Chem 124 Exam #2 Reaction Rules (Alcohols)

[H^- Donor] here can only be LiAlH₄ or NaBH₄

[H^- Donor] , H⁺ , H₂O turns Aldehydes into a Primary Alcohol

[H^- Donor] , H⁺ , H₂O turns Ketones into a Secondary Alcohol

[H^- Donor] , H⁺ , H₂O turns Esters into a Primary Alcohol AND the -O of the Ester takes with it whatever it was attached to, becoming another separate Alcohol piece

• [H^- Donor] , H+ , H₂O turns Carboxylic Acids into a Primary Alcohol

• PCC turns Alcohols into Functional Groups:
• Primary Alcohols into an Aldehyde

Secondary Alcohols into a Ketone

• CrO₃ , [Strong] Acid turns Alcohols into Functional Groups:
• Primary Alcohols into Carboxylic Acids

Secondary Alcohols into Ketones

• A Grignard Reagent is an MgBr attached to some series of R groups (ex: CH₃CH₃MgBr)

- Grignard Reagents react with Carbonyls, turning them into an Alcohol AND adding whatever was with the MgBr onto the original carbon that the Carbonyl was attached to

- Grignard reagents can NOT react with Carboxylic Acids (the R group attached to the MgBr just gains a Hydrogen in place of the MgBr when it leaves)

- Alcohol Protection temporarily replaces an alcohol group with a protector (either TMS-Cl or BnCl , Et₃N)

• - Alcohol Protection protects Primary Alcohols > Secondary > Tertiary
• - The Alcohol Protectors are TMS-Cl or BnCl , Et₃N)

NaBH₄ can react with Carbonyl groups EXCEPT for Carboxyl Groups and Esters

(.. so - in other words - NaBH₄ can only react with Aldehydes, Ketones, and Amides then)

LiAlH₄ will react with ALL Carbonyl groups (including Carboxyls and Esters)

The Sn₁ reagents are HCl and HBr

The Sn₂ reagents are PBr₃ and SOCl₂

The E₁ reagents are H₂SO₄ and H₃PO₄

The E₂ reagents are POCl₃ with Pyridine (these two must be together!)