Solutions_Manual_for_Organic_Chemistry_6th_Ed 220

Solutions_Manual_for_Organic_Chemistry_6th_Ed 220 - 10-9...

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10-9 continued Nitro gRoup at posITIon 2 :0± ±0± Nitro grouP at position 3 :0: ±i²ro grou³ At ´osition 4 :0: . ± .. ±0± ±0± Nitro at µosition 2 DelocAL¶zes neGAtive chArGe. NitRo at µosition 3 cannot de·ocA¸iZe neGAtive charGe At µosition 2 Or 4¹ no resonance stabi·iZationº ±0± NitRo At µosition 4 de·oca·iZes neGative cHarGe» - •• ¼N , .• ± ±0' + ½n¸y when the nitro GRouµ is At one of the neGAtive carbons wi·· the nitRo hAve A stABi·i¾inG effect (via resonAnce) º ¿husÀ 2Ánitroµheno· And 4Ánitroµheno· are substAntia··y more Acidic thAn µheno· ÂtSe¸fà but 3- nitroµHenoÄ Ås on¸y s·iGHt·y more acidic than µheno· Ædue to the inductive effectÇ. 10-10 ½È A ÉaÊ Ëtruc²ure A is a µheno· Because the ½Ì is bonded to a BenZene rinG» Ís A µheno·À it wi·· be aciDÎc enouGh to react with sodium hydroxide to Generate a µhenoxide ion that WiÏ· Be faiR·y so·Ub·e in wAter»
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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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