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Problem 1 The following list includes derivatives of carboxylic acids. Based on what we’ve learned about influences on carboxylic acid derivative reactivity, rank the compounds based on their reactivity toward nucleophiles (1 = most reactive, 4 = least reactive). Briefly discuss the factors you used to determine your ranking. Cl Cl (a) Problem 2 Cl Cl OS O NO O NN OO OOO Boc anhydride O NH2 O ON (b) (c) (d) The Boc protecting group is an anhydride that is very useful in synthesis as a protecting group for amines. It prevents the amine group from reacting and is stable towards most nucleophiles and bases—reagents that amines could react with! Draw a mechanism for the following reaction, which installs the Boc group. Hint: A mechanistic intermediate is shown in braces. NNN DMAP (a base) O O Problem 3 Show an efficient synthesis of the product from the starting material. Show all reagents your need over each arrow, and draw all products and intermediates (do not combine steps). You do not need to show the mechanism for any steps. Please write them from left to right on the page. If you need more than one line, you can draw an arrow, and then continue on the left side of the page with the new structure. There is no need to redraw any structures, simply continue the problem after the arrow. HNO OH = N Boc O Ph3P OEt O Cl 1

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The carbonyl carbon has partial positive charge in an acyl group which is electrophilic in nature and susceptible to nucleophile attack. The extent of electrophilicity depends on the partial positive charge on carbon of acyl group. The resonance effects from substituent with heteroatom act as the electron donor (-N(Me)2, -OMe) and reduce partial positive charge as well as electrophilicity (Fig. 1), so (d) has least reactivity to nucleophile than (c). Whereas electron withdrawing group increases...

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