Solutions_Manual_for_Organic_Chemistry_6th_Ed 48

Solutions_Manual_for_Organic_Chemistry_6th_Ed 48 - ( i) s p...

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Unformatted text preview: ( i) s p 3 _sp 3 I � OJ � - < o,, � � � f"' ; H ___ s p 3 _sp 2 sp 2 -s sp 2 _ sp 3 2 -29 The second resonance form of formamide is a minor but significant resonance contri butor. It shows that the nitrogen-carbon bond h as some double bond character, requiring that the nitrogen be sp 2 h ybridized with bond angles approaching 1 20°. . \ H / C � C / C � 1 20 ° �H / � ,,\\ S p2 -S 'H H sp 2 I 1 09° C II 1 20° + 22 --- sp -sp p -p 2-30 H-C-N-H I H :0: II ° ° H-C=N-H I H : 0 1 °° ° ° + / ( a) The major resonance contributor shows a carbon-carbon double bond, suggesting that both carbons are sp 2 hybridized with trigonal p l an ar geometry . The C H3 c arbon i s sp 3 h ybridized with tetrahedral geometry . H-C-C-C-H I I H H � nor � : R: ..I-----;. .. . � sp 3 / 1 H-C-C=C-H I H H m�or � ?� Sp 2 (b) The major resonance contri butor shows a carbon-nitrogen double bond, suggesting that all three carbons and the nitrogen are sp 2 h ybridized wi th tri gonal pl anar geometry . H-N-C=C-C-H I I I I HHHH minor + .. .. H - N - C - C = C - H .. I I I I HHHH minor •• + • H-N=C-C=C-H I I I I HHHH major + 2 -3 1 In (c) and (d), the un shadowed p orbitals are vertical and parallel. The s hadowed p orbitals are p erpendicula; and hori zontal . ( aJ H 3C ,,, H 3C "- M Q\2 ( bJ .N nK h�V � (d) C H3 _QOYoQ?o O[Q[J riJJ ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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