Solutions_Manual_for_Organic_Chemistry_6th_Ed 33

Solutions_Manual_for_Organic_Chemistry_6th_Ed 33 - (h) 1...

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Unformatted text preview: (h) 1 -45 continu� F-B - F I F e lectrophile Lewis acid CH2 = CH2 nucleophile Lewis base • F + -I F - f - CH2 - CH2 F + ( i) B F3 - CH2 - CH2 electrophile Lewis acid 1 -46 (a) H2S04 + � + C H2 = CH2 nucleophile Lewis base .. B F3 - CH2 - CH2 - CH2 - CH2 + C H3COO+ HS0 4- + C H3COOH + (b) CH3 COOH ( e) <) + g- O- H + o ( CH3hN: + C H 3 COO� OH ( CH 3 hN + <) (CH3hN: -O-C - O- o g - o2 H20 - H + H20 ( d) (CH3hN - H (e) HO - C - OH (f) oI I - OH 2 -0H HO+ + oI I + H 20 + H20 + N H3 + + NH4 + (g) HCOOH C H 30- HCOO- CH30H 1 -47 C H3CH2 - 0- Li+ + C H4 (a) CH3 CH2 - O - H + C H3-Li (b) The conjugate acid of CH3Li is CH4 Table 1 -5 gives the pKa of CH4 as > 4 0, one of the weakest acids known. The conjugate base of one of the weakest acids known must be one of the strongest bases known. -----l.� 23 ...
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