A B C D Please predict the product for each of the following reactions. Make sure to clearly indicate the correct stereochemistry for each compound: HCI 1. NaOH 2. H₂O 1. NaSMe 2. H₂O 9 10 HBr H₂O* 6 H₂O H₂O* CH2CH2OH A B C OH OH 5 + 1. NaCN 2. H₂O 2. H₂O 1. PhMgBr 1. LiAlH4 2. H₂O 1. NaOEt 2. H₂O D

Predict the major product(s) for all of the 6 following chemical reactions. Indicate the stereochemistry where it is relevant. 6. I. I2 ? CuCl2 C. "СНз Ur goiwolldt odlo does ot ouibooouow adi wll Borhe -2 01okio-8-2 ii) 1. BH3 / THF 2. H,О2/"ОН OH iii) KMNO4 Н.О Cl CI bos ploseeioboi-n Ha iv) 1. Na NH2 C CH 2. H bns tolbs 1. OsO4 OH -? 2. NaHSO3/H20 он vi) НBr ? CPCH ether 4.

Consider the following reaction. SH H. „CH3 но product mixture N(C,Hg)3 , rt X = F, CI, Br, I Provide the structures of all major reaction products. Specify the stereochemistry and state the reaction type leading to each product.

Compound W shows stereoisomerism. Draw spatial formulae to show this isomerism and describe the physical property which could be used to distinguish between the Isomers.

Draw the products of the reaction. Be sure to specify stereo- and regio- chemistry where appropriate

(8) Draw the principal organic product expected from the following reactions; indicate stereochemistry where appropriate. i. Br EIS Na ii. Mel iii. Br- CH, NaOH, CH,он iv. NaOH OH v. Mg, Et,0

Give the structure of the product and/or intermediates of the following reactions. Indicate, where appropriate, both regiochemistry and stereochemistry.

3. Predict the product(s) of the following reactions: CH3 CH3CHCH2CH2CO2CH3 2. Hg0* (a) CO2CH2CH3 (b) 1. DIBAH 1. CH3CH2MgBr 2. H30" (c) .COCI CH NH2, ? (d) CO2H CH,OH, ? H2SO4 но CH,CO,COCH,, ? Рyridine (e) CH3 (1) 1. LIAIHA 2. H30 H2C=CHCHCH2CO2CH3 (g) .CONH2 (h) CO2H SOCI2 1. LIAIH, 2. Нао Br CH3 e2016 Cenag Leming

9. Write structural formulas for the major organic product(s) for the following reactions. Be sure to indicate stereochemistry when relevant. (CH;CH,CH,),CuLi (a) Cl Br PAL2 (b) HO (c) CH;CH,CH,CH,OH C,H5MgBr 10. Propose a reasonable mechanism for the following reaction Be sure to include all intermediates. (transition states are not necessary) Br Br hv CH3-CH=C(CH3)2 + Br, ČH,-CH=C(CH3)2 CH2=CH–Ċ(CH3)2 11. Indicate how each of the following compounds could be prepared using the given starting material CH;CH,CH,CH3 CH;CH,CH,CH,Br CH;CH,CH,CH3 H,C=CH-CH=CH2 Br CH;CHCH,CH3 CH;CH=CCH,CH3 CH3

chem 534 cha Hư OAC H please show stereochemistry H₂ COCH ? H CO₂CH3 O Ac 2. + ? hv 9 40°C 3. H₂ C 4. 0°C Catq Q-0 + [6+4] NGC ?. لك 5. [ V-CO₂CH3 + II NCCN [4+2] C6H5 6. 2 C6H5