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Solutions Manual for Organic Chemistry (Wade 6th Ed)

Solutions Manual for Organic Chemistry (Wade 6th Ed) - 1...

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1 3-4 1 (c) continued CH DEPT-90 CH DEPT-135 CH CH2 13-42 The multiplicity of the peaks in this off-resonance decoupled spectrum show two different CR's and a CH3. There is only one way to assemble these pieces with three chlorines. Cl CI I I 020-- CH3- CH - CH q t I � CI 075 060 d d 13-43 There is no evidence for vinyl hydrogens, so the double bond is gone. Integration gives eight hydrogens, so the formula must be C4HsBr2' and the four carbons must be in a straight chain because the starting material was but-2-ene. From the integration, the four carbons must be present as one CH3, one CH, and two CH2 groups. The methyl is split into a doublet, so it must be adjacent to the CH. The two CH2 groups must follow in succession, with two bromine atoms filling the remaining valences. (The spectrum is complex because the asymmetric carbon atom causes the neighboring protons to be diastereotopic.)
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