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enantiomer OH CH3 chemistry and stereochemistry of the hydroboration-oxidation sequence. s is a classic problem probing the regiochemistry and stereochemistry of a ce, Hydroboration-0xidation results in theanti-Markovnikovs addition of water to the s that the hydroxyl group will become bonded to the carbon atom that would be the least two steps are stereospecific and result in the syn-addition of water to the double bond. me droboration step in this problem is an isotopically labeled diborane, where the normal en replaced with a deuterium atom. In the hydroboration step, the boron becomes bonded to would form the least stable carbocation and the deuterium atom becomes bonded to the carbon rm the most stable carbocation. The choices provided for this question represent all possible egiochemistry and ry. Choices (A) and (B) have the correct stereochemistry for (C) and T) have the stereochemistry for anti-addition. Thus, choices (C) and (D) ereas choices ed. Of choices (A) and (B), only choice (A) has both the stereochemistry for Jyn-addition and the y for anti-Markovnikov addition of water. Choice (A) is the correct answer. The addition can occur ide of the double bond, producing is involved in the reaction shown? (A) C-C-Cl (B) -c-c (c) c-c- Cl (D) C-C-Cl Knowledge Required: Formation and reactions of carbenes with alkenes. Thinking it Through: The r reaction conditions are rather specific for this reaction and-probably must be taken account. The tert-butoxide is a sterically hindered strong base. When trihalometha nes are treated carbene. The dihalocatese adds to the th the strongbase, deprotonati ion gives the trihalomethyl anion, which loses a halide ion to give the neutral alkene in a cycloadiuon reaction to give the dihalocyclopropane. The cyclopropane. The acidic nature。 tic, with the stereochemistry of the alkene maintained in the the three chlorine atoms on the negative charge of the f the hydrogen atom in the CHC, can be predicted from the stabilizing effect of doice(A), dachlorocart ene. The oter choices are structurally implausible trichloromethyl anion. The loss of a chloride ion leads to waiaie. Show the full mechanism
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The reactien is qclopropanation Yeactien CCHE) acs as an acued thsands the lase o (potassium tert-larbsid CD K H-C-a Me e ,di

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