2: Reactions to Know 1. Addition to Alkenes - Alkyl halide formation H HX X X = Br, Cl, or I. Halogen ends up on the more substituted carbon (Markovnikov Addition). - Alcohol formation: Markovnikov OH 1. Hg(OAc) 2 (Oxymercuration) 2. NaBH 4, OH H - Alcohol formation: anti-Markovnikov H 1. BH 3 (Hydroboration) 2. H 2O 2, OH OH - 1,2-Glycol formation (dihydroxylation): syn addition 1. OsO 4 HO OH 2. H 2O, Na2 SO3 (anti addition could be achieved through: 1) epoxide formation, followed by 2) epoxide ring opening.) - Alkane formation (reduction of double bond) H 2, Pd/C H H (syn addition: both H atoms add from the same face of the alkene) or H 2 /Pt - Bromo(and chloro) ether formation X2 RO (anti addition. X=Br or Cl) ROH X 2. Reduction of Alkynes - cis-Alkene formation H2 H H (cis product formed) Lindlar catalyst - trans-Alkene formation Na NH 3 H (cis product f ormed) H 3. Cleavage of Double Bonds - aldehyde formation R R 1. O3 H H 2. (CH 3)2S R 2 O H (reductive conditions) - ketone formation R R R R 1. O3 R 2 O R 2. Zn/CH 3COOH (reductive conditions) - carboxylic acid formation R R H H 1. O 3 R 2 O HO 2. H2O2, NaOH (oxidative conditions) 4. C-C Bond Formation - Wittig Reaction R (Ph) 3P=CR' 2 O R R CR'2 ("reverse" of ozonolysis) R - Grignard Reaction R R 1. R'MgX O R' 2. H2 O R OH (f orms alcohols f rom ketones/aldehydes) R - Alkynylation R H strong base R M Base-H (strong base: nBuLi, NaNH2, and etc. M=Li or Na, respectively.) R R' (L=leaving group) L R R' L 5. Oxidation - carboxylic acid formation R Na 2CrO 4 O H3 O+ H OH H H O HO (aldehyde) R R (carboxylic acid) Na2 CrO4 H 3O+ R O HO (primary alcohol) (carboxylic acid) - ketone/aldehyde formation OH R R' Na 2CrO 4 H3 O+ H (secondary alcohol) R OH PCC H H (primary alcohol) R O R' (ketone) R O H (aldehyde) (PCC=pyridinium chlorochromate) 6. Reduction - alcohol formation R LiAlH 4 O R'O R R LiAlH4 O OH R' LiAlH 4 R O H 7. Functional Group Conversion - conversion of -OH into a better leaving group PBr3 Br R OH TsCl Cl R SOCl2 OTs R R O S O (Ts)