Treatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.
Treatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.SE: Something Extra
Problem 34MP: Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the...
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Transcribed Image Text:Treatment of propadiene (an allene) with hydrogen
bromide produces 2-bromopropene as the major
product. This suggests that the more stable carbocation
intermediate is produced by the addition of a proton to
Br
HBr.
H2C=C=CH,
H3C
CH2
a terminal carbon rather than to the central carbon.
Propadiene
2-Bromopropene
(a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene.
(b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and
consider whether the CH, groups in propadiene are in the same plane.
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