Solutions_Manual_for_Organic_Chemistry_6th_Ed 173

Solutions_Manual_for_Organic_Chemistry_6th_Ed 173 - 8±5...

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8-18 continued (d) Three new asymmetric carbons are produced in this reaction. All stereoisomers will be produced with the restriction that the two adjacent chlorines on the ring must be trans. C l - C l + --G--I< + Cl-Cl .. :Cl: j :Cl: C l CH h r C I l Cl CH3 8-19 The trans product results from water attacking the bromonium ion from the face opposite the bromine. Equal amounts of the two enantiomers result from the equal probability that water will attack either C-l or C-2. Q B , - r <:v H H Q .. 8-20 H20: water will do nucleophilic attack at either carbon from Solved Problem 8-5 H + + equal amounts of enantiomers H enantiomer of product \
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Unformatted text preview: 8±5 the ¶roMoniuM ion shown here is the enantioMer of tHe one shown in Solved Áro¶LeM 8²³ a ²Oo ³H " ",Ch3 0 0 0 ± . ° Ä + _ Å \ H ´µh ² : o ³H ± U > Ch3 .. ¶ U · c h ¸ ¿r Æ \ H ¿r H H from Solved Áro¶leM 8´6: the bromoniuM ion shown is Meso as ¹t has a PLane of syMÇetry; ÈtÉaÊË b y tHe nucLeopHile at the other car¶on from what is shown in ¸he text w¼ll create the enantioMer H ± H Ì¿r Í A', + :Cl: ± "' /²³ ´ H H µ; show PÎodUcts froM I ¶ Both nucLeoPhiLes 0 I ² " ³ ¿r attacÏnG at th³s caÐBoÑ oR ² '¹º H ÄÅ these aÎe the enantioMÒÓs of tÔe stÐuctures shown in the teXt 166...
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