PS7_2011Ans - Name Section Rec TA Side 1 of 11 Ch 1b,...

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Name Ch 1b, Problem Set Six SOLUTIONS Section Side 1 of 11 Due Friday, Feb. 26, 2010 Rec TA at 4 PM PST in the Drop Box 1. Nucleophiles and electrophiles (16 points) State whether each of the following molecules will react as an electrophile or as a nucleophile (some a may react as both). Draw the filled or vacant orbital that will participate in the reaction. Solution 2 points 2 points for sketch 2 points 2 points : 1 point each 2 points for sketch 2 points total: 1 point each sketch 2 points 2 points for sketch
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Name Ch 1b, Problem Set Six SOLUTIONS Section Side 2 of 11 Due Friday, Feb. 26, 2010 Rec TA at 4 PM PST in the Drop Box 2. Nucleophile-electrophile reactions (16 points) The molecules shown below are nucleophilic. Identify the nucleophilic atom(s), and draw a curved arrow mechanism for the reaction with a generalized electrophile, E+. Provide the product for each reaction. Solution Sodium ions will dissociate to form carbanions for (a) and (b). 4 points for each part: 1 point: correct identification of nucleophilic atom 2 points: correct arrow pushing scheme 1 point: correct product Subtract 0.5 points for each mistake
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Name Ch 1b, Problem Set Six SOLUTIONS Section Side 3 of 11 Due Friday, Feb. 26, 2010 Rec TA at 4 PM PST in the Drop Box 3. Product prediction (12 points) Complete the mechanisms by drawing the structure of the products in each case. 2 points each: Subtract 0.5 points for each mistake.
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Name Ch 1b, Problem Set Six SOLUTIONS Section Side 4 of 11 Due Friday, Feb. 26, 2010 Rec TA at 4 PM PST in the Drop Box 4. Carbonyl reactivity (16 points) Determine which compound in each of the following pairs is expected to be more reactive toward addition of a generalized nucleophile, :Nu, to the carbonyl bond. Explain your reasoning. (a) 2-hexanone or 1,1,1-trifluoro-2-hexanone (b) Acetone or 2,2,4,4-tetramethyl-3-pentanone (c) Cyclobutanone or butanone (d) N,N-dimethylacetamide or 3-methylbutanone
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Name Ch 1b, Problem Set Six SOLUTIONS Section Side 5 of 11 Due Friday, Feb. 26, 2010 Rec TA at 4 PM PST in the Drop Box Solution 4 points each: 1 point: correct identification of better electrophile 3 points: correct explanation
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Name Ch 1b, Problem Set Six SOLUTIONS
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This note was uploaded on 03/21/2011 for the course CHEMISTRY 1b taught by Professor Reisman;heath during the Winter '11 term at Caltech.

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PS7_2011Ans - Name Section Rec TA Side 1 of 11 Ch 1b,...

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