Solutions_Manual_for_Organic_Chemistry_6th_Ed 76

Solutions_Manual_for_Organic_Chemistry_6th_Ed 76 - 4 -27 R-...

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Unformatted text preview: 4 -27 R- O· J () -0 � H 3C J¢Ct I h 0 R .. R- O ,H ·0 + "TT H 3C II � I l- R CH3 stabilized by resonance­ Vitamin E l ess reactive than R O· 4 -28 The triphenylmethyl c ati on is so stable because of the delocalization of the charge. The more resonance forms a species h as, the more stable it will be. C H3 ( Note : these resonance forms do not include the simple benzene resonance forms as shown below; they are signifi cant, but repetiti ve, so for simplicity, they are not drawn here . ) � +0 ---- +OcO ---- o Oc � b Q= b b /' 0 0 < }-co ---- < }-c ---- o-c ---- < }-c0 + +U b b b+ + � 0 < }-cQ+ ---- < }-cP ---- < }-+c b b b C II 0-+/ _ 'I � Ph ---- C , 4-29 most stabl e (c) + I > Ph ( b) > � 0-+/ II C , + Ph ---- many more Ph ( a) least stable I (c ) C H3 -CCH2CH3 C H3 3° 4-30 most stable (c) . I ( b) CH3-CHCHCH3 CH3 > ( a) CH3 -CHCH2CH2 C H3 1° I + > 2° ( a) least stable . ( b) (c) C H3 -CCH2CH3 C H3 3° ( b) CH3-CHCHCH3 CH3 2° 68 I ( a) CH3 -CHCH2CH2 C H3 1° I . ...
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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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