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Homework 3 - Homework 3 Fall 2009 1 2-chloro-2-methyl...

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Homework 3 Fall 2009 1. 2-chloro-2-methyl pentane reacts with sodium cyanide giving two products: A. 0 1 2 3 PPM 6 3 2 2 C 7 H 13 N IR : 2200cm -1 B. 0 1 2 3 4 5 6 PPM C 6 H 12 1 2 3 3 3 IR: 1605cm -1 Write the reaction and identify both products. 2. 4-bromobutanol (spectrum 1) reacts with strong base (KOH) to give a product (spectrum 2) Spectrum 1
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HO Br 0 1 2 3 4 PPM 1 4 2 2 Spectrum 2 0 1 2 3 4 PPM 4 4 C 4 H 8 O 2. 2,2-dimethyloxirane opens in acidic ethanol giving product A. Identify which peaks in the NMR spectrum correspond to the hydrogens in product A. 0 1 2 3 4 PPM 1H 2H 3H 2H 6H IR: 3450cm -1 3. Starting with methylbenzene and using any monofunctional precursors with 3 or fewer carbons and any reagents that you need to give the product of which the NMR spectrum is given below.
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C 16 H 16 O IR 1750cm -1 0 1 2 3 4 5 6 7 8 PPM 10H 2H 4H 4. Using any monofunctional precursors with 3 or fewer carbons and any reagents provide a synthesis for the product of which the NMR spectrum is given below. 0
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