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Chemistry LibreTexts

3.16: Solutions to Additional Exercises

  • Page ID
    122579
  • Alkane Nomenclature

    3-1 The structure that corresponds with each name is drawn below.

    (a) sec-butylcyclohexane

    WU9mVHVs5tLyEGBmjmRBU9ifjuJvom4HC4yVPMO_LOFJz3cwJDG0DC5TG-myxk_AkS-rd0-ey-S-DIygWCZjGogdx-Yeu-uRsOSLuohnhrb6vIBNwSGmmqMzPtm6bTDohHP_729x7zl1RtB8-w

    (b) 2,2,7-trimethyloctane

    sGQ0rm8Ae5vRJFkzACfUvy3SEH50FtGN0pnus2YZr2npolaH3owuZvxFiT8oPhsCkAg8qo6MA8oJMLQ8g7uvyluOcHL73W5l2QGV7_Y_R233Q5pwwMJ_cXff65qzfW8JS0YL6qP1OP4JBNNnmQ

    (c) 3-ethyl-2,4,5-trimethylhexane

    mybxYxvDjyRIXqedimqFRhbynhiQtpi33X_LeIoZXgnw8V3pshuYf1rk-rPVDvaS9fVVDIiKKgSBRiJs4j7A-ULtbI09zsX_R0Dux7ad_9pV5dCJ0LZ_JNbkVHtikULCslo3KnGsBY46p3YiDA

    (d) 1-cyclopropylbutane

    -u3FU_n0vQF71kulmZK244CcmgeH1hDw6IpXMpmPMwHTfcKs7LTQSwyLCXzhSXnH3KOQeJJd3BD3X0s4LFj8er_9pnBwL0pfm96B7ArxNSFOgeIjlGSkz57g5UIl8RzxeHzYqg3rGaa40uSLxQ

    (e) 3-ethyl-2,5-dimethyl-4-propylheptane

    YKAG-tY-FuI5LwlG_Y_q51pFB_GIND_unPi98LZqyEnazNq85FbXqI4qgdBDUy5iuQtUij9pjIQUyuip_icUAT9Uc2ICz8g2MoXel8cF96oxV8Z7hgQudidjuiZHBZmPJ7CA4UucyadfsAC7iw

    (f) 1-tert-butyl-4-iodocyclohexane

    Lr3FcaguCShGJ12OUB6lY65zW677V54Xe3YyhQG41Cga6Q6KKi329mw9k6OnD6UOiFLC8Jc5KNhDrCZyV_FK0p8bZhevZEJWkc6U_PhROua2CefS2r1Af735G2OK9L5Eg21OE2rJUReuSWlctg

    (g) trans-1,4-diisopropylcyclohexane

    WkigiWIFW7o4oLMtVJ6oKwl5LEfd3tBuPt_NyZ12HbvdL0YjQzy09Oha6br2eBMMQBNqKzxGg4j1S8-cQZxCZGsL8Zy0qc08k0zbqix1nvTp7W_w2q24_8oKQhPPCKW-Ag03DIg1pom8w4TgqQ

    (h) 3-bromo-1-cyclopropyl-2-methylbutane

    SNwL5UajnSdmBgGyixY9nYJHf-6lMW0mG1kyAqK2WkEgYj1moQrro1MUDgJuClz6UjWGfK3rJnxPnE_Lou6mdKtNgFCCVf6pms_13PMcvOUNIY839XWQSds1yRMtrSRtwClmjl2dvIn6fT8jKw

    (i) Z-1,2-dichloro-1-methylcyclopentane

    Qtj2NWCIMF-NsTRqDKfZ8EyfBlSfZDfhE9iY_caPYLmqL7Xnh0-fWG9gXIs9zBcxe_oZjamrtJgyjLqR-GuIr0cSn7oxCGzbStKapSnA92SzMrqWbgV8frxQRlZ9kPM2JvVDWr8FWJqUgKJQFQ

    (j) 1-chloro-3-ethyl-3-methylhexane

    USEhmskQb_GCwOfrxhW_OOkc4U_udxc_cbnrZGOSXyj8kugPzJKv4nRegaXP6qySXUDhUZuak2DztEBPaql5W936tNiTU0m-WFYq0BwAbmuMrt5wrlTtkYZ8xmaKeo_yQoITiUgLVrPnxcn7cQ

    (k) Norbornane (Bicyclo[2.2.1]heptane)

    lnxyCj4svG-JFIK9i-N9SqfRx1wyoeaP4EpGf0aS8wPepH9binHfuqG9Yx9hRx6OePnaAz_xyQ4IeMWHZsGVUaXjj92WRwKZEt8FoI0hIKyPUofuF-5e2M1J0Z2_Nodn6kTmhmRbxpSGKV9xBg

    (l) 1-[2-(bromomethyl)cyclopropyl]-4-tert-butylcyclohexane

    fWYq23BCR74H2usyphT8fv8ayOfDt7jOdFmhqPWKnq4SVJnCA4E82DBVHXrH6ZvQOACQhXgxA502Z7yqh9rfJSZlb31MabPWNvcKBjj3ixIiLTy4Qy_jE37C06U589xAgi_aZ6KX9mlz7YGh5A

    3-2 Give the IUPAC names of the following alkanes.

    (a) 5-ethyl-2,6-dimethyloctane

    (b) 3,4,7-trimethyl-6-(1-methylethyl)nonane

    (c) 4-(1-methylpropyl)-2,3-dimethyloctane

    (d) 1,3-dimethyl-2-(1-methylethyl)cyclobutane

    (e) 1-tert-butyl-4-ethyl-2-methylcyclopentane

    (f) trans-1,3-diethylcyclohexane

    (g) cis-1,4-di(1-methylethyl)cyclononane

    (h) 3-methylhexane

    3-3 The following names are incorrect or incomplete, but they represent the real structures. Draw each structures and name it correctly.

    (a) PulAKynFi_dn_4pIUIKrOVmObYp7m_7grQVVEPAUSllq9MG0axHhKfBmZrbEqRSw7spEIYnqgzGB3mAh_Uknf704uTzTVCQGm0W5zTbDiYn_bgVDVm4nhfs9LrqXK_QUitaZfGmDqQUW6hNfnw

    (b)-1gt8XQ6Pcx5jX67L4-0ape0T3WUJHpgdGEyNSXgs1h2HY5Ou8RfzzmtCom2D7eIUdPS_Sat-JmY4_kLJ6PaE9UjDBQ85Mfb6xlJPCHCYGOTLT0vICMZfe_fa5pKA0MzZsciQe6gVqL5WxXHJw

    (c) rACzNrqQXwT7SDDf9A70qJ4WaIdFG7MuoywoJjxDgR2NTOZkzoxvrvnbSsKpsZG4_gnzUCMT8uAGbi3BUWPI13euTLnzNtWwQtR9LnRnZRXl_JIsU4bulz4w5y7LeF3sW9gfMfLRxPiFNFhNjQ

    (d) C9dVRcaRLS-3craoYNdljqqnPqE71UADLCTwp6NzFTSRPpC7_bjmnOhqZOCQScMym0HhduaCkBJz8rCoqf0hUmqIWJmnCLqlEpSFxj4ROmoJAr8IvB9141fkXDoPtRLXir-sGjlcxmxEYsgh2Q

    (e) fZfJgxiEfdnTh0MX71ae0dRpfdxhS7hfaJMV4LIBPK8EEriKeK-Xx-3M-lTwPDr884F5TtyRA7z6OxRpIrU7zJB1aJMjSXl-5W4WGE17DuiFl4tXm2ARRADk4rrQm8-z0JjJc7d_chwpFTsxWg

    (f) iKwURhzEKRck6owS7wI6ZrfBSW3a8Wscr-30bWR2CDOpD1b-S9Cr9tfCANwxXkha0yUm-nyr055ii_JSiLkJLgt6YRbodtkwdPvnazJrem4poQ2HZecCc3Z1IQjEHaMwTzO7GsxVEuqdlfmd-g

    Alkyl Halide Nomenclature

    3-4

    a) Nr7j5QqMruehILoFg70kVpl3vPMTVZzMUAa2UlTa9Oe4WbSK1y41Fm2zjmppRjlsrw6fsA4y5vVHfHb-IH-J8KAcwktKaFkYM2iv7jVivOCEmGKmgR3XXsEeU46kKe6IVXIvM5Ub

    b) g__xtLniCTqG4vQc81wdO_2LfVgqJnRVrXCjbhoaHBjj2WEB_SgOYXNa1Zp3-RPI_cA3IN6Obe0USsMLm_vIFKJS51Umbx-CcfGl6xRdCoZjZGDWjheSeB0emhTwmJ9bpoI37Nn2

    c) xKrDLq9oXYnoRNBK_De1u6pI-whPy6wT7O6RMAv96By68GB6v53ZrhSUaIGm4PeST8nsO3n5TyRETHlJidFrL5NaA0D16EDP-KPqIVY8W_Ms9qhK0uh66_z7OTEzYJXDLzxQ66Aw

    d) ii32uqqXQTzPKd4XBiIScsaGe4RQvPOBCqUDowJEKn9AjWpTVXCGJtj3dnwAAgpZ4RsyMvPYiqjato-5E3qtcrDOXHc89ST3aeKMHS60xt7s0lmBxkDKQ-B447-MpvzcdZ7Mveen

    e) 1yNhyZSZtNoyWYHGZuL69Cl7iIKP-X1iK0xwsZRIHC9ShJJ47eveZWLB9ybtdQf1nzQXd0x-VyziQn7TlM2rqIXH0KZ6eM93Z4KXsX7s6st0gYJrRNI6LwG5gDVOgnk_zooCIYUR

    3-5

    a) 3-chloropentane

    b) 1-chloro-3-methylcyclohexane

    c) 5-chloro-2,2-dimethylhexane

    d) (1R,2R)-1-bromo-2-methylcyclohexane

    3-6

    a) Secondary

    b) Primary

    c) Tertiary

    d) Tertiary

    Alkene Nomenclature

    3-7

    E80xLBjSvt1FJSlXBA350gCXyG2wCcyAMwCHihvc7LsgNc-4YkH9P6xpzA5ar93NfUuT-wVjjBoHAXnZTChmLLARL-gaun-GOkM61FcNO_CrH7xuzKFzRzBU0ol7dpdoIvsQqqgI

    3-8

    6u3oFcxqGJLGFYT9vRocO65Dfy6tyxicoMHV3Wc-cn274NcENJOlTisMMY0Jos6wi7QzujxfHLshgYkXvaqnNdh8uB1oJOgQsZXUdS7SjpYa7yT5I5eT3lDvAmIw1MHV4bfPiReC

    3-9

    a) Z

    b) Neither

    c) E

    3-10

    Alkyne Nomenclature

    3-11

    a)

    bCl3UHFE15H5b6RD6kwrzZ6DhGLynY5hrTvmX9nAc_YugWcspOFBqQQ5RrOrPFxSyOUpEeMVbRGrcStU5Dd5YZxGi0qZKUB_0wtITG-ftw2vAJXZbW6DzsVfSMLGo3UH6V3vRlom

    b)

    gpcZiInUBqQeSZ2iwtCdzbrPZyLG-15hkJ-B9MfzzcJSo0kpyHptLtXpHAUzeswCfe_zd5dLzSrsFkzAVaZltDGDsnXl_53cRaGr9eKi1WLMY-eexsCCHiGMaiQQfivSip5GhbQt

    c)

    aqfJwmW957XpjPxcdHr3vVIep2I4V9UCoXG6AwKPoizLNtUf8a0rL98-LoO3IeUtkxCV2sUfZDUBs094TW4tZQ2tyGRSrXxukq7YcQmwlyyOvCzpz8sbEWkqW95sBdmr12cc1guf

    d)

    Dk7ncxEWpKSTPPhm3SUwZehkCup_mAHsJrlKsNdgIkqFkU61VVIcMJVWA3z38CwTkzXb9JtBesav2WVfWCXlnThhwSmra1IDFLg9ulQ8Imdc8f9j7YJDdq6i4gLwVi75lVcWRMka

    e)

    7bMm4LxNZdJBdbDrqLMrzPQdQf8vthY740ZNWO2Qm56SmqvDRGtQBIil39iRWJ7hHqnIHPGvPlcQK39ddhLolAMAyc9rS_7PAF3z5FQEXPccOK9c0u3GhJc40r5Zp7dvMln0C0TW

    f)

    ZKPW2KQtI9kw7qVwcQwFNJWQSvehSKKOcKgOy8E1Iaez_A1ZWs_3tKir_XTxlZzuABMzNUUjo7j64LUdtpkgaIWbsjdmpQDS6gggYJXaSKp34qGj2WjnLti7nZkUA-gLqXTPt8xm

    3-12

    a) 1-chloropent-3-yne

    b) 2,2-dimethyl-6-methyl-hex-4-yne

    c) cyclohexylhept-1-yne

    d) 4-bromo-2-chloro-3-methylnon-7-yne

    Alcohol and Phenol Nomenclature

    3-13

    a) Primary

    b) Secondary

    c) Tertiary

    d) Secondary

    3-14

    3-15

    3-16

    Ethers

    3-17

    Lz6uR7y7y2WeMVQgQtu9Nm4PO1C0fWLaRM6mrs4GfP4__oY32MR62hE-vDKZP7nGhxTW0clusedY0HU5cFYcEEp83y64ekmYGMoTfXtdyQjidlzIFs246-6hkAy4AoKzZSR6xmdL

    (g) oxydicyclopentane

    (h) 2-phenyloxirane

    (i) 1-cyclohexylethane-1-thiol

    3-18

    (a) (b) (c)

    3-19

    (a) diisopropylsulfide (b) 1,3-dimethoxybenzene (c) 2-Methyltetrahydro-2H-pyran (d) methyl 3-sulfanylbenzoate (e) methyl(phenyl)sulfide

    Benzene and its Derivatives

    3-20

    A – meta; B – para; C – ortho

    3-21

    1. 1,3-Dibromobenzene
    2. 1-phenyl-4-methylhexane
    3. 1,4-Dichloro-2,5-dimethylbenzene
    4. 2-methyl-1,3,5-trinitrobenzene. (Also known as trinitrotoluene, or TNT)

    13-22

    3-23

    ZEwFk3IwG72k6ewCBiAGPtsUSQ4AQBS6fJNOuGqOBqseXs2_3up_4TOttvL9K1WvHshpavwLynRjoFQoPKUJCf9FPDWYBNxDu7xZlKBYZTbP8mtCFjPt3DQC1YB9GbaBUWpUwaZL

    3-24

    XDgNQBtaqZq9D92cmoBCYzZtiHiL-RwozhKRbWIjLc4v0DI9rda325Kz9f-y3Bc-btxshb7mlrYGC2LTor9AIAWqxMCPrAL_a8_I2w4CkNmflrl7lOm0WGJJX_QnftduD-vO0x6_

    3-25 In order of priority: Benzoyl bromide > Amino > Nitro

    Aldehydes and Ketones

    3-26

    ktAg6YUM7C_r04tcygeM7NI_PuPpPaY1U9_tkY46Cx10wJc_2zyOv-uaDlw3UVR8FFgmX11Y-aQ-_QkQXBpNqKZFsmIlwmPy24vQxzVAN_5GZdj9GAzio9VXSI0h5c7_MQVbzCJf

    Amines

    3-27

    gcebzXDx0fZGHfClKOzx8CVeWpsU16d5lIk8yYCeWfoU1WYBMBTkprofbb_nyIq97RTJgXJ-_rwc9Y7FX47ZKh3Vebf9ycKmUiP5HMgA8MkIqXlXRdnIQDiVxxFCQqVIzm18oiLL

    Carboxylic Acids

    3-28

    Zr25liBLmwOIxjFOrIXzM8JYFCshU577Y4AFdPPfqP8CjEzegmozPRmH0azEeXCHLkZdZLvRgVMdwxyJ0xjry1mhNH-1HQ-KFoCVNO4ZLMyG5wCG3bSKypXn9TsWycPSRAyImwKN

    Carboxylic Acid Derivatives

    3-29

    1. 3-methylpentanoyl chloride
    2. 2-cyclopentylacetamide
    3. propyl 2-methylpropanoate
    4. cyclohexylbutanoate
    5. tert-butyl cyclopentanecarboxylate
    6. 1-methylbutylcyclopentane carboxylate
    7. N-methyl-3-butenamide
    8. (S)-2-hydroxypropanoyl phosphate
    9. propyl 2,3-dimethyl-2-butenethioate