DATBooster's Organic Chemistry Reaction Sheet

DAT Booster Organic Chemistry Reaction Sheet Substitution and Elimination Reactions SN2 reactions - Bimolecular substitution - Less steric hindrance of substrate makes reaction faster. SN2 is good on methyl and primary substrates, okay on secondary substrates, and NR on tertiary substrates. - SN2 causes inversion of stereochemistry. - Polar aprotic solvent (DMSO, acetone, THF) favors SN2. Polar protic solvent engages in hydrogen bonding and decreases reactivity of nucleophiles. - SN2 requires a strong nucleophile (N3-, CN-, HO-, RO-). - Pentavalent transition state with central carbon being approximately sp2 hybridized. - Rate Law = k[substrate][nucleophile] Mechanism: E2 reactions - Bimolecular elimination - E2 occurs on primary, secondary, and tertiary substrates. - Leaving group and H atom must be anti-periplanar (pointing in opposite directions). - E2 requires a strong base (HO-, RO-, H2N-, R2N-). - The Zaitsev product (more substituted alkene) is favored in the reaction when the base is small, but the Hofmann product (less substituted alkene) is favored when the base is bulky. - Polar protic solvent (H2O, ROH, NH3) and heat favor E2. - Rate Law = k[substrate][base] Mechanism: SN1 reactions - Unimolecular substitution - SN1 reaction requires a weak nucleophile (H2O, ROH). - Rearrangements are possible due to carbocation intermediate. - Polar protic solvent favors SN1; hydrogen bonding from solvent stabilizes carbocation intermediate. - Rate Law = k[substrate] Mechanism: E1 reactions - Unimolecular elimination - E1 requires a weak base (H2O, ROH). - Rearrangements are possible due to carbocation intermediate. - Polar protic solvent and heat favor E1; hydrogen bonding from solvent stabilizes carbocation intermediate. - The Zaitsev product (more substituted alkene) is favored in this reaction. - Rate Law = k[substrate] Mechanism: Alkene Reactions Catalytic Hydrogenation Key Info: syn-addition stereospecificity; no regiospecificity; no rearrangements Acid-Catalyzed Hydration Key Info: no stereospecificity; Markovnikov regiospecificity; rearrangements are possible; carbocation intermediate Acid-Catalyzed Addition of Alcohol Key Info: no stereospecificity; Markovnikov regiospecificity; rearrangements are possible; carbocation intermediate Oxymercurati on Demercuratio n Key Info: anti-addition stereospecificity; Markovnikov regiospecificity; no rearrangements; mercurinium ion intermediate Alkoxymercurati on Demercuration Key Info: anti-addition stereospecificity; Markovnikov regiospecificity; no rearrangements; mercurinium ion intermediate Hydroboration Oxidation Key Info: syn-addition stereospecificity; anti-Markovnikov regiospecificity; no rearrangements Syn Dihydroxylation Key Info: syn-addition stereospecificity; no regiospecificity; no rearrangements Syn Dihydroxylation Key Info: syn-addition stereospecificity; no regiospecificity; no rearrangements Anti Dihydroxylation Key Info: anti-addition stereospecificity; no regiospecificity; no rearrangements Epoxidation Key Info: syn-addition stereospecificity; no regiospecificity; no rearrangements Halogenation Key Info: anti-addition stereospecificity; no regiospecificity; no rearrangements; bromonium ion intermediate Halohydrin Formation Key Info: anti-addition stereospecificity; Markovnikov regiospecificity; no rearrangements; bromonium ion intermediate Haloether Formation Key Info: anti-addition stereospecificity; Markovnikov regiospecificity; no rearrangements; bromonium ion intermediate Hydrohalogenation Key Info: no stereospecificity; Markovnikov regiospecificity; rearrangements are possible; carbocation intermediate