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17.13: Additional Exercises

  • Page ID
    183087
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    18-1 Draw the resonance structures for benzaldehyde to show the electron-withdrawing group.

    18-2 Draw the resonance structures for methoxybenzene to show the electron-donating group.

    18-3 How would make the following compounds from benzene?

    A) m-bromonitrobenzene

    B) m-bromoethylbenzene

    18-4 There is something wrong with the following reaction, what is it?

    18-5 Choose the correct answer.

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    a) 1-methyl-3-(2-methylprop-1-en-1-yl)benzene

    b) 2-chloro-4-methyl-1-(2-methylprop-1-en-1-yl)benzene

    c) 1-chloro-3-(2-methylprop-1-en-1-yl)benzene

    d) 1-(1-chloroethenyl)-3-methylbenzene

    18-6 Predict the final product of the following reaction chain.

    23b6TlYLBoV-aX4LkLl6m89c0hWvOa5_NPb-Kvlc3p4evTxCRsfXx0s8PEvMWMHt3i_RbBNIjZ3TNHYEYJJdMRpdP9_-vEWSnAQgfpJkfrhHrIK4uzWCdsC6WUSOboKozAH30LoP

    18-7 Provide the final product for the following reactions.

    zduMgVeVSSnogs24WjwCjOAFmdp9aB02lTQS6wz15iWcWMKGPKNC9ZqVnhU9uFMp_xnQ1q8ZPSoz_ZVQm_kizh2UDQ_NR8duGYuA3YVe5SnM7b2FmBYHPnNhXhEE_mVbpyTpJmrJ

    18-8 For the following reaction chain, provide the intermediate and final product(s).

    gFrsSY5o8c_ei0PXOF2wmd51iRzYn61JqUfLTrMcdLKtjOyww46gGQ9IAanBSQQsEh1jzoifRRt07BT43NfIJGKeLLx2PllT6V13K5gfyu4A4l-axl4Lxa55WGq3PnnFVNGlkyv0

    18-9 Give the IUPAC name for the final product(s) of the previous problem, 18-8.

    18-10 For the following reaction chain, provide the intermediate and final product(s).

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    18-11 Give the final product of the following reactions.

    1dk4UfYOXJ7lR2_j2oheKaGr8p3ewesvfQlGNWvNIHG1BVMnE9VZ0NNa4e7cRSZFFx4rQmGMpcUg6YAsVKdncvWahpsy5fMNdaN3SdXMyUjd7C4ZbhYXQvGpcJcLNs1zTqQLFthW

    Halogenation, Nitration, and Sulfonation of Benzene

    18-12 Predict the products of the following reactions.

    LMaiGGW9OBkDK5_Gz86TZvX2pq5e13ItJ_XC1icWWOWd0BIWxTvqoM4lFmpzmij9WOZcQZ-jLsJez0tUN0cWG_R935SfpKwHJZ3yj52UwjVgsdo_xj52fs0AmUuZere3kfwn-fJ4

    18-13 Give the IUPAC nomenclature and structure of the product of the following reaction.

    9hsx1W1PpjdoUuILkSV1Ng3c_86SHw8kKxy9hIHrPIelv5ObvTntDytMVig4jroGL9Go3KzekscjNyHROb94tkYSfsLaBM73hIQb0efT6L_Z1ZJWErf6xC-vm2A3ZMq1xsGwh2wp

    18-14 Choose the correct answer that describes the best route of synthesis of the following molecule.

    C5eVjbaGbIjcccjk7FykYLdYIziHu1Lb8Mvt8EcPBsVhRMDDe64d1ZOUFz0SpC0MRdvgsxylr1mA-bM0B4luR9tEt3cTy04iXujolZsEbE0fRJg5tF4cdP7n_r9Ixpx8DUar57ja

    a) Chlorination, sulfonation, nitration

    b) Sulfonation, nitration, chlorination

    c) Nitration, sulfonation, chlorination

    Activating, Ortho-, Para-Directing Substituents

    18-15 For the following compounds, point to the position(s) on the ring that are most likely to have a substituent added.

    NM-7ZeHWfXMthU4kLkTwJojXyxlhCBn9JM4tjvUBV5U_S_uGPl8abh9TC444zRbydU28vsQpDYnaFLv5ESFZWWViJL5-BqMiIljRQs4HEFB--9XX3rdMialEjGOw9CTmfmT5EUA_

    18-16 Predict the major product of the following reactions.

    5RdBZLKytUxnDnXn9RFPzEGTPZijkePa8g219met3zsApRRnTdnZOj4wHKt9ggF50_K6vR8zMrRvX00nhj8pxp4Q5absFBzG8VGF08s5ITSjRB1nvQbTp3V0r8S0cFbvBZYsi9c_

    18-17 Provide the correct IUPAC nomenclature and structure of the product of the following reaction.

    hgfKBswLk7rm1KnCPnI_B7LM3ci-RKmtKxOSJYNJ0aS9f32Vv1MdCfasuUhLC8JEGN25z7ctm7VUQuMyTAVzhd_vBlSAUojkVIJPJSoDFpdM3Dh8s1xnBtT0FnmB895dlJT_Lh5C

    Deactivating, Meta-Directing Substituents

    18-18 Predict the products of the following reactions.

    5M9eEsifKUzy8-Nmp_rnM8JENGJ4h_83jPnDPsozq0igD6LTEtsxHfup1UZevL2MC-E0wzevNNBrPXzRBcnSIinL67DScCPuQZYhZYa6EWZ97vhxbS0p0HhEgVUoNelLcAs6YJ_g

    18-19 Predict the product of the following reaction.

    aCohAG17lYy1c3KT_5XiHVmigFLMx6PN647oSe__lFRLwbfYMATb7gYdTGKK8roIFwtY_cNkXx0N0b1zLy8XKWoWRpMLdn5pFSgHZRRCbmuB0CdDbNC7C8JrhNDZLrjZf3UCgtRi

    18-20 Choose the pathway that will lead to the product formed on the right.

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    Halogen Substitutes: Deactivating, but Ortho, Para-Directing

    18-21 Choose the correct IUPAC nomenclature of one of the products of the following reaction.

    glrxpulOkmYksSxhB7IIMc-hHla_hfzwH1s51HnUEFZFA5DcXbZbIPr2EzNybQoQfoOg1VALpK0DkA0IhW8BeOlJvDLWZs13xUMbQtZPZXPjv6iCptMJ4oWzNoYuG_YF5C4tr0UK

    a) 3-bromobenzene-1-sulfonic acid

    b) 4-bromobenzene-1-sulfonic acid

    c) 5-bromobenzene-1,3-disulfonic acid

    d) 4-bromophenyl hydrogen sulfate

    18-22 Predict the products of the following reactions.

    8eV-RXx2Ff32ZwE7G2zKgCApAd6VMF4qzX-HeaAufQKB_W23OHHJYWK_l3aLLsmqa0_BGurQSZ_QQHaviJReIB9ZOXjrVZdm_u467aRvkZAUOLNLrMBJoYCRMiRMscHM_GxCrfOJ

    18-23 Propose a route of synthesis for the following compound, starting with chlorobenzene (assume any desired intermediate compounds can be isolated for use in subsequent steps).

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    Effects of Multiple Substituents on Electrophilic Aromatic Substitution

    18-24 For the following compounds, identify which substituent is the stronger activating group and predict the position(s) of a subsequent electrophilic aromatic substitution.

    OlaB11CBBLMa_Pv3KxKjbFrSHf2Edz8oRg_ZVYU4Lv7aAFXJqEyDjAKG34vyYLWzFMWAVVlOT1Y_TRc8Ztp_HooxTYD600E9fKFIeO9o0q3k6yi-zC_r-0ANMk__SkOSgszpZqPN

    18-25 Predict all possible singly chlorinated products of the following reaction.

    ZXDhPrY5O1NA2QZXOgKxlAoyHsc_9iTDCoxQP6u3_TFyRnB4WJ2gVhiFDMB2-i3UIrYCxDjEGUKZz2HlVTH933vMxtTA6cgpKIfzNztClM3dCYNp6ogoYvtbnJxL4s7X097Nwnnm

    18-26 Rank the following compounds in order from slowest to fastest to go through an electrophilic aromatic substituent reaction.

    BapalKkTKYhzp9kTKLPSZzy9Wc7RBNhdx1f9zx5B4sLpuQEGT1BmdBqZAaJucDc8O6V193XsTI9GBKLtg2iHHLm6zTDD11EpaI-oMl66f53IHXCZ2h0xXJFMM82AVnvNiPnAH-Cz

    Friedel-Crafts Alkylation/Acylation

    18-27 Predict the products of the following reactions.

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    18-28 Explain whether or not the following reaction is the best way to synthesize propylbenzene and if not, propose a better route of synthesis.

    5jGUkhnfl0DmGa4xZ4cpbEKhGdRh5WB0URCw6CyF_gHmdzHZugKQfQ6b5kxt1WmfjD7Zmlg4cSRW23wUqC4iE2RT1QoIAWvQ83Jk4fIMUR2oigKpKaS3LV0PAdpVyL77T3VRjjdD

    18-29 Choose the correct answer and if a product is formed, provide the structure of the product.

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    a) No reaction

    b) 4-amino-2-methylbenzonitrile

    c) 4-amino-2-ethylbenzonitrile

    d) N-(4-cyano-2-ethylphenyl)acetamide

    Nucleophilic Aromatic Substitution

    18-30 Predict the product of the following reaction and provide the correct IUPAC nomenclature.

    fSjz3y7ICGMHEakYN1bXj4poTQzKPNn9a6-5KLeuYSxiTl6GftQHcNSyBDht6vgDraSFcALM6vXLdnwf5QsPYQV-Kxp5-LgYQs5B7L81oQuB_6SkTSH0CnMkvzbDvb_f7czs8dxf

    18-31 Predict the product of the following reaction.

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    18-32 Suggest a route of synthesis to make N-hydroxy-3,5-dimethylaniline from 1-bromo-4-nitrobenzene.

    gKNn1hS-a0KeUx73o-WFLif1JxLwFu3KPsH8HckILM-PpU8WpFEQfjxJm72nAXLy_IQT9AtUIF2R6kb8NHqUSqZceV_CwmwheMOoKd7svzS5HjxBaN96VxlK_FdAg7KHlkD0axPF

    Aromatic Substitutions Using Organometallic Reagents

    18-33 Provide the structure and IUPAC nomenclature of the product of the following reaction.

    Rm3IwECCrX7agay9a6rGal61bHoZU4zcfsN1s1T1i_uGSAhE2SO2jMMXlRkIDiJr1xgz232CKsLijC4l-lPF0Jo50SPwvbIc9iJ0RtrD8xgmuE4IIZHblzPz3o2zdALbJZLLoVBc

    18-34 Suggest a route of synthesis to make 2-bromo-4-chlorobenzoic acid from 4-nitrobenzoic acid.

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    18-35 Choose the correct IUPAC nomenclature for the product of the following reaction.

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    a) 2-bromo-5-nitrobenzoic acid

    b) 2-bromo-5-cyanobenzoic acid

    c) 3-cyano-5-nitrobenzoyl bromide

    d) 3-bromo-5-cyanobenzoic acid

    Side-Chain Reactions of Benzene Derivatives

    18-36 Predict the products of the following reactions.

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    18-37 Choose the correct structure of the product of the following reaction.

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    18-38 Provide the intermediate and final products of the following reactions.

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