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Chemistry LibreTexts

17.14: Solutions to Additional Exercises

  • Page ID
    183088
  • 18-1

    18-2

    18-3 This is just one possible way to synthesize it.

    18-4 The bromine should be in the meta position. Right now it is in the ortho position, from perhaps having the ethyl group present first and then the having it substituted there. BUT the ethyl group is last to form, and the aldehyde and nitro groups would both encourage a meta substitution.

    18-5 Answer: A

    18-6

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    18-7

    l9yNg4fozxiQpx67483rx0rdZTdtrQSHS7MBC0Hv9BTSrg5QVI3gXAOdpGunVJzFriCC6dlolFJxJpWuEVi_g-4EvMu8RWPYBBn3niukBeES1k08UgtK7YLKA7HI1HTD1Ubys6jT

    18-8

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    18-9 1-chloro-2-methylbenzene and 1-chloro-4-methylbenzene

    18-10

    lIH0LwVqdILHSpwPqt0ddBOgQdwkACguSVy0uewiwWQzee9EaD64Qf5t-Kd-e6GjdUhOZuCu67Xcw--2P7j6Ykf0tT6beqvnA7H5W08QjHJGcl_Kp4XnvU_QmzFFm9Jlr3KEdHv9

    18-11

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    Halogenation, Nitration, and Sulfonation of Benzene

    18-12:

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    18-13:

    EGyhvqj-DctPFzk868EVdJ7CWPAYPe2cl3ghj3CanV22cTqvpReRt5ubKlskOxpJvm0K9cjrP41baoxMBmIP9ZPu4HjieUhLiEmOlLOUtvCaSLZX588ioTJU1SYYzhRy3srcMNcY

    18-14:

    Answer: A

    Activating, Ortho-, Para-Directing Substituents

    18-15:

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    18-16:

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    18-17:

    d2BEWn7aX7yOWCU6_KrCOp7qXGBY1ofjbvviPpoy7mSpxPcaE8iWP2oqGkfhNfG-BuKc3ssbTAt4uhiKRtvdbOox3lgHXwEBadP5TKcEpPawh4URYh5NA1WqWYzgVrHWs93OIXRp

    Deactivating, Meta-Directing Substituents

    18-18:

    bL9m_lpnGAC3MDrC34ljVVePheMtV2YZ69P_OiDcJ3JsD326yW8oOCbt8i4xJQeefDGGW0e3h8JfeYJjpgjDnMLgjqHLsmM5_cFwaZaXK9JArQ4AqeWMhj7eRmQNYsMZqKNgXquI

    18-19:

    PE1n9rruV4MXVs3oWmr32KakE4M6UVusWccfdx2KSTn3B0prqLNNA9BO85TcTFHKaU2_GDzDT0kL59hOtCOxqfQLO7zjjA5aHg7mdhXHrePIHFkBfWSRMFBioBjrIdxve0o_dZVp

    18-20:

    Answer: B

    Halogen Substitutes: Deactivating, but Ortho, Para-Directing

    18-21:

    Answer: B

    18-22:

    O9xuHDsB9GJFxVjdxwNcP0bLE-xxioZ9UJF6fC4v-RVHRTmRfAO1wofA274LJb8uBIAElK1pevNbie13W_bB-q4_MTXFmXoY7l7_nxtnBdIUUmq8Zv9Q3ODdjzzGjn61k2Z172oF

    18-23:

    NyoCE--XsfCWqWcG_zrO9OSQBy8D6OgX6ITg3YKCmZXT3gjNNYoRbNsH2ZzvCcltBn-knBHlI3lLdh3HVlw63B3OsevmxworpSM8hVYNLsgdrtPTFG6UO9v41TzcLEgZvSFRI_Qd

    Effects of Multiple Substituents on Electrophilic Aromatic Substitution

    18-24:

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    18-25:

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    18-26:

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    Friedel-Crafts Alkylation/Acylation

    18-27:

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    18-28:

    Friedel-Crafts alkylation using 1-chloropropane is not the best way to synthesize propylbenzene. You will end up with (propan-2-yl)benzene as your main product due to a hydride shift occurring during an intermediate step. A better route of synthesis may be Friedel-Crafts acylation using propanoyl chloride to make 1-phenylpropan-1-one, followed by a Clemmensen reduction to obtain the final product.

    18-29:

    Answer: D

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    Nucleophilic Aromatic Substitution

    18-30:

    pMyz7WmVrky06gto53PNbpZsDKhGQ6gxuK3Lw6uOHlLrouAaCREArixpH_TuD4AeyTscsipq_vb2pTL1yoLv-XYHvM_witN3p0pLZ7LxfXJ4tRzWpGY1kU7rNFNTxwj0LaAgeV-2

    18-31:

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    18-32:

    Possible route of synthesis:

    A-C7sazK80qhVGvsdb_rA55Rib37EW4MJiBo8H7gBwqYj9cqaBp71m3nIdD5Cu-7KExNuMr_pKbahpAbo9K-jJoeDxDbmhQW4DXOBj2Kjni5iOefW5vuvU39w0m-qpn4LnI1VoV0

    Aromatic Substitutions Using Organometallic Reagents

    18-33:

    4AP34-xmsKjLJPKinPXQaV67ScrCs-dhYB7o8mo3LI5bJ1EJ74ARRUm3qmV1QYcPv54by-bBtspR7eMWLgK3gcD12eDKfTu_5wSlyRnHiQJA-uhOvzy1uApvKw4D0xjTPQBjzzpH

    18-34:

    Possible route of synthesis:

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    18-35:

    Answer: D

    Side-Chain Reactions of Benzene Derivatives

    18-36:

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    18-37:

    Answer: A

    18-38:

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