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3.15: Additional Exercises

  • Page ID
    122578
  • Alkane Nomenclature

    3-1 Draw the structure for each of the following compounds

    (a) sec-butylcyclohexane

    (b) 2,2,7-trimethyloctane

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

    (d) 1-cyclopropylbutane

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

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

    (g) trans-1,4-diisopropylcyclohexane

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

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

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

    (k) Norbornane (Bicyclo[2.2.1]heptane)

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

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

    (a) (CH3)2CHCH2CH2CH(CH2CH3)CH(CH3)CH2CH3

    (b) 6ijovGCcTCQk6Lq8om0PnPHtJNa5zLm34a9hwNDciQzvo_6NAhPsmt5QED6SxQ-uuYcUq4R8OExQEN3cwoRqELJiA5vr_ugJgd8kuuiGXVvNfP_GyNVSmlG7n7PB6mFWs9WCrzh1_9y-zwORVQ

    (c) t1YJX9kQk_YCGmDvcHezeYYVaj8OX7XE0YgeCj6i0An8_m8j9JI7C9VSV-tvTSWFFnP5cMER4yglU0eOrKxQJ0eax02x3lNE5TfIEaliZxu5PVHeBAGjJilKHBI_mVVwrn3We8fARYE8y-48PA

    (d)SYp9GalYfoO1hpwabb3iGQbR0_ccGzSrj7fS3Po5xUS5mmPKCHkYFU3q-kM1Ylx2b5oxtUJ32t2hsSZaY5YZkKuzkt9xkouETQF__9pRvj34ATaiM6lX_mhZqxtDDIfYjgJPuNlWusL5aU-DLg

    (e) nyBPuCHM3flCAEIR2wb-NygnuMArBZZ-UVb8NFYv905_miwo0FRxGz4UcCqIRqI0WWG7k2FSGTMr5NDLCUz8EVaqyhlhbHMcrTwL0UEZgTptYDxWBAAGUaX8ZuMqFWc_kQEzrwdTgqZarEezOw

    (f) SO8FDbHok0kin77ttfuvv7VkzYBtsyfJBgZbEUCwDqAd4BkvJ0zWRbgrTzoKIAEz3zHzwwMHbH94yIxTTITUJPE3B2ZzLWZsNmmL7urBfDvVllBux0BOEXGqJKtF0KjdPGweTkzBKoO6m4bcVQ

    (g) Sd6xBiHfRcMZvm8rKbqnZfH1LERrd6GBdrkWySephadVlGz7CACFpzHZSx4rxdausvkQ2fz2V543r5IsyDsKSQlYnW9X4lQb61M2AhyEfYP_lqkAYpIGICPQrE_yQ2hmSDmotXPshudoiX6F1Q

    (h) OH382OOvIsO_8N3lygfYx_7e6TKkkvTPsYD8lSU6rsVP39wUdVKixNeDTs8K4O4aGJMd7TcH_tAuc0iEgq4zy1Une5WyXtw8M33WSRq2sV-7LvdCim2VHXlhkkEbD_KB8yWSN7jgEJt2KR077g

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

    (a) 2-ethyl-3-methylhexane

    (b) 2-isopropylpentane

    (c) 2-bromo-5-isopropylheptane

    (d) 4-ethyl-3-isopropylheptane

    (e) 2,4-trimethylpentane

    (f) 1-chloro-2-ethyl-5-methylcyclohexane

    Alkyl Halide Nomenclature

    3-4 Draw the structures of these following compounds

    a) 2-chlorohexane

    b) 1-bromo-2-chlorocyclopentane

    c) Isobutyl chloride

    d) 5-chloro-2,3-dimethylhexane

    e) (2S) 2-bromohexane

    3-5 Give IUPAC names to the following compounds

    a)_oEsvLPObmJByTrabep0HNLFfADLsWxaCtcnspO-86mASTEkrkSBWVg3ttS8-0e8sAZDsJ6fIX8_P6Qq41n2eQ0VpfVxa-91MHr5cOdQi72BUJdvYS1fXNUjH8zwzPKomvsLx1iO

    b) e1jVwEJ7_eiZF5CjFulA-xnibaE-bxGmO3t_wGJ0yBF6DkSE41LJ9e0rNkJDShYC_x1-y4QWGR_odneJz357D8aRLMHWgVTsGQPtZ6HslHdWe-Pgw6gChCyZfnmhdLc0hpSBgWS8

    c) kls6om_QnCgFmnSur-OHbYaz1GcAfGAcseFwZ_Gm_xs5OQ0KqHSg21rOOJSEuWoNGdibx3wAJJeNGUZxDKHhk6QyREimRyy-CmC65RWYbnn528pDTFLh-ssn7dHZhL_GIYDj9jjP

    d) y8IeqV-pxp99OWCQC5BmSdaFH2EgJkzC3wKvlRDuTDsfEhyus67SNUrdHS3OirO36ByAyOY3HPr9NxmwujydJWzmE97SnbFo3QE05Z2vl2jgRnPvlvC8WN7miy7lNdTq2n7WKONR

    3-6 Classify each of the following compounds as primary, secondary, or tertiary alkyl halides

    a)

    b) 1a7gpg89DTW1B7JN4M98prbNo3xxA8F-AJWIM8rlygCqFylNN6Bji5ctLazRLFLTfsaBKKYgw-a9k7EcmgjtNVYNMHBbksH5y-BheQHUf6Cxt34G5Amhfza6AWZnEeSuEdDSLnCU

    c) aXhgHZEqq2FQg8e9NKK5s2telC3W3TZn0RQSyrnekJg_dNVpaYDb3rWVPWrplNf4uFG6EXaR6sFhv6AcYhOmQu6DK3jM2eZT1xkha3bC0qA4LBeaKdUbeXhvdN4L1bHX1VqmO-8T

    d)5q_WZJ0ACQ00k0yh5iWES0ggnZfTGyzjyL-MLwitQSgscRW1p1MTW6TsaLpqcr1Oi1F1b9CTYEdn2u6x5SHrGEhNDUSOoIfZZRRy4xU86yIySIrZg1FkDdnTWsVrrmytgHbLZ5m-

    Alkene Nomenclature

    3-7 Give the IUPAC name for the following alkene structures.

    dYit_WoCvAOgJymjb0FLu16tnjNCtt6XoxkpHtaqeMEMg4jvYtFZMmQ7APbBdyTGEEwMz83AVam2-Lr3zp6GJA2RZVN5K2c3y0s4FjGZW0tq3ExE27jXm1IUTwYdbmpKi999ttKi

    3-8 Give the structures of the following compounds.

    a) [1,1'-bi(cyclohexan)]-1-ene

    b) 2,3-dimethylbut-2-ene

    c) (4E)-4-ethylidene-2-methylhept-1-ene

    d) [(1E,3E)-hexa-1,3-dien-1-yl]cyclopentane

    3-9 State whether the following compounds are Z, E, or neither.

    ZXC3VtQYabB5Yl2SFs_NBaYCURCvvq4GyBv7Esvv4E-NAEO6LpnLykJjB2JXLQP3ZusKKc7QmSise6r-HUrHKNpl7tFyd9a4ps_6KjivSCm8YNW6GNDs9x4weWT3I9Cg-cUK5cn_

    3-10 Give the IUPAC name for the following structures.

    bcRLqQYjstVcBu-TRDPlSYYS3d13M_Bcfa1fXRQTGcKTkWNvPT70vs7r9BbSdStWXF5P-WJTwvB6LqjmPY5E-bU20zsOgweBayu4zUWp9VkHjjTP7w8EmVAZ1vtOx4vQZT5csU8h

    Alkyne Nomenclature

    3-11 Draw the bond-line for these following compounds:

    a) 3-hexyne

    b) 2-bromo-5-octyne

    c) 3,3-dimethyl-6-decyne

    d) Cyclopentylacetylene

    e) 2-chloronon-4-en-6-yne

    f) 2,4-heptadiyne

    3-12 Give IUPAC names for the following compounds

    a) aWkv5MlE05zT8P3MotQE8j-VNdg2amA7oAFnkqamv4iDcHfoiMIrhdUgvu9KFRnqofpNE1Xmb97z1KFi1IabV3eaAhrBn2kLsNHQoAL69EHuP9QUS_fOt7S9Vf4MgS0j9NG07zUv b) Dj78ZJtDA3r3rcwu9kK1RvNF6Tyqd3osXPsqpEzgO5nKiohKw6PSMakS_q5O117T7S8uTaLopD-FWhNpLrT5M1ySck2ANPV38x8YniuoZF_Jf7SRL_ERvQKPBqxZfT3ZEbgC8rVV c) o-AKXH3a2hzrueNwb4x6NjEUCpUT2bvBuqtfmQeGU64vbSpCAgXGahi3AyUZs4RTpt4nfbr_BE1-jr8Shpb0Je5inuNBfTH1_WOJ7Mo7H9NWD45HSTBRBuo3V0l5XBFkwKzuoGou d) G4fLBx3Q_44__Ci1enhlYZ2AmyLxcoN13D3yQ8eEFcesT_9s60GLbVa6Sif3kZJvJuQM-Aa9VbuxuhdmtAyy-xsNJYejH9WZpVFGBzZ1BnOZ97SBBrF_Zs7XWfNA25sIdE6c8G4I

    Alcohol and Phenol Nomenclature

    3-13 Classify each alcohol as primary, secondary, or tertiary.

    8onm8Bn_TM14J5h6nAQ-EYcwnkk6inoGHk6wQkENvR26qO5Zz6JB1jQ65Y9fbY3dVLpL0P5g4YylCuHwbLNMMzV6Sdx_WXdDV-nKnIUR9zgGbx8xtJxUPkWnHo5mNHXmXxyevsg5

    3-14 Give a systematic (IUPAC) name for each alcohol.

    IeAcWt0_SWlE9dGd4bV4YYVBh8PvKT2vBhBZwoiS1RJJPcvNiND36IX-hsfY82mD23kkexFAyfjf_UOLCSmpi1-XO1Y_ZoGHCQohxN9f_tOpz9LI6vXivNeS7Fx_6u7ccXefIJAy

    3-15 Draw the structures of the following compounds.

    a) 2-methylhexan-1-ol

    b) 2-methylpentan-2-ol

    c) 2-chlorophenol

    d) 4-(chloromethyl)hexan-1-ol

    e) cyclopent-2-en-1-ol

    f) 3-bromo-2-(2-bromoethyl)pentan-1-ol

    3-16 Give a systematic (IUPAC) name for each phenol.

    18VAIxRimhWL4WFL0bpBwUTiYai-6EVWWq6cQAI-mlDYYerbggLA3bY0BST5uJ_yW4eBi7ZUkH-9O13RVWwJn0BJZKVXhiGElxmm0VqGvgJ5nNHsDs1GH-OMFNEGU87tyUqEib58

    Ethers

    3-17 Give the IUPAC name for the following chemical structures.

    WLUKESXrzNUPObxyHUoK0fCT6RPJ7ksuf3Hzy0OvL3phpDvE-P7AgT58DiRKM_clDY2ga-s1Px7ICuVvgJ930E5h5--_egjoa-Z-kklnqrbjARN3NPzFLD3awC2F1AbT_Nj4tOQP

    (g) (h) (i)

    3-18 Draw structures of the following.

    (a) 3-isopropoxypentane (b) 1-(4-chlorophenoxy)-3-methylbenzene (c) 2-(tert-butoxy)-2-methylpropane

    3-19 Name the following ethers and sulfides.

    (a) (b) (c) (d) (e)

    Benzene and its Derivatives

    3-20 State wither the following is para, meta, or ortho substituted.

    3-21 Name the following compounds.

    3-22 Draw the following structures

    1. p-chloroiodobenzene
    2. m-bromotoluene
    3. p-chloroaniline
    4. 1,3,5-trimethylbenzene

    3-23 Give the IUPAC name for the following benzene derivatives.

    J9MvSWGfW0VjmzpaI8kSqy-LxMk1sghwVwFAqueJGC11NCk7cOcSl1KnQqDXKlcF76kQz1cUC0C-F2m0xPunOf360egdgh7GLZrpJ_aCwz1_Ga1YyvREdg-cdXGdYjcoknaydcsI

    3-24 Draw the following molecules given by their IUPAC nomenclature.

    1. 5-formyl-2-hydroxybenzoic acid
    2. 1,2-diethyl-3-fluorobenzene
    3. 4-amino-3-ethyl-5-methylphenol

    3-25 Rank the functional groups on the following molecule in order of priority (highest to lowest).

    RhduLWuQEg6tIhFWUHXIcVeJJNZZDjGcGYHdbOFwhYV-fgBPzNQ8fslzmMhAfUKjoZGQe-PFhQiqKm9Z7rrcD_tN5erNVaulS-L3dGZsIFEzHqfRgNZ9bNAk5AoWW9hX96JVF0VG

    Aldehydes and Ketones

    3-26 For the following molecules, give the IUPAC nomenclature.

    E-Qexk6nCE7h_p3DtmgkyVCkgZj8DQnTfyQDDFjFOryzFyQI3e07CacE7l6gEyJM1D_D7pAs8EVSnXpd7RwYFVg36U0hj6WVcZkDqF9MYTApG-FNQ_9H22fBjIppTdOswdn09q4i

    Amines

    3-27 Draw the structures given by the following IUPAC names.

    1. 4-methylpentan-2-amine
    2. N-ethyl-N-methylpropan-1-amine
    3. 6-aminocyclohex-1-ene-1-carboxylic acid
    4. (dimethylamino)acetonitrile

    Carboxylic Acids

    3-28 Give the correct IUPAC nomenclature for the following compounds.

    2hbp5ISop-9Qs2Nv1m_Khh6cAn_XHD-VxD4GvLrUZx9obQctHEz0b_LFRDeN0pLfXbswtLNX-9LOj3pzJiZGZkE7Aut4PYBfIxGy0RPlU2Z1xxaQvOOPC8juyCHXjHOUKjbLGSJR

    Carboxylic Acid Derivatives

    3-29 Name the following compounds using IUPAC conventions

    (a)

    (b)

    (c)

    (d)

    (e)

    (f)

    (g)

    (h)

    (i)