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Chemistry LibreTexts

6.22: Additional Exercises

  • Page ID
    182921
  • SN2

    7-1 Predict which compound in each pair would undergo the SN2 reaction faster.

    a) FgPDZQ2NIk7NWZ3-jq7z6ozXBR-l22wAEPzuxR4f0kNoYvhhO_BGkfChcpSigYuKsauLK8PTy6EnjjV67RrznL2e6nX0Z5MMvcFqxuDa6pPcXPIRhZeWlY7hZkeQXuFkPXzvsuUW or KcJ2V_Qe7RSynp5z9ChZgyZ20qfogTO1poAS6C1kFNvg2ADKeBy6e-GUVi5tvDXoaZ8AK3l4JV3n6E14smjPKcKy9Bm58-jS7fXNC0lpVx0PZCBB7Fwe4PUP3UkZHL7mm0jMMk3I

    b) kgWUTMjCRpiEU1VMov0XZSgMO8Lq_c5z-wKCivE-DMrmkAvQWzAXL90ufRFMrTeTMltYa92r2WRmgsMQfxD2n0mnWYROFU09yW-xwJWR5s10sjxpf0HB3uehykblgftGaBXdYS1u or FaDTeeyT10P3vbtKNfAic-LDEAa8uVi_G_QsodCU1QnwivvgAfVDiO9bP0DZut5DKwhZcqdta4syanZckrwbs9lBZFqdopwk0sY32SbBEYlkHByUn-D3Y-n1aIYWoil1vHEg-qVo

    c) 3oH7lx5YHKxhnSkr0Btj2QwUrrzNVunDyv82BwrukZZctOBwqAkxXe8OLk1S2t1DkvrzRHUOZVtNXpGcoIJnnDLAQ1dVnYsWgO__0-mbBMs72rhExDl0RFQ5VSnv7b3f_einEGqT or LsxuGEcAxiak53R6Eq9VvvtkJhP6eVsWGYhEA9n3-f8tH_xtVpSNU7EJGGEpkbbZOEGjfT9cFy86IRhyzoW-420mGd3ldi9RYliGfeKOXsGc9CgonEKWqqM3FKm7tcLHI8-iUeT5

    d) F2_G2yGSz7_jpd-76g4bFk8Nk8aoQNXob4APwd6hUF4OSjegHjfNc1IC7zTnf5Oyf1gBrSkEvA_fKg-i_WJiysyBPxOjYx092qHPZ9OA1FWdKxTazi8TFAmXteGQYkmBNjnDxLoV or QSMAE0MdnbrKVl5uiFbchWM2y3uRO4gf7HxulADqx2jOz8XPsmYKOsZYLaf_wFhLcp41-UuOTE_O6v6wYyqPyLCC1YkJLk4cS3iWuOdK_4w4fkvMJ0jeT5VGD3ZG2po5NrU0rDIT

    7-2 Predict the products of these nucleophilic substitution reactions, including stereochemistry when appropriate.

    a) 9uIxg1_jRhOJq8XeghPasGGcHgtQIudh_6s2xl1lIfMUOzhKKkQ82Zs2iOt6uwIM67WaMCpYygkYO2uIJRC2Jgjq5P3l1f_beSJQ6VkiUjeQwM2sFy_NSvx6h3W9hmFLG4qQty_W

    b) -Z-m9rw5HDOj-agUkkI984JLEkNW1sNdr9IlHEF0LFOa0xaD9Cd-pNuzCUigFTsfzj0ftnBRr-TfuyXoMfyibs2-e3tUeEiVH3Jelvuh4joIqe-m-f3TknDUo2ad0OGuWooXWT3y

    c) rAUSDUTLHe144ruI4YhvjGn2nAhNFPHoT8IcZqExneZ_azwJwj8xScRHhlETiu93jRSKmU-jQ5VebsalLBXwTzJ7mkPY0DIMOZzQN_CxLv1FneT1E31EJhgA5-jDffCaGO3GTvnE

    d) 8Q2NwDeLcqxRRwJlKrNVJLDmHxd2D_WdfWHsHFI7ED63QY8ZgfM3g_TN6qEKWyMZuMpWjE96l4-Ka3cewfsP_ddO4-UjqgQhC6u43S1Cxu84fI-mT2yqfx-z9Q8Dl99QEOTqWtbE

    7-3 Show how each compound might be synthesized using SN2 reaction.

    a) PSEdM92RXVLG8f9WGCr6w9Ch04oR2HCSAjw-Pv1_Sm5BuzPopGOHTNEwH84Wwh188B3KCje6YGGMW2vecdN7T-HzKqIhN6a6waTuRq9Nanfiv2BU7N8VXMoxlbyR1i2j8jCvw43C

    b) ZfvxmJ0d-FJsra49pFoCBDSXQg2YcoZ7PNgJs-WEO0Gz5AquIFLcez0bP26YGPjFf9f_odj7SsKBhP1YbuokIAju6NmbM-nGhigWrEiQvVGvJU-WBT-cB_QtCR04oXKMDm0wGMW4

    c) t7atNNoaGnOEWEE9lN_n3N3CRiS6GEDNkDm7hh8s_NnvI3f83GzcsXf3uZyyY-mi8R9c9LevyfYqG0IPWRW5lLczRnAZpnSHZ688DM4iFn-cauSC5-xSjzm1ArN-4szG6InEiF_F

    7-4 Show 2 ways to synthesize the ether below using SN2 reaction

    nOmn_uu94dF8qcp5B-Y9bR_gNMqDCw8At6qa1vgc_Zm-4I5Okh4xceKAQ-MJ5aeYWf7HxcwQVH9S7xerPvRMzQ-lLuNC6i1eBAtkiM4PvNQ3Ba9ZJus6izXCr2CVYhMp4DwNGWDk

    7-5 Of the two ways of synthesizing the compound in previous question (7-4), which one would be the most efficient? Why? Show the mechanism of the reaction as part of your explanation.

    7-6 Arrange the compounds below in increasing order of nucleophilicity.

    H2O; NH2-; CH3O-; CH3CH2O-

    SN1

    7-7 List the following carbocations in order of increasing stability.
    70ZAY1Oo8N9zgCVH8f_204J7xn2CYTP7EiJSex69uwYUA-l6mdb1qTTkF3z5EmJKl82y8DJr9x5c1u1vwSoyUAd8lTsEZ99poxcGNoJzP3Pf6Pc7GU73Jp9phY8L3uCFWVjkYWEw

    7-8 Give the solvolysis product expected when the compound is heated in methanol.

    a) I6gShLpzaERGJTelcylUcCFYslaA3lEQYq0JnT2xuKq6ETuCkadUis0DhCAWrBCmzzgcrt8hhoon5W8oa67K7rww0VBlLG5TYLDiK4a_MXNjUv5FIu0SMtkjM3w_g8hUo0ET9xYv

    b) NFNI3fNyZtKjg8HmdMoGAWROWmFwctkTvSW6I5khnYlOszJ8FW7g_nMB0yUiyX1NBM68gnDbOOBsZ8wRZVoJNHJOnqxq3Mf7qAIhOY2tS9cqy26NH1__EGRX_20XBZK718WrE_uE

    c) 3-anrIOySUwJQ6WRFK4PiZHMSXBxJsz9ZT_udyiEj3xCXD68J2aqr8CyMZAtwajt2eP-LW2PkmkwLEY4gsVmZ_lstS2NkIbwzjLxGDfdLVOFESSkgPLhnGo6_VUndG3WmnJwyZzx

    d) Kmy6y3rblyBQQPZMLdpe71a2mIa7j_d71BCqLE3Gm5FdF0COertJCs7GcsMIUNAFtqP1ResCmMmXq8xf4nSe8qgHJa0VwGbRIo3cixswHr-9wnSOfFeWYnuaQHXIoKcEpbiaMlpr

    7-9 Predict with compound in each pair will undergo an SN1 reaction more quickly.

    a)UfZJTSCBgpzCsDYM6gd08sDbCYm45e1jzNGByLl90uU1pztYFX0iXVF__CX66n5Zf3tKlUrlJHAeAp_Klxpu8cftK8fCgD9BYjYL4xDtcrKcBWFl9lge1o_mjCzpzupsVsaj61mR or NThO9gTRkBKErQCgIFUyYEgtaocNWO6D0V4fR-W76n77aO58NGN5XQMqT6bcUxPc2RMcDk6cIDMYwRab4lbq5acoDivzzBuCPPnlaPjWE82Vlc814Ny5VbgjPMR8d6LDUgUrroB-

    b)COVxnuij75Na2h0dhJciXqbhFX95WWZ1ebh0e4kmqwucykPqHfI1QmM5zVV5fT-Uv99KJrpQETeeXd63gwukZzKBBcBD5FA1pYPW72H0MK2o4YkbOct_DQxWW1eKvXc23fBtLpIP or y8wE2dBaq-Y33eDUanWPvAYTD3wM3pvGF8Sg7Q-7CMapHX-fJxhjntXmoX0oS7MT4xcc0gGJEUxjkmH3M4rtnt4Y99w709sEYyfLUPuvZyHSTe6Z8ORwV41OACUUFUd22V_Cqv6P

    c)T0oatB8jfmwwuNf_jWVT9E-oGCTbzD9jmgo7HcvknLRFkT2ZwXdzPW5RY8r1bFnwH7gYYH-R7YwF8emiNbTAzH-VxOsdXvUrBv17JG2iG956oFGijbSHzl-5iwLbwElTOafh1P-I or d0uC_j7hLKH6N-cNy3DWXI2ytQVPiyrKfy9rx3N46hgLrXc-YJQqZY2KbmHlX4ap55wmO-KxSbJeYw_gQl3yBEShPZw-ClFHwoQR6IFeSN97OMzocSM7ErKYEArRYE31w5tmJHbh

    d)Ff3R9lQBNPmXcwMhG8Ee7-cOGI-dQQNfUbo4MrVtNk41RDhPifxY8EJ6wuGtPF2J4HBprlsfh4Bur8skivPnbfLhD4RqUAEToMNlpDo6MoQDSnKfs06r_btFyEIRhNVsC5nFMY6c or i1CbP6kS2XnilTw_brfHkGrBCT2ZkQmqRoc328nxyPqsuRm6FtpKRs-rOXZzJn60KdqCQDNCIIWAAwu7p083dDNoW157tdhTMKxwj_Jk9SsOTgxefnQdkftWO-vqBcGWlL4DJNBH

    7-10 Show how the following carbocations would rearrange to become more stable. Draw the mechanism of the rearrangement.

    a) E6d1O6rXuYhMMNebW1ui_OR0Pi-taA6hVjp3mPwdmWxwZC-19ogEjQKI46PGtaoZO8TCqHwsxawxqaamPfofxrOuppS5ZxUI50beWmYufNqM7b1PS6pXNqnrGT3R1ZF_sbK2sFin

    b) 3lzcCZrYQBEIsUNihsWPbz1CLVBZ7STpsYed3eJoa9N-3ezbYF8UUfcknwxPnSg0wIX_TpLpWItfMug7-c2foTYWxd3kBCPJuPB22mZo8QbCrLfbB86vLteO3ejXTVlK8WKdE-oo

    c) 1zJvlQ0GOefnaqu8QTsoaePzH9RVa_Pf8HbRxEuILW9fEXkvXIAYx1mXHss1f3dQhGOlG-VccuYFKPhj5QHxOf8a-hYJFt4OZalfAG3yr0ShgsSuvb-BgOZAeUUlbvzxEgzJp97M

    d) ILF8_lqnCvMaWXqPaa7cNMif3pJl-olZbkQ-0reW9cOekvDP4_0LIF2sBBx2KgWFotDyyDAPLVD4osZYAo8ASodLWEmxtf6jIX9K1ev6uWmqk9uoD3uduQ8J7WG-5wRHffqZFOO6

    SN2 vs SN1

    7-11 Predict whether each compound below would be more likely to undergo a SN2 or SN1 reaction.

    a) C4VhBR2_CVmTYUnbWBk1_g2kpv3too9xEqu0lFRAIz-YZMeJ8Cxg_M9isJFxBgQUDacmu9pTRFrepWUeHL7Rt-V6-sMJ2MIriJqLaiy-C60Kd0ySl6399ZDmKcOjc-Dp5DQTcq6k

    b) 1a7gpg89DTW1B7JN4M98prbNo3xxA8F-AJWIM8rlygCqFylNN6Bji5ctLazRLFLTfsaBKKYgw-a9k7EcmgjtNVYNMHBbksH5y-BheQHUf6Cxt34G5Amhfza6AWZnEeSuEdDSLnCU

    c) aXhgHZEqq2FQg8e9NKK5s2telC3W3TZn0RQSyrnekJg_dNVpaYDb3rWVPWrplNf4uFG6EXaR6sFhv6AcYhOmQu6DK3jM2eZT1xkha3bC0qA4LBeaKdUbeXhvdN4L1bHX1VqmO-8T

    d) 5q_WZJ0ACQ00k0yh5iWES0ggnZfTGyzjyL-MLwitQSgscRW1p1MTW6TsaLpqcr1Oi1F1b9CTYEdn2u6x5SHrGEhNDUSOoIfZZRRy4xU86yIySIrZg1FkDdnTWsVrrmytgHbLZ5m-

    7-12 Predict the product of the following reactions.

    a)KoswwJMmR-9SzKPyT9fcD7IU0t1gmLCYU3Qz9cRhH0xsuTdNdac0dqmGBimEbIdpa6lwf6ox-_8Y6_3wWIs4GxikMikJsO4Zp5LReFPWJkkpPvxCPy8LqZzg8n3FsQQN1817uziP

    b)y4hfRUcza_xxz1Em72FWOdqPLQt9wctSaXXw7YVOciTUDdrix_t-fH4yFFfi4lcRBpGs9EA192mreQ1AFGwF-5jOV2Yx9p5jDRGDJSUZHjFVJaiT__CvRkWjC5pwwX48TEBD4iPV

    c)53wKJgAJJ78Z_Djnds6Tcc8tO4EZyRHlVZOLfJzZf72LQDgm21X5-m7tXzOur5xKPrbEIquVZdc3BiWM0924kRYrCROTOwXt-MO2S75WIATRRXqzM8s5uyq1r6vTlnEgBjM6Rs8A

    d)DXanp6lBNNaFhxRQkxmwMJcqfS8plLqrYXMhn8M6YY_gFfvLZaA9VEKS4sXpDAz60xudbQ9qbBL46H0oWtY8dMexx3A0wBlFe5rilQOQNWcqEshHXzUvsCU8byNn3pw6WTU2d0FM

    7-13 Show how each compound may be synthesized using nucleophilic substitution reactions.

    a) ixnnK0Vd6ICr6cWvD4nU4UMLE0lT4ELIuLP5-HpOAT0stLSQNhaUfpD0ujSN2Tsxj1WTNnKANtJsWi8zEkLICa2H3hJJGBz7Zx5io0ub6eu9KDTi_kU-GdnmD1m4al20KC2LtzyH

    b) bjykIljSbs8YrM2XrOQr41RWKVHA7LfU-vfhWgJDXRtio-WJCXHDH7HT02VW3mpyE7ddY6sIxTaOBINahI8rcmHNTDk6uv_O3zA0n2N6iFXrp7VFvnWjEr8_SJ3pblW8SC-gq8XJ

    c) zl2ar53AGJswz6Ghq36ddRt6rbRDPemqEAJ3YlKgWTRF-48SdjH6THQ-QVFWeMrFyChyqIVhPoxhOUdjSlHUh4KPBsLHFecCOeB3b8OuAKIUh3uIwiHoNV6Ed6YpTZUbf7x8CVTy

    d) BTbOPLzNIuDCy_m2PzYaxKUv3ZO5NuEHvqAUx6vQrsp0qXlMevJa196BdOgb4dn0AeF93q0ayuqfkfDTm6wvEg1gvJAw-3ZOXfy2WVd27tauUDeWGHlffADOw_yEkQzCkSNNAG2e

    e) CUwZ956CdCqqqijVlkz2aUlj6g-QvZbHFP5QNw_gBZ_8_Ee08uJHKrnP4Chb1UZy5mbcgCzz2ylOLhZAEbFytEV4ckKVdOg-xTawXnMrjWFEVE32XcUEvhwct6qTFVoWuLMMNb9E

    f) NuVUZsfVIr_sUuiuPnkzH3nmE-PaxhmFK5ug05efXuefoKSKAgmrlRhpnb-nshPaCUexmNEjrmGZpZuHco4FTG8m02shWYK0dU_S9mvoYKO5c7VJeLTq3EXiObnYMg9DAtzGiQQX

    g) 37mqZDxMAycnweJWaW70hT-_AcM4-3B3ANB4jUevTOuw4p8Y9vE3tz3gUqQb4slIO6ys3eiU512ezAx8afq9TffKja0K06W-U2vNnE9GkkwkpuCVWN5QjzKhvDtu9DXbQXryxwKz

    E2 vs E1

    7-14 Predict the major products of the following reactions.

    a) g5U8ZxvPWrZCAUjsHNDVKu3QnGt5eHvUEa75Jljif49TtSqFfmK1SlXFCfbAqYhx-edGYzuKmzDhGyRqpFtaHWXgsSY-2ZGrU6NCTZdQeBfY_s88W_QsalIhOEJ-qJpp5ZzxMUyp

    b) 62WrhkE6AboEjHbWWtNuxALLb27PPymOFH5enrQKXI8GpMKrBg5dCRljbqGnHQy8H1NgO-aqbiqJLdiHJgFOh2DfjfNFQYz2hdLWX96VU5fuMkngCueE9XLhIlJO9Mvndofu0xvE

    c) tJnpX_rYEt--meM9HeybLFJ3xLUEEN2xDIEl11RHsOl6jIJ-VgXU0hpUjF8CiNxKhZILyVins8z5sVbnazHJz05Oru2JoSW181dVRKRkK67q4ZYvTbHk_0iBnxhKNYQBYJIrhKOw

    7-15 Draw the expected major product when each of the following compounds is treated with hydroxide to give an E2 reaction.

    a)G-utTkogTs7YCVoLNOOs-BbdmQfRlzlkcyxznoFwdVtG8ylvbxSQ1WiQmM0TugBmAmF4_i4DpA66Y1Z-PlGaXR7i_ejFKBdn0ikBrStoLTxsbbjoyGRlMsv18ZS54lnsWr4H1Qu7

    b)7PCwE-egj0mH5wS6yVNExWK7JJncmyMTyx_XdYXIWnVu649jjCWVfROlwuP9Mrlv6B_Lt4SUGv1kBNUMp4SyS_gEIOtg4h8g-0lnYFn4iW_AcHHplkSl3xWSQ5rP1DjLNKO66Mv6

    c)1knj2e3ef0G6c5QWexqxM1yHOtk5Q2AfW2G_VZYzgib_2oKIwaYzT1CQxqkkGGguEX7fJXN-clQPkTfgSV5i51GrNXZ6Vk6334GrbeAq2JMz5Lkib7PVlohlkkex1rEGhQaFVfUW

    7-16 Predict all the elimination products of the following reactions and label the major product.

    a) iwyXfNvWRAXnUv-JczNWLyDHfLQv8mcU1qRivLzVX_vXuoprUA3-FSPQSYxzNKscAESoRCNXk7vNXEHrmIQepshZpk_eu4UGIbE0WuMLQEddXr-yYZPOQlVxPwmWS1bDt-4NqD5g

    b) S4b1iQClptfQb9IdTalBjSsWEUbJTJXQuJMkuuz2K1n4KxTKStnq1liQLNEbSZBLkBWpDfNED8KACndPyF2b_0fuXhHwPC8yynXeMhiCiM_4E9V11VI0chjI1yFz6cQXKL2zdVLd

    c) edqv8zurihShXVnyAduQdlqTpAsYMF4YcOZbFkdJ1YPr0xeCDf5WzqgX75IatK-L7FB3DMS1D18LyrM7dP7h0yo68qr8NaLxK3AEowQwYkjLuGqsIGfOBltEuNQAsknluNoVvq5r

    d) QZGVB_-pfbfzCMnWgu7x44S5Vcc79_K-E4YuxP9SRBOb_twhqVMc7rUo-JsUtL34urPzxCanI0SxA3V0VIuNI7bkXKBhU7shbcK4A0AVSKSf_9dxwl62zKJxm6SxxiZ-oSE9cFFX

    Substitution vs Elimination

    7-17 Identify the function of the following reagents. The reagents will be a strong/weak nucleophile and/or a strong/weak base.

    a) Cl-

    b) NaH

    c) t-BuO-

    d) OH-

    e) H2O

    f) HS-

    g) MeOH

    7-18 Identify which mechanism the following reactions would undergo.

    a)Rdo2XrKQ2hw6TcbSepKx6CM8c3Kr146NiL2gwWKhP3cidu3Si0YbR1i-wquDkoGYyLFx9W7HMqagkBLqILTYBhrwOl4OWHTMZbCYcmH8zNA3LVnuVpFSdwqw-Whzl2gGp9afjkDU

    b)e-W8kFVYj5Fhx3nl9EmLcpkDEG_DX4taVcdt8kBlz69JL0mWyWI5GIAlF4ql0XZtDaw5pXb-wZqqI_Fd-7FjRaJAkgEkPr849g2oZBwqJ2xakrmtd5rImd2cjp0FoNGhNXU_L4_t

    c)lPOjennqKsaCzlxzhGs8nqIkCXaYCQq765lWmKzb_f57SY7biVmDaQ8uRMsVLCJkp8ApTgJExY6njbGVteURG-nXg1072ExYmdif37aZwvaYpV-40uqYX-2E9xjuW6GWZmaDjIPj

    d)VtgFdpBO1CcfikJi39bPGidkxwd6f0TtwSsy5dK7wnaN_zESFoNbO57u0jiQY13_8So_7TnourpvVtQ1Uu_Y79EiNahmBCldebwu_piBBJia4paIRC1I4jEELolXi1PXhJzBifW5

    e)msfJI04yag7grXCaqNNE7Lgvo6vTtUuhGYfRbuwqIOBqTfg6KIQJWdSs6eb7DnbcWhyI-yZntRnpqWYtH1PK6uiGIbqcohtvwYbTeEBgQaJldwiVDUvqAFKUYHolV_Ajp_ZVEBtK

    7-19 Identify all the products of the following reactions and specify the major product.

    a)3XmYuZpxO8gU8lU_0-ji68K3-v_v5cURUT1UUa3jFtTAFSBu6deCqJWrpEdq6bQuUT54nc7fvk1-BU7zH6PdUDMydnXLKB0kv56z7J_1EZWrIJ45UyWyk_-SiXMAzl1NMiTqeabj

    b)KlfOvoOna7_5A6I6kuMNiGaJ-o2on_Z7bX5sF0rbrpfQyvhtP4FqUfPZ-YI62ASiRuLEyDPRsKRuST0CjJ0_IDhafBD-eyfld340-CmIXZPq48Tb9eTo9ArPSnkvarI4GFVC0ifq

    c)LOmc6XfFjGNgy9RrUcID6LMp53yNhKNn4mAMsosn-I4kEI8kRnYw-VipxXQYuxdCQmCW812hR5Yc2igS2MaoCFV0jqi9g5_D3tl1dVtLxWdg91MdzUx1eiKHUO5Lp2IbN_NKfHTe

    d)EOgI5PPDAmQt4ieBkeCPHA_kqbi4r-VGSSBEN5S1sGyHkO3FVXMHECnq-mPSourY-TvP3S0N8xb-CdfS5fq6cCtr_QrX-rXafHHFSQoEQPJW7n4HDBWDa1N9L08bDoKNt6zCKmdo

    e)IlDfpNvvs2pRog_QM50JocK2hhXkxaYMya93wS2qi8c1XaaUPvUaFymLBinAhCyZtNjrBqsBBYeAd8YEADkG_EKVBEA8X8oGp_z06sPzFDAlPDDHwQw2wb2zGvGu6z6D4ZCCKv4V

    7-20 The following reaction yields five different products. Give the mechanisms for how each is formed.

    Oxl3rKpIO3XdWjW3K2mbhi4TjHe0KOmpE3pB0lnL-l85GQB74nP5sB1MvOorDiuGhCIUVN1F2qX6a5e4DWjIA7xDE6l75Fcc0WgMijgDlOS5JhIWSSIaEPXok7P9-7HO2O1FF-Kn