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    Table 6.2. Acidity of Some Hydrocarbons: Entry Hydrocarbon Cs (CHA) Cs (THF) K (DMSO)

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    This document presents a table showing the acidity values in Cs+(CHA), Cs+(THF), and K+(DMSO) of various hydrocarbons, including benzyl hydride (Entry 1), isopropyl hydride (Entry 2), diphenylmethyl hydride (Entry 3), and triphenylmethyl hydride (Entry 4). The acidity generally decreases down the table. Allylic positions have estimated pKa values of around 45 based on data for propene, cyclohexene, and cycloheptene. The hydrogens on sp2 carbons such as in benzene and ethene are more acidic than hydrogens in saturated hydrocarbons.

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    Table 6.2. Acidity of Some Hydrocarbons: Entry Hydrocarbon Cs (CHA) Cs (THF) K (DMSO)

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    25 views1 page
    This document presents a table showing the acidity values in Cs+(CHA), Cs+(THF), and K+(DMSO) of various hydrocarbons, including benzyl hydride (Entry 1), isopropyl hydride (Entry 2), diphenylmethyl hydride (Entry 3), and triphenylmethyl hydride (Entry 4). The acidity generally decreases down the table. Allylic positions have estimated pKa values of around 45 based on data for propene, cyclohexene, and cycloheptene. The hydrogens on sp2 carbons such as in benzene and ethene are more acidic than hydrogens in saturated hydrocarbons.

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    This document presents a table showing the acidity values in Cs+(CHA), Cs+(THF), and K+(DMSO) of various hydrocarbons, including benzyl hydride (Entry 1), isopropyl hydride (Entry 2), diphenylmethyl hydride (Entry 3), and triphenylmethyl hydride (Entry 4). The acidity generally decreases down the table. Allylic positions have estimated pKa values of around 45 based on data for propene, cyclohexene, and cycloheptene. The hydrogens on sp2 carbons such as in benzene and ethene are more acidic than hydrogens in saturated hydrocarbons.

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    25 views1 page

    Table 6.2. Acidity of Some Hydrocarbons: Entry Hydrocarbon Cs (CHA) Cs (THF) K (DMSO)

    Uploaded by

    panda biru
    This document presents a table showing the acidity values in Cs+(CHA), Cs+(THF), and K+(DMSO) of various hydrocarbons, including benzyl hydride (Entry 1), isopropyl hydride (Entry 2), diphenylmethyl hydride (Entry 3), and triphenylmethyl hydride (Entry 4). The acidity generally decreases down the table. Allylic positions have estimated pKa values of around 45 based on data for propene, cyclohexene, and cycloheptene. The hydrogens on sp2 carbons such as in benzene and ethene are more acidic than hydrogens in saturated hydrocarbons.

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    Table 6.2.

    Acidity of Some Hydrocarbons 583


    Entry Hydrocarbon Cs+ (CHA)a Cs+ (THF)b K+ (DMSO)c SECTION 6.1
    Acidity of Hydrocarbons
    1 PhCH2 H 41.2 40.9 43

    2 (CH3 )2CH H 35.1 33.1

    3 (Ph2)CH H 33.4 33.3 32.3

    4 (Ph)3C H 31.4 31.3 30.6

    5
    31.2
    H H

    6 22.7 22.9 22.6


    H H

    7 19.9 20.1
    H H

    8 18.5 18.2 17.9


    Ph H

    9 16.6 18.1
    H H

    a. A Streitwieser, Jr., J. R. Murdoch, G. Hafelinger, and C. J. Chang, J. Am. Chem. Soc., 93,
    4248 (1973); A. Streitwieser, Jr., E. Ciuffarin, and J. H. Hammons, J. Am. Chem. Soc., 89, 93
    (1967); A. Streitwieser, Jr., and F. Guibe, J. Am. Chem. Soc., 100, 4523 (1978).
    b. M. J. Kaufman, S. Gronert, and A. Streitwieser, J. Am. Chem. Soc., 110, 2829 (1988);
    A. Streitwieser, J. C. Ciula, J. A. Krom, and G. Thiele, J. Org. Chem., 56, 1074 (1991).
    c. F. G. Bordwell, Acc. Chem. Res., 21, 456, 463 (1988).

    of cyclopentadiene, as illustrated by comparing Entries 6, 7, and 9. (This relationship


    is considered in Problem 6.3)
    Allylic conjugation stabilizes carbanions and pK values of 43 (in cyclohexy-
    lamine)11 and 47–48 (in THF-HMPA)12 were determined for propene. On the basis
    of exchange rates with cesium cyclohexylamide, cyclohexene and cycloheptene were
    found to have pK values of about 45 in cyclohexylamine.13 These data indicate that
    allylic positions have pK ∼ 45. The hydrogens on the sp2 carbons in benzene and
    ethene are more acidic than the hydrogens in saturated hydrocarbons. A pK of 45 has
    been estimated for benzene on the basis of extrapolation from a series of halogenated

    11
    D. W. Boerth and A. Streitwieser, Jr., J. Am. Chem. Soc., 103, 6443 (1981).
    12
    B. Jaun, J. Schwarz, and R. Breslow, J. Am. Chem. Soc., 102, 5741 (1980).
    13
    A. Streitwieser, Jr., and D. W. Boerth, J. Am. Chem. Soc., 100, 755 (1978).

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