Question 1: Identify the major product(s), starting material(s) and reagents where indicated. Show stereochemistry (syn, anti) or (R,S) when appropriate. a)1. O32. HOAc b)BrCH3OH c)CCCH3CCCH3HH 1. BH3 in THF2. H2O2, NaOHd) 1). 3 eq. NaNH2 / NH3 (liq)2) NH4Cle)BrBrChemistry 333 Fall 2010 -2- Br2 excessf) g)BrNaOEtEtOH Question 2. Propose a series of chain initiation propagation and termination steps for the reaction below. Carefully show the movement of electrons being mindful of the type of arrows (double headed or single headed) that you use. Be sure to show all the products for the propagation steps that you chose. lightRO ORH BrBrH+ ROH Initiation: Propagation: Termination: g)CCl4 hυBr2Chemistry 333 Fall 2010 -3- Question 3. a) A reaction generates carbocation I. CABIHCCHCH3CH2H3CCH3H3CCHH2CCHCH3CH3H2CCHCH3CH2H2CCH3H2CCCH3CH2H3CCH3?? ? What will happen to carbocation I? (Circle one of the following) 1) It will rearrange to A 2) It will rearrange to B 3) It will rearrange to C 4) It will rearrange to A, B, and C 5) It will not rearrange b) In separate reactions, 2-methylpropene (A), propene (B) and ethene (C) are treated with H-I. Compound A reacts fastest. Compound B reacts more slowly and compound C reacts the slowest. Draw the three intermediates and explain the reaction rates. H3CH3CHHH3CHHHHHHHABC Intermediate A Intermediate BIntermediate C Why does A react faster than B or C?Chemistry 333 Fall 2010 -4- c) Circle the most stable alkene and put a box around the least stable: Question 4: Propose a plausible synthesis for any two of the following three molecules. Write DO NOT GRADE on the part (a, b, or c) that you do not wish to have graded. a) HO O b)cistrans c) OH Question 5. Using curved arrows to show the movement of electrons, draw a plausible mechanisms for the following reactions. Be sure to include all important intermediates and draw all resonance structures. a) Cl2CCl4Cl Cl b)