ps6 - O H H(CH 2 4 CH(CH 3 2 CH 3(CH 2 9 disparlure(2 When...

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Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #6 FALL, 2009 Please answer problems 28 , 31, 32, 38 and 44 in Chapter 6 of Bruice, and the following questions: (1) Outline a step-by-step synthesis of disparlure (shown below) which is the attractant substance used by the female gypsy moth to attract males. You may use acetylene and any other compounds containing up to ten carbon atoms.
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Unformatted text preview: O H H (CH 2 ) 4 CH(CH 3 ) 2 CH 3 (CH 2 ) 9 disparlure (2) When the reduction of propyne to propene is conducted using sodium metal in liquid ammonia, the desired product is often accompanied by the formation of propynylsodium, as shown below. Propose an explanation for this result based on the mechanism of the reduction reaction. C C H 3 C H C C H 3 C Na Na liq NH 3 CH 3 CH=CH 2 +...
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