Oxidation of Alcohols with" Jones Reagent": Primary and secondary alcohols are oxidized by CrO,/H,SO, (Jones Reagent) to form carboxylic acids and ketones respectively; sodium dichromate in acetic acid (Na,Cr0, can also be used CrO3, H2So4 (Jones Reagent) CH COOHIH2O 2° alcohols CH2 CCH.OH Conversion to Silyl Ethers: Alcohols react with chlorotrimethylsilane to form trimethylsilyl ethers which are stable to many reactions which occur in aprotic medium, but can be readily cleaved by reaction with aqueous acid, regenerating the alcohol. This reaction is often utilized to protect an alcohol during a synthesis, such as that shown below (in the synthesis shown, the grignard reagent would react with the acidic proton on the alcohol, destroying the reagent) H HTH2O Chlorotrimethylsilane HO CH3)3 1(CH3)3 1 Mg, ether Ethers, Synthesis& Reactions Synthesis by Sm2 Displacement Reactions: Unhindered primary and secondary alkyl halides react with simple (unhindered)alkoxides by an S,2 mechanism yieldingOxidation of Alcohols with "Jones Reagent": Primary and secondary alcohols are oxidized by CrO3/H2SO4 (Jones Reagent) to form carboxylic acids and ketones, respectively; sodium dichromate in acetic acid (Na2Cr2O7) can also be used. Conversion to Silyl Ethers: Alcohols react with chlorotrimethylsilane to form trimethylsilyl ethers which are stable to many reactions which occur in aprotic medium, but can be readily cleaved by reaction with aqueous acid, regenerating the alcohol. This reaction is often utilized to "protect" an alcohol during a synthesis, such as that shown below (in the synthesis shown, the Grignard reagent would react with the acidic proton on the alcohol, destroying the reagent). Ethers, Synthesis & Reactions Synthesis by SN2 Displacement Reactions: Unhindered primary and secondary alkyl halides react with simple (unhindered) alkoxides by an SN2 mechanism yielding