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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.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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.
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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