ACS Organic Chemistry I & II Reactions Reagents, and Functional Groups EXAM GUIDE 2024

Alcohol - Ketone - Amine - Ether - Amide - Ester - functional groups - Alkyl - An alkane missing a hydrogen Aromatic compound - Cyclic, planar, with every atom of the aromatic ring having a p orbital, while obeying hackles rule of 4n+2 pi electrons Vinyl - Hydrolysis Reaction - Carboxylic Acid - pKa ~ 5 Enantiomers - stereoisomers that are non super imposable mirror images Diastereomers - - Same molecular formula, same bond connections, NOT mirrors images, NOT the same compound. Stereocenter - sp3 hybridized and bounded to different subsitutents Chiral - objects with non-superimposable mirror images; 'handedness' Meso - Achiral compound that contains stereocenters Cahn-Ingold Prelog - R/S Nomenclature E2 - 3⁰ with strong base, 2⁰ with strong base, 1⁰with strong, non-nucleophilic base E1 - 3⁰ with weak base in polar, protic solvents, 3⁰ in polar, protic solvents, with poor nucleophiles, 2⁰ with poor nucleophiles in polar, protic solvents SN2 - 1⁰ with strong bases, 1⁰with weak bases, 2⁰ with weak bases SN1 - 2⁰ or 3⁰ in weak bases or poor nucleophiles in polar, protic solvents CH₃OK/CH₃OH - Favors SN2 or E2 Acetone - SN2 OH⁻ - Nucleophilic Displacement Reaction Nucleophile - Electrophilic Additions - Attracted to C=C because of it being oxygen rich Forms a carbocation intermediate that rearranges to a more stable carbocation that is immediately susceptible to nucleophilic attack, completing the addition to the double bond. Attack is on most stable carbon. CH₃OH/H⁺ - The H⁺ attacks first. The oxygen of the methanol is the nucleophile NaH - ROH to RO- Na+ NaBH4, MeOH - Ketone to alcohol H2/Pt - Reducing to cis 1. LAH 2. H2O - Reducing to trans 1. RMgX 2. H2O - Add R group TMSCl, Et3N - Protection group of alcohols TBAF - Remove alcohol protecting group 1. TsCl, py 2. NaBr - Make water good leaving group. The sn2 SOCl2, py - Chlorination of alcohol H2SO4, heat - Elimination -OEt - Elimination Jones - Secondary alcohol= ketone Primary alcohol= carboxylic acid PCC - Primary alcohol= aldehyde 1. Hg(OAc)2, H2O or ROH 2. NaBH4 - Markinov addition MCPBA - Epoxide ring