-Oh Front: Adding Cl To Primary Alcohol Back: Add Zncl2 To Speed It Up (Sn1 Reaction For Tertiary And Secondary) Front: Stereoinversion And Retention Back: Pbr3 P/I2 Are Stereoinversion While Socl2 Is A Retention Of Sterochemistry Front: Diol Reactions With H2so4 Back: Ketone Formation, Methyl On One Of The Carbon Gets Shifted Onto One Of The Other Carbons Front:Diol Cleavage Back: Hio4 Cleaves Diol Into Two Ketones

Secondary Alcohols to Ketones

Secondary Alcohols to Ketones

NaOCl/H2O or Na2Cr2O7/H2SO₄; alternatives include DMP reagent, PCC, and Swern oxidation.

Primary Alcohols to Carboxylic Acids

Excess NaOCl/TEMPO or Na2Cr2O7/H2SO4

Primary Alcohols to Aldehydes

Controlled oxidation with PCC or DMP reagent, Swern, NaOCl/Tempo

Reduction of Alcohols to Alkanes

(1) TsCl/pyridine (2) LiAlH₄

Primary/Secondary Alcohols to Alkyl Halides

HCl or SOCl₂/pyridine, PBr₃, or PI₂

Tertiary Alcohols to Alkyl Halides

HCl, HBr, and HI work well. (SN1 REACTION)

Dehydration of Alcohols to form Alkenes

H₂SO₄ or H₃PO₄

Industrial Condensation of Alcohols to form Ethers

Acid catalysis (H⁺)

Cleavage of the Hydroxy Proton - Tosylation

TsCl followed by pyridine

Deprotonation to form an Alkoxide

NaH

Williamson Ether Synthesis

Alkoxide ion (from alcohol) reacts with a primary alkyl halide

Fisher Esterification

alcohol + carboxylic acid = ester

Esterification with acid chloride

Acid chloride + R-OH

Adding Cl to primary alcohol

ADD ZNCL2 TO SPEED IT UP (SN1 REACTION FOR TERTIARY AND SECONDARY)

Stereoinversion and retention

PBr3 P/I2 are stereoinversion while SOCl