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Rec_2key - Recitation Problem Set#2 CHE-M 1521 1.f l 7ft 8...

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Unformatted text preview: Recitation Problem Set #2 CHE-M 1521..- 1 .f' l 7ft) 8 1) Explain why a single pure product is obtained from the hydroboration-oxidation of 2-butyne, whereas two products are obtained frorn 11ydroboration-oxidation of 2—pentyne. (Bruice — page 265)Well _,__..—-o ,__.‘:.“____ HZFW 63%; fth- LKE‘AS’TAQ - “E ., /fi\/” /’§\\x’f\ Jr /"/\fi/ x‘ . O awe gidvx «35M? 6:33;» 2) What will be the major product of l-propyne with each of the following reagents: (Bruice page 263) a) HBTU moi) b) HBr (2 moi) c) Aqueous stoirngsot d) Disiamlyborane followed by Hzogxon' e) Nat-NH; f) NEINHQINH3 _E: 41* i4 /°~': I m n 3) GIVE two sets of a conjugated diene and dienophile that could be. used to prepare : ' — ”2 (B J 7’") IO OarLH? _ _._"- _ ..- _._ = / I ' l: + m Bl Resale an “we __d __. .____ CH3 Recitation Problem Set #2 CHEM 152L 1/17/08 4) Which diene and which dienophile could be used to prepare the following compounds: (B-327) CI CN 0 o 0 CH3 / / / t“ / a \ \\7 CK/ ¥ 6 .L \\\ \ ?\ \\ \ \— \ 0 LE/ |C\\>r 0‘3 ”\1 -\- ‘ \ n/ 0‘5 0 5) The following equilibrium is driven to the right if the reaction is carried out in the presence of maleic anhydride. What is the function of the maleic anhydride? 0 CH3 CH3 CH3 H30 4? Recitation Problem Set #2 CHEM 152L 1/ 17/08 6) In 1935 J. Bredt, a German chemist, proposed that bicycloalkene cannot have a double bond at a bridgehead carbon unless one of the rings contains at least 8 carbon atoms. This is known as Bredt’s rule. Explain why there cannot be a double bond at the bridgehead carbon. / brIdgehead carbon KEH clog~ Mad ((1qu woufié ken/s \'\3 \Vb SP2 \njégy‘ultud. ”EC“; 6‘3” (>1; \206 0111);)»: ‘l-qul \QfiLXOYkNCch (OUR/K wag l'bO HULK 34m. Comm: w mung Recitation Problem Set #2 CHEM 152L 1/17/08 6) In 1935 J. Bredt, a German chemist, proposed that bicycloalkene cannot have a double bond at a bridgehead carbon unless one of the rings contains at least 8 carbon atoms. This is known as Bredt’s rule. Explain why there cannot be a double bond at the bridgehead carbon. / brIdgehead carbon 7) Cyclopentadiene can react with itself in a Diels-Alder reaction. Draw the endo and exo products. /\ / (DFA \LJ *\\‘ alga / ...
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