Example Identify all possible structural and stereoisomers that can result from the addition polymerization of (a) butadiene (b) chloroprene HHHH HCI H H C-C=C C=C-C=C H H H (a) (b)

Name the following alkynes: (а) CH3 CH3 (b) CH3 CH3CHC=CCHCH3 HC=CCCH3 ČH3 (c) CH3 (d) CH3 CH3 CH3CH2CC=CCH2CH2CH3 CH3CH2CC=CCHCH3 CH3 CH3

5:51 Draw examples of the following: (a) A meso compound with the formula C8H18 (b) A meso compound with the formula C9H20 (c) A compound with two chirality centers, one R and the other S

5. (X)C,H¬OC1- NH3 →C¢H„ON- Br2 →CH3CH2CH2NH2; Compound (X) i : КОН CH3 (b) CH3 (a) (c) -HO- (d) cl- CHO Cl

There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17

S: What compound is 5-cyclopentyl-2- methylhexanal? (A) (B) (C) (D) 티 Ele H a H H H H

3. Assign E or Z stereochemistry to the following alkenes: (a) НОСН2 CH3 (b) HO2C H C=C C=C H3C CI OCH3 (c) NC CH3 (d) CH3O2C CH=CH2 C=C C=C CH3CH2 CH2OH HO2C CH2CH3 4. Classify the following reactions as additions, eliminations, substitutions, or rearrangements: (а) CН3Br + KоН — СH3ОН + KBr (b) CH3CH2C1 + NaOH → (c) H2C=CH2 + H2 H2C=CH2 + NaCl CH3CH3 5. Which of the following are most likely to behave as electrophiles, and which as nucleophiles? Explain. (a) NH4+ (b) C=N- (c) Br+ (d) CH3NΗ, (е) Н—С—С-—н

Using Newman projections, draw each of the following molecules it most stable staggered, least stable staggered, least stable eclipse and most stable eclipse conformations with respect to the bond indicated:(a) 4-ethyl-3-methylheptane, C3-C4(b) 4-isoproply-2,4,5-trimethylheptane, C4-C5(c) 6-isopropyl-2,5-dimethylnonane, C5-C6

Which of the following projections would show the second-highest energy conformation looking along the C1-C2 bond of 1-bromopropane? H H Br ,,. (B) (C) ମା (D) OA OB Oc OD OE H Ни 11 HH Br (E) H- H H H Hol,

Name the following cycloalkenes: (c) CH(CH3)2 CH3 -CH3 (a) CH3 (b) CH3