ps1 - are equivalent, and have an N-O bond length of 1.21...

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Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #1 FALL, 2009 Please answer problems 76, 78, 83, 92, and 93 in Chapter 1 of Bruice. Also answer the following questions: (1) One Kekulé structure for diazomethane is CH 2 =N=N. Draw the corresponding Lewis structure, and indicate any formal charges. (2) Indicate the most important resonance structure in each series shown below, and explain why. (a) (b) (c) H C H NH H C H NH H C H NH H 3 C C O O H 3 C C O O H 3 C C O O F B CH 3 O OCH 3 F B CH 3 O OCH 3 F B CH 3 O OCH 3 (3) In the substance nitryl chloride NO 2 Cl, both the oxygen atoms and the chlorine atom are bonded to nitrogen. Experimental studies have shown that both nitrogen-oxygen bonds
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Unformatted text preview: are equivalent, and have an N-O bond length of 1.21 Å. [Note: a typical N-O single bond is 1.45 Å; a typical N=O double bond is 1.15 Å]. Use Lewis structures to represent NO 2 Cl in a way that explains these data. Be sure to indicate any formal charges, if appropriate. (4) When formaldehyde, CH 2 =O, reacts with acids (H + ), a new O-H bond is formed. What Lewis structures are possible for this “protonated formaldehyde?” Which Lewis structure would be the major resonance contributor?...
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This note was uploaded on 11/10/2009 for the course CHEM 1570-001 taught by Professor Tadhgbegley during the Fall '08 term at Cornell.

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