Organic Chemistry Study Sheet

Jun 21st, 2015
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o Regioselectivity depends on the preference of the reaction to proceed through the more stable carbocation. o In many cases, a stereocenter is formed, resulting in the formation of enantiomers in a racemic mixture.

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Organic Chemistry Study SheetThings to KnowSubstitution reactions convert one group to anotherElimination reactions convert alkyl halides or alcohols into alkenesAddition reactions add two groups across a double bondThings to ConsiderAddition ReactionsWhat are the identities of the groups added across the double bond?What is the expected regioselectivity (Mark or anti-Mark)?What is the expected stereospecificity (syn or anti)?Some General TermsMarkovnikov Addition- The substituent is placed in the vinylic position bearing more hydrogen atoms (more substituted)Anti-Markovnikov addition- The substituent is placed in the vinylic position bearing less hydrogen atoms (less substituted)RegioselectivitySyn addition-Addition of H&X across a double bondHydrohalogenationMarkovnikov is achieved by adding pure HX. Anti-Markovnikov is achieved by adding HX with any trace of ROORs. MechanismRegioselectivity depends on the preference of the reaction to proceed through the more stable carbocation.In many cases, a stereocenter is formed, resulting in the formation of enantiomers in a racemic mixture. Carbocation rearrangements will generally occur if they can, via a methyl or hydride shift. Therefore, a mixture of products will form. For example, a secondary carbocation can be converted to a tertiary carbocation. A nucleophilic attack can occur on either carbocation, resulting in a mixture-Addition of H&OH across a double bondAcid-Catalyzed HydrationMost simpl

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