Worked Example 8.1 Predicting the Products of a Hydration Reaction Strategy Determine type of reaction being carried out Two methods of hydration Hydroboration/oxidation Occurs with syn stereochemistry Gives non-Markovnikov alcohol Oxymercuration Occurs with anti stereochemistry Gives the Markovnikov alcohol
Strategy ▪ Determine type of reaction being carried out ▪ Two methods of hydration ▪ Hydroboration/oxidation ▪ Occurs with syn stereochemistry ▪ Gives non-Markovnikov alcohol ▪ Oxymercuration ▪ Occurs with anti stereochemistry ▪ Gives the Markovnikov alcohol Worked Example 8.1 Predicting the Products of a Hydration Reaction
Worked Example 8.1 Predicting the Products of a Hydration Reaction Solution CH3 CH3CH2CH=CCH3 (a) 2-Methylpent-2-ene (b) 1.BH3 1.Hg(OAc)2,H2O 2.H202,OH 2.NaBH4 H CH3 H CH3 CH3CH2C-CCH3 CH3CH2C-CCH3 HO H H OH 2-Methylpentan-3-ol 2-Methylpentan-2-ol Cengage Leaming All Rights Raoerved
Solution Worked Example 8.1 Predicting the Products of a Hydration Reaction
Worked Example 8.2 Synthesizing an Alcohol How might you prepare the following alcohol? CH3 CH3CH2CHCHCH2CH3 OH Cge Lamng Al Pg Peerved
How might you prepare the following alcohol? Worked Example 8.2 Synthesizing an Alcohol
Worked Example 8.2 Synthesizing an Alcohol Strategy To synthesize a specific target molecule work backwards Target molecule is a secondary alcohol -OH bearing carbon in the product must have been a double-bond carbon in the alkene reactant Devise a method and select possible reactants Add-OH here Add-OH here CH3 CH3 CH3CH2CHCH-CHCH3 CH3CH2C=CHCH2CH3 4-Methylhex-2-ene 3-Methylhex-3-ene
Strategy ▪ To synthesize a specific target molecule work backwards ▪ Target molecule is a secondary alcohol ▪ –OH bearing carbon in the product must have been a double-bond carbon in the alkene reactant ▪ Devise a method and select possible reactants Worked Example 8.2 Synthesizing an Alcohol
Worked Example 8.2 Synthesizing an Alcohol Solution CH3 CH3 1.BH3,THF CH3CH2C=CHCH2CH3 2.H202,OH CH3CH2CHCHCH2CH3 3-Methylhex-3-ene OH Note:4-methylhex-2-ene has a disubstituted double and would probably give a mixture of two alcohol products with either hydration method
Solution Note: 4-methylhex-2-ene has a disubstituted double and would probably give a mixture of two alcohol products with either hydration method Worked Example 8.2 Synthesizing an Alcohol