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Transcript
1. Alcohols, Phenols, Oxidation and Reduction Alcohols are names with the suffix –ol The acidity of an alcohol/phenol can be assessed using its conjugate base: Consider Atomic size/Electronegativity, Resonance, Induction, Orbital Type (ARIO) Electron withdrawing substituents stabilize conjugate bases while electron donating ones destabilize a conjugate base Alcohols preparation: via SN1, SN2, hydration, and Grignard (MgBr-[C…]) mechanisms Reduction: H2 with Pt/Pd, NaBH4 and LiAlH4 (more reactive, can be used for esters). Need quenches for NaBH4 and LiAlH4 Oxidation: CrO3, H+/Na2Cr2O7, H+ (Joan’s reagents – strong oxidizers – will lead to carboxylic acid product) and PCC (mild oxidizer – will only lead to ketone/aldehyde products) 2. Dienes, Dienophiles, Diels –Alder Mechanism Diene: has conjugated pi bonds Dienophile: must have at least one pi bond s-trans = more stable conformer, but diene must be able to assume s-cis conformation to participate in a Diels-Alder rxn 3. Benzene Derivatives and Rules of Aromaticity Aromaticity: Cyclic, sp2 at each atom, 4n+2 pi electrons (Huckel’s Rule), planar 4. Electrophilic Aromatic Substitution (EAS) & Nucleophilic Aromatic Substitution (NAS) EAS and NAS mechanisms maintain aromaticity. NAS: Need a strong nucleophile, a good leaving group and a strong EWG ortho/para to the LG 5. Ethers and Epoxides Williamson Ether synthesis: 1. Attack with NaH (:H- = strong base/nuc) 2. SN2 with alkyl halide (has to be 1° or 2° and sp3) Epoxide preparation is achieved with m-chloroperoxybenzoic acid (mCPBA) 6. Aldehydes, Ketones and Nucleophilic Addition Reactions Aldehydes end with the suffix –al Ketones end with the suffix –one Aldehydes are more reactive than ketones because of sterics and electronics (Aldehydes are connected to 1 EDG alkyl group while ketones are connected to 2) 7. Reactivity of Carboxylic Acids, Esters, and Amines and Named Mechanisms Preparation of Carboxylic Acid: 1. NaCN 2. H3O+ or 1. Grignard 2. CO2 Keto-enol tautomers are constitutional isomers Keto = significantly more stable conformer – acts as an electrophile Enol = least stable conformer – acts as a nucleophile NaOH = best base for aldol condensation reaction