Practice_Problems_for_the_break - CHEM 3045: Intensive...

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CHEM 3045: Intensive Organic Chemistry Practice Problems for the Thanksgiving Break I will provide answers at the end of recitation next week. All of the quiz questions will be from this sheet or from the assigned book problems through wherever we get on Monday (probably through chapter 13, maybe some of chapter 14). 1. (16 points) Compound A , C 6 H 10 , has a proton nmr consisting of 1.71 δ (singlet, 3H relative area); 2.57 δ (singlet, 2H relative area). It has a prominent IR band at 2947 cm-1 and nothing above 3000. Ozonolysis of A produces compound B whose proton nmr consists of 2.09 δ (singlet, 3H relative area) and 2.73 δ (singlet, 2H relative area). B has a strong IR absorption at 1713 cm-1. A reacts with Br 2 /CCl 4 and also reacts with excess H 2 /Pd to give a compound C6H12. Write the structures of A and B and assign the nmr peaks to the corresponding protons in your structures. 2. Compound C , C 8 H 12 , has a carbon nmr spectrum consisting of 2 peaks at 38.7 and 127.6 ppm, which correspond to a CH 2 and CH, respectively. C reacts with 2 equiv H 2
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This note was uploaded on 02/26/2012 for the course CHEM 3045 taught by Professor Breslow during the Fall '09 term at Columbia.

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Practice_Problems_for_the_break - CHEM 3045: Intensive...

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