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9.19: Additional Exercises

  • Page ID
    122586
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    Addition of Hydrogen Halides to Alkenes

    9-1 Give the IUPAC name for the product of the following reaction.

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    9-2 Draw the reaction mechanism of the previous problem (9-1).

    9-3 Identify the product of the following reactions.

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    9-4 Identify the products of the following reactions.

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    Addition of Water: Hydration of Alkenes

    9-5 Identify the product of the following reactions.

    qAnsODiBEvx4JtUioIiySVfY8lML1rljIOZ3CHf5qnXAG8TTBsEHzjSThJPIe3Of8YYUVkqCx93fC2LaeJ5UJmTvAeS6Ja2UnpvWv5FP9Bw9pO5XDk2xGnSyD1BQrUsOfDjd3YgB

    9-6 Identify the product of the following reaction.

    -IshetOP9gr58GHDUJGXmtcCY6J8OtchG78sov6PtLxWr4HnU4Nf46yndDsYnwOAYe-jca-K20H_cucTxelIXQL6PfMoC6BBlRHWuKIs0QkzgbX1-49KnBL3eEzz2jQQVpYf1UYh

    9-7 Propose a plausible route of synthesis for the following product starting with 1-butanol.

    qYGT7iuPeqYb3HxBKkxHqRjHYtLO351VnwginZu2fPI7LgSVi6VFUvp9Dix9Q0tKTaEw6saf9rt7kQWSPOa7rQeX5yFm1H3gwPcdaa4HvtvI0uHk0q5tcUjWlJ3ULylOlQy5Lq7i

    9-8 Which of the following alkenes can be used to obtain 3,4-dimethylpentan-2-ol through a hydration reaction using dilute acid?

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    a) (2Z)-3,4-dimethylpent-2-ene

    b) 3,4-dimethylpent-1-ene

    c) 2,3,4-trimethylpent-2-ene

    d) 2,4-dimethyl-3-methylidenepentane

    Hydration by Oxymercuration-Demercuration

    9-9 Explain why hydration of an alkene by Oxymercuration-Demercuration gives the Markovnikov product.

    9-10 Identify the products of the following reactions.

    SFuFgvQXN64VpkMHEV9Hur460TZ5OchSUmpCfFBd3nU4pqmVq2aIQcVfw8VeFfX0kYZez0kj4-qciXkYE_fzdlgP8aG3iS_oaESFrrbPwNa-dgzczUytst0AXbxE2yoauiaMxxOU

    9-11 Identify the product of the following reaction.

    2OzRiP-HBvBICX7flAydDOKrqWkxF1T4xd-6AxGw7wPiPXu5-19dH0jWwsz_iIc8znyO2mIs-4F1UROb9K1P9hH74Z4CzwKxXnbT91Bg7P83rE-8ffd1nmbSol05zTUNkGnoL9Iy

    9-12 Propose a possible route of synthesis for the following ether starting with 2-ethylbutan-1-ol.

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    9-13 Give the IUPAC name of the product of the following reaction.

    g4ntIHvlkSCxSj-JX3bju2zln-F3FOVLbOQt_8Kl3M4GlbSG892yl0BN-i-UDayEbrUOHocl0ICBXHDVzalSyJMFlfF09TzZYjPeY8XiAfUq2y-ILWkVoMwiuiDYJhVTTB2kV9kx

    a) 2-methylpropan-2-ol

    b) 2,2-dimethylbutane

    c) 2-methoxy-2-methylpropane

    d) 1,1-dimethylcyclopropane

    Hydroboration of Alkenes

    9-14 Identify the products of the following reactions.

    Ifwu61HY_y2PDtkDDsGuT93-2iCugg4QVosE0j1QRc0vBQz6rtmDppXR3VmlKv7hFVALCjvahq8Sq0Y75BMIBxhlPxEXHagJPKbsi762xBGJjDcskzNV3bUEGtQH6YQs3P5BO4BF

    9-15 Identify the products of the following reactions.

    uOJtWW3YRWrBYNqM2g9JzvGVIAVicuJnmAYCmaUYviwyVntgXIN4-djFQrz9XRV-Pj_b9s4frIUQmAXok5IJ-NZGEdrbydzsLfoVSHeblWOIv3mmnLQWkk4pbgDrKeu9qrH3arI5

    9-16 Give the IUPAC name for the product of the following reaction.

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    Addition of Halogens to Alkenes

    9-17 Identify the products of the following reactions.

    2tWD8ZgPLeaXcmn81R4SsmSeBG1sDt6X1XqVFQmzREzbqytNmfOnj213sAGGvYN9B4VNA4uRsclzK3-pI3U15YJlovIvF4_HIO2gSRMxuynM3Co1EdmYYv1HPCTbeH_MiYURRvEW

    9-18 Identify the product of the following reaction.

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    9-19 What is the product of the following reaction?

    dE5mzgTq6ydTm_4uYbe15x1nl4Rbc2uphmnQjIMT8qP0DmlDHdInZNZ0F6-cZiq9t8fZmH69DmTpZCpuOLZNf1fW9ubuHo5V1HplXLW3dhdyMCQ6ESrR_-qORLEK65EOpO6tXt0X

    a) (2Z)-2-bromo-3-methylpent-2-ene

    b) 2-bromo-3-methylpentane

    c) 2,3-dibromo-3-methylpentane

    d) (2E)-4-bromo-3-methylpent-2-ene

    9-20 What reagents can be used in each step to obtain the following products?

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    9-21 Explain why you do not obtain a mixture of cis- and trans-brominated products when you react Br2/CCl4 with cyclopentene.

    Formation of Halohydrins

    9-22 Identify the product of the following reaction, making sure to include stereochemistry.

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    9-23 Draw the mechanism of the reaction in the previous problem (9-22).

    9-24 Give the IUPAC name for the product of the following reaction.

    kHM4TUxseRw0wYqiRaEwwYckHZaGfBVG2TgOBGVATm-kjOlrFkUNuFxqlO_xY5XvZuijsEis7XY1MWNF5r1ja2RQx8upfOB4MKuzh2u1kUpnjYoRvyBr3UXbfgFmI0zeKv1PkHgJ

    9-25 Identify the product of the following reaction.

    HpQNOUrxU4_zdq6MPVhHRsE9npoSdxzKcT_siuFQxfZVMdNz3E1PTTFva-032OsorGT2h-khQnAU7fKsp5t6xCxAuwZPNuxvowgIFwGVrDbSgASAwS7Dvn8FgL-4GNbONc2bq5gi

    Catalytic Hydrogenation of Alkenes

    9-26 Identify the products of the following reactions.

    c8kUbTCIuV7Q4z8bTfQh5qpr4GFEnmQ9LnyiQXo_ks_xwnVVxlDiTEzGuqU0t4-FRoZDWIvRkZJgCqacdaUtYEj2FOrKzZINxO13cm6hcr8Lhiq9E4g9Rq8Z0k6Qyejta6lX9y_X

    9-27 Suggest a possible route of synthesis, that includes a catalytic hydrogenation step, to obtain the following product.

    uR_XlIB1DYZrXtvby5OPEV-b_Hqj_lghaZjjakMtl4ZvbzUugzD3XWnNqCdrJYTE57EQx-lVOh5gml6zJV7eA9CQsLsdJsKv_7eRZUbh0TG7dXY-iI2smY-9OlFC35vYOI0xaSdj

    9-28 Identify the product of the following reaction.

    9xoC0NP7H9IG1fbqzF4bbEhCuQ9_K0IEnMreqV-I9Icy657qvPUrLjZ_OszCYWzy6MPebgqXu7eW0A4Z8VlunW__sabFRln-4KBY31PrmOttsNy23SsN4XFSvdt9Xx_4X_YRHGBn

    9-29 Identify the product of the following reaction, making sure to include stereochemistry.

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    Addition of Carbenes to Alkenes

    9-30 Identify the product of the following reaction.

    vDmOIs29sDEwMWQkOvlJHSrus_Wgn9GurteSUuOXQXL1KdDfplmQ1nijKqURjBBF3X5OhB5Zxj9ahVL1caeyCrGwab1kN8LGVlbkL_5vSkQd4F0AjjS7f2vcHoiCdsSUw0eGi-He

    9-31 Identify the product(s) of the following reaction.

    CEi5rCbDoOF98smVZdaBZiP-Kzc0mXg5FSxWQZFlALz7zayWKRHREk29ncGc8_uKVbRBWIJJ7bTwivMPp_Q0PZwn6PBL25Td9ZeRGtZigbrEpjwZnG4sGkGUlGBP4W9AxBhvjbcG

    9-32 Identify the product of the reaction when (2E)-3-methylhex-2-ene reacts with the carbene product from the previous problem (9-31), then reacts with Br2 and hv.

    MTgo5MSl6fk5wY12rA2yjOCnDdWhvGIhxgDGMTwSXEsKQpE9jbPo3o4zr3HRrBQ3ppR_Ori7jRBw4NTI5xGfQdftjF8geQDCMey4DDSq43_5o5uFjh-gzHEsNTF5mYXT5ygB3WTV

    9-33 Propose a possible route of synthesis for the following reaction.

    _jncr70D7kgx1qYTzpUXOAixP9WpaldXDpV9yHu-knRwEHA6OydEoawT1xZVB6XUoCAkcIOpxAdSSGeN_g9O9KkJLo8tlT1ljl16JGVsBZkflWqEnRT9aJSMQYNC4brW7UtRmIUl

    9-34 Identify the product of the following reaction.

    k-F-hEAbKnxEysc7PsE035adq5fXlXu_kFCdg48QQYszwj_u7xgpU7G2_wXyEYaxGBTPqwloawruj6j2sTun7Ai2iedmT6Jz6BcCdmQfRsRhpJEwCSf-usarCqHeCMx7YpM0pD3D

    Epoxidation of Alkenes and Acid-Catalyzed Opening of Epoxides

    9-35 Identify the product of the following reaction.

    21_8ED9-CK8cDADNBGTTThoAAcHbiRQxsV4hEZNoNzFHxwDvCr7_64SQEfg1kbrJLSkkVPwiYvYP8C_T27L-7qe4Ctx3tAguuc_e8HCvEsg9C2maBQQmIFqpd1fV3HPwpmhxcB8m

    9-36 Identify the product of the following reactions, specifying stereochemistry where appropriate.

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    9-37 Identify the products of the following reaction, including stereochemistry.

    NjxjTQ5Z7xJrbAYT-k4Zzyw_XcLFSnZXxZnVafCBEUyktcA541pcOUYZWE2OYrcq2jtqWIIQVM306TFruptGAIpDgZal-qPWdt9pk72u9oz8uhSpzu0KiNW8jnhXnBM04cU0fgcW

    9-38 What is the product of the following reaction?

    sNVkf6mRg3Q9i5O4wr--J4zDF6LYAXV2bdb4G_FcKu3iU5dnKsWomJpb9V-2pBjayqbzd9RkzzNBDJjVmxjJ3G3J1hh-HkLYdFh49Tj5ycnnN7G3iYTtk19lNP0w3FzMlMy05lFj

    a) benzoic acid

    b) 1-cyclohexylethan-1-ol

    c) 1-cyclohexylethan-1-one

    d) cyclohexanol

    9-39 What is the product of the following reaction?

    kFREDn-sq9Xeg_8JlMkKiFFq7ulQE0D5iQa_iaNOXVCxV_224Wra_TjKQTOSrt1s2xMKlK7YFiJM7-h3i8GJ0hbJMyQ1-FoA0by3Pp6zWD541Gr_XgPqziDYKkGGu0fM1EwBD-tI

    a) 4-chlorobutane-1,3-diol

    b) 3-chlorobutan-1-ol

    c) 2-chlorobutane-1,4-diol

    d) 2,4-dichlorobutan-1-ol

    9-40 Draw the arrows for the following epoxidation reaction to show the movement of electrons.

    5hruGib9gmZJxMhgZZ4UCpFrHTclPNpL65XHR8CPajCzO-6v81he_Lb_QRghdMZf-Zx2V7QfpHjkuHBvSBd5PF_capN8cgrUAmFOlP-7Bt1hvMnVPmYctkXoY9grJfgnfuVhBKAq

    Syn Dihydroxylation of Alkenes

    9-41 Identify the product of the following reaction, including stereochemistry.

    F8d-i4-yPf2IVuPrRuDXfsM8mD-W2r9qV4zJawjMoFB7a0_1-cr58LI2LWU4TBbA1G9_mluX95ISLDhZs35i6kaaGq3J-SJ7SFe3xeN5Z2VZjJPtu_oVlFEtNvzQgzRxwuQ8_v5T

    9-42 Give the IUPAC name for the product(s) of the following reaction. Include stereochemistry.

    tLUXRXxbKYtsv9sKWY0DJAoBkk0URwcxetxzYZu4pkAq0AGhtPTr79V_-ZQo20KW_xunR35TTsdWyLPJlNVNAt6FdVqzSsWmcHc4W6xbW17SvJc6j1p3xa9PeukP28ovXkngasDF

    9-43 Identify the product of the following reaction.

    8oTt-sTSBpCT7tfrCqukYk8s2S3ND5kMlyYGqhLXkbnKYoyX5TXIg9TfUNHH_-rnL7naPfAdfqk0kawpbcrdLAU5J-2gFRe22lRm0iep6jOyBKz_l0RQ5Uy82voRSxGB8DYAhRKQ

    9-44 Suggest a possible route of synthesis for the following compound starting with cyclopentanol.

    UkS6WGPniOH4dBCDAf2NQC3fEYNv0aW6NbREW870uYV4UwvYxpuW8ipyoFT6hKLXD6j0S7MxZ9tFQkRViWb1iQ0ndvv3eIb0ZIErne3zBxNhVZwPt1seyhiQrwIO6RaPgSbDlM59

    Oxidative Cleavage of Alkenes

    9-45 Identify the products of the following reactions.

    Bt2hp-IaXkXbr7rk_8PdJ1AejVhzUhEW0CCxFRJvYvpOZJ_tFOHcEwJygCwdxPTLUjKtXLL-T62AvCOMrPReDiLrz5Ex4ojfEuqFjZ5C12sZLDqJyPPwI1z1QAyRobz0whwWBCMt

    9-46 Identify the products of the following reactions.

    N4CWj4Ld3KF4wYZukBnsurAZVHV9ERsbQ4Xo112vgK6oHPRAVbPk0-Hd9g2_GWYkJxuVjzqjXG3-wK5oMS9jzM1OASVluz2ULi-ypJRH2V46CD1UhqksaFy3ar46RXG64Y1vKrJw

    9-47 Identify the product of the following reaction.

    jI520E7a0lHyxlK_E6RzrWB8DyZEpJhTjVTAT_EcRJSaOuorxpteLVJpv3G288Z8Njdx8cqnwq10WBU2eyerNLmNxrWpX5U5trCMRU0uPlQldkB1rsE8YBekx88WwQeJu1FBUzUc

    Polymerization of Alkenes

    9-48 Identify the alkene monomer that composes the following polymer.

    CrkqN28Vl1hvDLp-xN9eavfrvuvPQjO415RBy8r1WQSIH2nDwfvHhBTjYQQie9vAL8Bht1S2QY1gkhXiOWFbxpuAoqGt-9tb6e95Iyhesh8awHGwjKw87e29vOv-yy9_LSHkN1qF

    9-49 Draw the mechanism for the acid catalyzed formation of the polymer in the previous problem (9-48).

    9-50 Draw the resulting polymer of the following reaction. Draw the chain four monomers in length.

    P4O-g-q5ebV0kcX0osmhCFU_DNjM4zEHTnjESxSx07cnZgE4pTyqV1E3piD-PEcLhKxJzYzmGZLjHca_3QFe2ISwFPX5DGFzFH6jQ87Zj_eo_BAN0iOkgLFkCluz0ORB3l_p3lNq


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