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chem_118b_quiz4_key - CHEM118B QUIZ 4(MONDAY LABS O8/31 1...

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CHEM118B QUIZ 4 (MONDAY LABS –O8/31) 1) Write down the major product of following reaction (20pts) COOCH 3 HNO 3 H 2 SO 4 COOCH 3 NO 2 2) Explain question 1 by resonance structures? (25pts) COOCH 3 O N O COOCH 3 NO 2 H COOCH 3 NO 2 H COOCH 3 NO 2 H Better resonance structures can be drawn for nitration at the meta position. Also take note that the ester is a deactivating group that directs the incoming electrophile to the meta position. However, substitution at the para position results in the positive charge next to the already partial positively charged carbonyl (shown below), which is destabilizing. Thus ortho or para positions not preferred. COOCH 3 O N O COOCH 3 NO 2 H COOCH 3 NO 2 H COOCH 3 NO 2 H destabilizing contributor
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3) Calculate the Rf values for the following TLC? (15pts) A B C distance traveled by solvent distance traveled by C starting ppoint retention factor rf. = d i s t a n c e t r a v e l e d b y s u b s t a n c e distance traveld by solvent rf for A = 2.3/3.3 = 0.70 4) Which compound is more polar A, B or C?
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