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Chemistry LibreTexts

6.23: Solutions to Additional Exercises

  • Page ID
    182922
  • SN2

    7-1

    a) Jharue7oaY9NKj2PFbGzw6s974ClW78soMx_Lt3fZ0rRMfT-X7hol6DQIWYk3nnyejKqt2qMNpkViIDO1gMP_DbyNMVD2IBWup1AGPYy4mJKVa-I7VcRMBUosRltv6XOqXp4_rbM

    b) 02gZZTvOXLlPUVjELuVUIsbfZYRsR5YEU8fvC30HhrqCXdrT6IOT-bNpinF-7INmXG3xeV4Ad7elzdIG1Ls5mFvNM3b4gAxh_8cDpQaEzhO2zMpwiJtU_bFKPR7PL8nrpDHF5YPh

    c) 4dAw1MdPyzIIMGDSE4j_MMIaWz0oj6cX9BamCq2rWoxxJ03Btt7_xeTgha5ur_BjU2yHQPsFvBppDEgGK9nWqQp8jD09Apn9b8nGaUICzWNugduRqK4AxBTJHtrjKR7lan49heVH

    d) 6WbDXEmNnGN4Uy_gBiZ5Jgk00SaaJirw-gwT3_TZldB4xnZc9M-1OJuavtv69t7aZMh5FyQ7jUbtPgrtv3EiGcBpt0ViAOh_aTeXufdMX87xoRgen28V2BkFiF8Jg6e9zrwPj6DG

    7-2

    a) kB355BcBgFGSL6-OecHGL6Dv_mbS7s-6lTm8G3niVdKJ6PrxwMLCdD1krWdiH9EVCzSmxbVw2RBuvIvbilU4RCo-B-nyby7cDzlBFMcf1NantKB0Jycg1oxPkVXyq-WkcoOqFFBs

    b) Xx8YIhpWG0uuvJCdGZKG87Z10JkouIdaczVLu3U6lpz63062WXN9B8gmf5Ht75gNNMYdxhQ1zHxXp6kPQl7Dfr4LrlF_qadDjRfb6kczVgAzZaX2kjs0lSLdS0SkKmY5dvY6LJpX

    c) No reaction

    d) IITRvW7DmoU5knEVNiS4kI2J8du_rHVZLFnBtZH_xX9KLNuz9Nz2tSCyeQ3F9EWEKi5lyFHr6Bv0LK0UBfNFI5GKUcmYQZHAwRDheF2e7d8TakVY809Ax-8EMznoRJD9GzDIcNji

    7-3

    a) 3p_lhxnFF-NKCmcJ0YNzTH9OUHA1AzQAEt3_kBuHvA377Ih8jO4fJNzMM_IvHD2xWbwiPo7Z60yKjaRHRuBa85mYNqOvka3qh6CYWx8jFFWcok-6zvAt47w1xx5tp_HHDhTlmw8A

    b) AxPFmILac_Qhr6RpiibgSkjvdL9qi-pOJjFGTWuHDCNl_RHu9sFhv2QfAVfYqUKxVl_am_Ob07bnUdD15DsbwGEtt72fF2iMG9_b8TsTXU9kvCVGtXynqNBNwm45eLDrePPYLFFf

    c) OlvhhBIRI-y2TkQ8GbGwnKthl0Df_JLFT1fSeSyVgm-WG7rBd3e_RwMmS2yDyKLkiMkHtSBxEQc9lDqjg6UwU4Kt0fuBMAJxvWgkEIi6sb-BtHHJcvqp_DNt6SzjPuIxx2GtQFpA

    7-4

    First method: dTp79-yZ-O7vo8pvBF-GKiN1NgPTKQ6zkCsVtUIaJXC86QuzgUO_07i03KhwTAAn3vvz9XVigb9ilfdbmjf3nxCwuWrCx-hUgWlRGg3DuRXSGX4hv7ArABNnPaweIx2SCVhGhbk5

    Second method: Fj41GpTgewejLaS8Ctsiy-D4uSl84UGn6fIV6H_IjSxQSo-kZTlPA3n-Eu88bzBwrOF-OnKbfKZE0FbDhfBExPIozHnERm8pmJj0moN_hD7dO1NK1xaXg7TJ1XjZIY6dFdBLF0vj

    7-5 The second method is more efficient since the alkyl halide is not sterically hindered

    8frXeStjxkVI4u_8C3JRLhC-c5xcwwDMkl2PWTwlRLIoybJrv9sBZN60fA195knBjKYjGFBZx7sIb_wrJug2zNr23pWWtRyJRb_8418CF0VAQxJvehMKuxtm9q_Jnz0ZBum8e9nN

    7-6 H2O < NH2- < CH3CH2O-< CH3O-

    SN1

    7-7

    8dyBFSrtjPNItaVZT8WFpvrp0qYJlCOyLSf5zHWfFVzOYtseYeN6L0hHWcnFmrqCuI4RduiFKKU-_PXCRe7L_mi57cY0Kodsx21z_RYWq27PT0BcK1RNOpsA10ZCrXWcV935bc1E

    7-8

    a) -0IwH-TR1Q0JyV6i6cRnWMb3ab6SclPPV9nnV4x3ikmabG4XxNQVp5b9cHQDy2tYIdrU3HMppMRdYctR2nsKEKxKpqYeQFTTbVGGgf1gb7TYrSuR644C4VbMKinPKToszUb8sPcm

    b) 8zJfwogFr-lmLCeAdFNlpvsDGLm4BsCsc7pwr3-KCLR3WBa5nfyYikTosEhxLVPDZUjDrLZf_0L9QPAVjPzhZ_Hu9r3tFye3kiOWTwhdtQJiGS1qzeOvkB77zwzqF9RlMs0iHGOk

    c) No reaction

    d) s3sBF19OyZQ91s8lwJapMjT86Mm7O86EgaLoQrAaKwd7RLUtEz17QiOUk6ghRciw0h5dCeH2LM37zXQTKDCt_Pfaup32FED0PS0P8AM34VMTujRsD-Cw4SH7Czk0KDI2vBqJd-Aj

    7-9

    a) 9-CaKwo7_abD9dpPOVk-NpaLhyW-UFA1hIitpNQzYdwPbtPaX0vZzY2ODzYCz_jnrMqPOo4mlQvk7b4ooot5M58_tKZcIt4ecBouJrh2smn-n4FO4L9-id7FZjFPEYbgwA4LvFn6

    b) -C3ECWWZjeM7cFxzoPJZjCYMxbWDALXal91zLl6da9KVAMxNLVYzdqX0VuujJCeQsZR9p5XLnVud74onCDy36bf8VnXc4CILANKpK3OP05hu8J8ZHAR1yifA1fHbLZ4Se0gmjCfv

    c) iX5vCpJNVm3VtZ14X3uDFCVHZGB8Od6hUiaTFMYHKjlYNXEqf-2_Akfn4XGkfZMQ9toI5MvAyXzgdRQutLoMd7yIw5plm8yd9MqdnhjxW-4cqnTjaIiQV-qO4SYhT-tdeDd8SE1f

    d) eKjUOvFYKzAHHY-5Vc8h1KcutWSwm9tKzCs8ttqC0CV1a-9sbQIqd-pL3idPc-6rVpqYENyrtm7-OnhsVNWsKdaHqm6Pq2pA5iVAOFAfPkuV9E2rA1ksURD227K9vQZKgFqWFvY7

    7-10

    a) Es112deQiKX3z_0WOC7kHRaUdXr2vc8c18Ut0Zuv0r3pI2NpQl65aR8EtNT9A4SPfY9z79-n2Fni-Jl5l8yT74xc6aapKa6CWMeClgZS16epovLL2d4V9R8MXvJl68zH-U-UjmdA

    b) x8W7id98y6Xu_eoRwaDa9qh1Xosoi7JBvoGgqSfAqo4T7aOSgZTInK-9xA6FMerd_Z4cndaCt1Egprb3OEdJJGhN_JcpuWsauTzcPbGQNutFdF7PFAHQnKrllIJpsUI2tS0RYMFR

    c) DxjiBc6XeJlBxQgo5XFm5F1vw8sqWKR0GuXXNXepOj73fr5D1oGrWX20tdJM9_GiCDDId3NZMn0V1Jpx1Ybud7ZcR_2Ya7ja_hjkxesOxT0tnGvxBDUTtcgcIuLHqQyGvJdUthaG

    d) YTvmOda4qCGpsiwCSvK4XSRkrUPX5ema6Mg-liv7nzUwbCGjV-Xi33EOWdQVeN3r7dG2rVS6AMicJZKu0PEZBQ90IPHNu2adoVfptKi9xoYK7S10L_vKHMqLyWgjE9sX-JyUOfW7

    SN2 vs SN1

    7-11

    a) SN2

    b) SN2

    c) SN1

    d) SN1

    7-12

    a) AuEKKRosVWXQtjSx0k6YVRD676jkZoVycYJW_YtMaJjHwb3rWDXoakOU8DzcQBR5YhL1q1fbwR0rVguvC0PCadLRl7BpCIhg8U7VofYstVCO16Y8Hm44MoMHSrVxAIpEt5olCWt-

    b) UklrjP0BTUwsjhh9OrEjyX9yLtyF1TpT-yVcS1KMzeEgj66YTy4RnajRbctjMJARMW2U-2svawPmjb0VXdbvDJEKBZsFrUaP9oeJ70bneb3Xm_VBS3ZGqjMnFknBgbO2EfZCJk8f

    c) qrA8wnTFNmJVpvSmWzWEEI01mXo5rXsIbQsF5hw_o1yHrup-o-pV3ksdAcei9tReqafcnL6JTxhHx6gb8NzLR6fKOkMCafK9v16hb1LxAPVd1Bw0PJz4RmbwhEyovrKgi6CT9PAY

    d) QJHWuYmahOTeozK9FnBCUG0FvYsNcu-UUyFCWVUJWrc1dPefDK7l1GK59wyE5xuDJowWkjzNgFkzhyjS8ascmMG5rtSJ3doaYEf0YWcY1nxAosdp9q9XtUhEgUoxzA8oZektsh9F

    7-13

    a) uMTcMG_TKsdo0vjky_s3OHoiVFpKW4tzarkfLFsK6QJtqs8rtlpT3WBDmf74r-p0qt1VP_kE0BuOQuOO5wUGIwSIqrUYMxd0E0nY01koTQXkZ5GSp5Q3B8BUFfMPZvLEWYMTmmTq

    b) k3lgYLCjzxaKCUbvLPE9tW1ajW_X9VKrogUaXtYiADM3EVsUy1caGQwyQGOWWrr9ryhFbNxhzQ4Cv7F31m_ZYLmmM3vvaDwCE3tOy3mrBGaw34SwOKptt4cZRFGeMdI6YEX_saNu

    c) L9qmjTmE7-VOwBynKTwaft6-XLol4nHky4iw0qVMMQbDeIbN8AG4_k4gOVMUEt7636RVWn_nPSGkcZngt0tPU211VDw-V_12pQiZCe6McdcIkVkNW5F3bggxUOA5I1n_8koBbFQa

    d) 9BgeOdnoLmcfYmzYev5zTsjOl65f7OV3NAYs0UVu_2GTqURyvmXwQNV7-Vjfd48nKT8uSNzKgPe4s3zYN2wGHkQpYL8xRAkypZFVHxXBfbcnFihZhMx9JBkv9-HnQChdsodytw0-

    e) hNrJGdTND1VKPR8B1Zf4z42i3-Okb-F60W3xmRjp_wKd2q0VDKuOmS6WHFI7G5d2CI8HLfWP-j9SzedsTnnQjrpu4IWAE0G7CxmnXtFMTbvllCAN6AlerO9vIhuBoTQhxFdFe-87

    f) LNAQSUFoiymZ2C6l9BTUvJSshbGYn0QyyZ8WCcI4pZHYc7izeInm7plGVelyGKMRVSgVuYOutDxaFpysvG20NdrJ8vwowPuAJDEhHn6vflfFU6EdVFz_2TIYTofxqna4-EcahCFk

    g) Nakpp4m0D4G5sv9MDTZZnuDvzK2p23c0EjPzIt4NMDsQmwrKXPOnCjT9rqQfo8PHhivmhuowrxivRvnq7TnfBIkDAXXt6XI-nIJqOhc8YISMGqWQxiv5OF6fi8m1j7Rih3mPj7q-

    E2 vs E1

    7-14

    a) M3gZZpkRYzlrdeuC2p8GUMW__qHlNej67aLj9bi0sVIWxQGze4uRdqiVfA745RYu5LkzNw7z2y8Jr599z81gviFo9YpBL6xBk7np1b5cvp9caxSdHXef9aRNk5Zc3M418BN-0tDJ

    b) mhhdNWrIeEP6GseKir8RhyyL2xieLbh5k7YWR8K740lpvc-sPgeM-_RkAKxmr6WXjHRn5NavT_wPbmRB_PeyvFCgcSN8_lH-gARWREJvcel5RpuJNBkd8sVkrQ0AQ4qQLMSIa4Au

    c) O0mh0GpIxfptoIahLmSt8TpFQXQRt_z7rpG3nttG9efHDCuHK8qTAfjHKaH8vlCqIRT8wdrh6im-QRLxeuBGfD28o-Q6ZmJXsr2Z3O65K5pNW37_-bo-o2RR2KQ3brobI87BVFjZ

    7-15

    a)9-43ZIae_iPhhNozPaLKj4I96e-6wEdOQzb6JjDPyAFbD1M76Tzg2XUQrHGRiP6Xb9XhO3uP2_F2m8PWIE8bEICk5geF58gowfXkmDLUZALdGbrSxcDNN5He5dNT8MVNnktUYNUi

    b)8Xps7uDR89U0XmFKNCQMDSAvqWfOHZEqGpKg6iwHMPP34iKeiF3bOcKnnfyptb9WNeRyOVjL4cFwyg40WS7riI0yXNyypmdMOUl9o1X60TbeLp24BNPIfnjB0ixuyTT66-qSwZYM

    c)QF3Jw2hPh1B94bCGzrRv7JqGhA6uaii43-Gfk5DRaRf_Bedbcb4Cep0IeZ5RsDWTlzKqIY0jx-z2i42h384-k5V3Oe11dI3Cemhp3J2llinxZz4NmgSYY-1I40jtpwLEEi-Eb0W3

    7-16

    a)Qt3ZswLC8e4v3wVEaOBKzqOg2vjdsRAUg8WyT0cEk3Eod4m-sJLoU-YhDIm-VpH3XIs1EEPWiCx1qVGtfJAB1uJr7sU8MIMSURyt7TCF3tbS2MP_gdA9XuFYwNmM4vyIdgoYjPZZ

    b)WEy3GIvH03JdBk2-c6opt2BXWM6cxvvV7RR-2uAwcJBb-BiEInKnMBgCLFdbF33o_ZjaWaShEahrRCEVLg604gmd__XfnGOVy-uzt1el-t5lJ9G4SeUvrsDKpnKIP86CtDzlVQh-

    c)A0yiENDCr0zcnG7bvnAqW_COeMdQBpn8ZN4OMaTHSBmVEFzMOfTw6Aah3B_t-GS91PFvoEHsY1egPz1Goxtm8RCIQ6X2AJuRAWgnpj4XE58R0znQohDHJx2Epvs3JUXJRvsAHds1

    d)2xs2xvlh1waZB5vFqN187g1rDtvaov5HvhXgv2k1yoJJqZGvhpwRhGjx5ZrqWYBR_9qreYRt1GBjDvYp_DQhQppq46QOrqV42eWm7l_xXMN0ixvFxYK_GplxPW3LiaC3keCdEfMz

    Substitution vs Elimination

    7-17

    a) Cl- ; strong nucleophile

    b) NaH ; strong base

    c) t-BuO- ; strong base

    d) OH- ; strong nucleophile ; strong base

    e) H2O ; weak nucleophile ; weak base

    f) HS- ; strong nucleophile

    g) MeOH ; weak nucleophile ; weak base

    7-18

    a) E2, SN1

    b) SN2, E2

    c) SN2

    d) SN1, E1

    e) E2, SN1

    7-19

    a)It-ybsifOx9Cr4aL2DZs1q3szIBCBUwuddxPCcDu0sUYpsegcv3iOmC5KjAm7T-1kBSL9clsPSQa-RA-x9pt-H5_VuOuebpQ6RPQm4Gwlhh6NXgyGWeu2jX503E-NuvrLBIA9CQL

    b)2QKalqyamcJMJglDMQ5BLXgTcnfA4OEx540WBUqJCZKl2s3vi8Vhbw3xCYBfewisvCutqm-KuwYlptitSWUPkVEqD45X_QzfChfL6xXCgmxKPr6iGZ_IYFqjfhmtGdqgS28yenyu

    c)8goeD5NH4HG95180mnLWhm6B_mxtG6q6CW_CovgQS3wc9am2tHSop3DjXY0-OWhJvItBJLyb8UkSFBb7BJhmbQA8sueL66Qe5ApYhiodvJrIHwPex5ze-onx5CqhNPBxjJ2Irf_y

    d)BrJ5jZ_x0cTuSw3x7GkNoGdHORKqg1xvSe3iXIsiVpLU4iI-5fYQTGZe8qgtEJwaldHaIkQFUjVzcna4HB5Hhpayz-iloF4AEw_e6jDYElRkruyIoQvQW4W962eb-VZL0s-BJrY7

    e)o5knrxhmMXLBsdcDFiO_POQMrtvr2yRGBChZ2ZragERLGa9k7m6Z0JnSl__ozm1Q72GbDY-6jbs_T-2RHXU0IoCzhnFfXghkt1k0xcuvddn3NCRHnzL3yqb6xxrT87P1JDd1VWEY

    7-20

    Xq1P70tLG3FVA7bJCW1wZ7rTZZZzXen8ibb0u6jQuSCXKoyrE9-I80hzTmEy7F9Ccam6o47szLA7zs-IvoaDE5b0CqJvpMVGlG7jRZYWVfAoktI1NH3HxpKO14PAb9_jHxWXUgKR