4- Predict the product of the following reaction and show stereochemistry. (4) lomstud 1- arv Onorogners (1) BH3: THF (2) H₂O₂, HO™

3. For each of the following reactions, fill in the missing products, reactants, or reagents as appropriate. Account for stereochemistry when appropriate. CI Br KCN CH3OH Ph CH3OH (а) (b) CH3 CH3 KO'Bu 'BUOH Br

(c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br H. B + C

(ii) Draw the product R, including a detailed reaction mechanism for the conjugate addition reaction between the 1,3-dicarbonyl P and the a,ß-unsaturated ketone Q. Eto P OEt + Q OEt Et3N R (iv) Explain why conjugate addition is favoured over direct addition to Q in this case.

1) Show the product(s) from each of the following reactions including all stereochemical outcomes. If more than one major product is formed show both, including stereoisomers. If no reaction is expected then write (NR). Br HOCH,CH, HI PdC Brz CHCI, I) BBN 2) N2OH. H;O: CS Scanned with CamScanner

Predict the major products of the following reactions, including stereochemistry where appropriate. (a) cyclooctanol + NaOCl/HOAc (b) cyclopentylmethanol + CrO3 . pyridine . HCl

19) Give the products obtained from the following Wittig reaction. Show both stereoisomers. O || -CCH3 CH3CH₂ Ph .H Y" + Ph -P=C Ph Give the products for the following reaction. CH₂ CH3 K C₂H₂ CH₂ H + C₂H₂ CH3 ?

For each compound, give the product(s) expected from (1) HgSO4>H2SO4@catalyzedhydration and (2) hydroboration–oxidation.(a) hex-1-yne (b) hex-2-yne(c) hex-3-yne

(c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br B + C

The treatment of (CH3)2C = CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its H NMR and IR spectra.