Naming and drawing of organic compounds

Part II.15.03.2018

1.Write IUPAC names for following compounds and calculate molecular formulas:

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2. Draw the skeletal formulas corresponding to the following names. If you find the name is incorrect, write the correct systematic name. For each skeletal formula calculate the molecular formula.

  1. 2-(4-chloro-2-methylphenyl)pentane
  2. 4-bromo-3-methoxybutan
  3. 1,2-dimethoxy-1,4-hexadiene
  4. 3-(2-nitrophenyl)heptane
  5. 4-Nitro-2-cyclopropyl-5-cyclooctene
  6. 2-Ethoxy-4-tert-butoxy-1-nitrobenzene
  7. 5-Neopentylhexa-1,3-diene
  8. 4-Nitro-5-methoxycyclododecene
  9. 3-Bromo-1-ethoxynon-4-en-8-yne
  10. 3-Phenoxy-2-chlorooct-7-yne
  11. 3-sec-Butyl-4-chloro-1-metylenocycloheptane
  12. 4,6-Dimethoxyundeca-8,10-diene
  13. 4-(2-bromophenyl)-6-allylpentadecene
  14. 3-(4-Isopropylphenyl)-2-chloromethylpent-1-ene
  15. 3,4-Dimethoxynitrobenzene
  16. 4-(3-Trifluoromethylphenyl)-11,13-dibromotridec-1-ene
  17. 2-Ethyl-5-methylhex-3-ene
  18. 2-Cyclohexyloxy-5-phenyl-3-undecene
  19. 5-tert-Butoxy-4-bromoheptane
  20. 7-Cyclopentyl-5-nitro-2-octyne

3. Convert the following linear fomulas into skeletal structures as in example:


a)(CH3)3CCH(CH3)CH(C2H5)CH2CH2CH3

b)C6H5(CH2)6CH(CH3)2

c)(cyclo-C5H9)C(CH3)2CH2CH2CH2CH(CH3)2

d)CH3CH2CCCH2CH2CHCH2

e)CH3(CH2)6C(C2H5)2CH2CH2CH2CH2(cyclo-C3H5)

f)C2H5C(CH3)CHCHO

g)CH2CHCH2CH(cyclo-C6H11)CH2CH2CCH

h)CH3(CH2)8COOCH3

i)CH3CH2C(CH3)C(CH3)CH2CH(CH3)CH2CH2CH3

4. Convert branched alkyl groups C3-C5 into skeletal form like in example shown:


a)CH3(CH2)2CH2- butyl (Bu, n-Bu)

b)(CH3)2CHCH2- isobutyl (i-Bu, iBu)

c)CH3CH2CH(CH3)- sec-butyl (s-Bu, sBu)

d)(CH3)3C- tert-butyl (t-Bu)

e)CH3(CH2)3CH2- pentyl

f) (CH3)2CHCH2CH2- isopentyl (isoamyl)

g)CH3CH2 (CH3)2C- tert-pentyl (tert-amyl)

h)(CH3)3CCH2- neopentyl

5. Circle the functional group in every structure and give the general description of the compound like in example:



6. Propose skeletal structures for compounds that satisfy molecular formulas (there is more than one possibility in each case). Name the functional group in every structure you wrote.

a) C5H12b) C3H7N c) C3H6O d) C4H9Br e) C4H8O2f) C6H7Cl g) C3H7NO

h) C6H12i) C5H8Cl2j) C4H8S k) C3H7NO2l) C7H5N m) C4H7ClOn) C3H4O.

o) C5H10O2p) C4H9Nq) C5H6Or) C5H10Os) C4H10O2t) C7H5BrOu) C5H7N.

7. Draw structures corresponding to the IUPAC names:

a) 3,4-dimethylnonane, b) 3-ethyl-4,4-dimethylheptane, c) 2,2-dimethyl-4-propyloctane, d) 2,2,4-trimethylpentane, e) 1,1-dimethylcyclodecane, f) 1,2-dichlorocyclopentane, g) 3-cyclobutylhexane, h) 1,4-dibromocycloheptane, i) (1-methylpropyl)cyclobutane, j) 2-methyl-1,5-hexadiene, k) 3-ethyl-2,2-dimethylhept-3-ene, l) 2,3,3-trimethylocta-1,4,6-triene, m) 3,4-diisopropyl-2,5-dimethylhex-3-ene, n) 4-isobutyl-1-methylcycloheptene, o) 3,7-dimethyl-1,3,6-octatriene, p) 4-ethylcyclodec-1,3,5,7-tetraene, q) 4-methyl-1,2-penta-diene, r) p-bromochlorobenzene, s) m-chlorotoluene, t) p-bromoethylbenzene, u) o-bromoethylbenzene, v) 1-methyl-3-phenylcycloheptane, w) ortho-chloroisobutylbenzene, x) 1-fluoro-2-propylbenzene, y) p-iodonitrobenzene, z) ethynylbenzene.

8.The following names are incorrect. Draw structures they represent and provide correct IUPAC names:

a) 1,1-dimethylpentane; b) 3-methyl-2-propylhexane; c) 4,4-dimethyl-3-ethylpentane; d) 5-ethyl-4-methylhexane; e) 2,3-methylhexane; f) 3-dimethylpentane; g) 1,5-diethylcyclopentane; h) 2-ethyl-1-methylcyclobutane; i)1-iodo-2-ethyl-3-bromocyclooctane; j) 2-methyl-2,4-pentadiene; k) 3,6-octadiene; l) 3-methylene-1-pentene; m) 5-ethyl-4-octene; n) 3-propyl-3-heptene; o) 3-vinyl-1-propene; p)1-sec-butyl-3-cyclooctene; q) 1,3-dichloro-4-cyclopentene; r) 2-bromo-3-chlorobenzene; s) 4,6-dinitrotoluene; t) 4-bromo-1-methylbenzene; u) 2-chloro-p-xylene; v) 2,4,6-tribenzylbenzene; w) 5-methoxy-1-methylbenzene; x) 1-chloro-5-bromo-3-nitrobenzene.

9. Find structural formulas of following compounds known under common names. You can try to provide their IUPAC names but it is better to learn and remember these simple structures and their trivial names.

1) acetylene, 2) acetone, 3) acetonitrile, 4) acetophenone, 5) allyl alcohol, 6) acetamide, 7) acrolein, 8) methyl acrylate, 9) benzaldehyde, 10) acetanilide, 11) acetaldehyde, 12) aniline, 13) glyceraldehydes, 14) butyraldehyde, 15) acetic acid, 16) tert-butanol, 17) ethyl acetoacetate, 18) cinnamic aldehyde, 19) isobutyraldehyde, 20) formaldehyde, 21) salicylaldehyde, 22) isobutanol, 23) sec-butanol, 24) n-butanol, 25) benzyl alcohol, 26) isopropanol, 27) neopentyl alcohol, 28) tert-amyl alcohol, 29) benzamide, 30) benzophenone, 31) benzonitrile, 32) benzylamine, 33) chloroform, 34) dibenzylideneacetone, 35) acetyl chloride, 36) acetic anhydride, 37) succinic anhydride, 38) maleic anhydride, 39) phthalic anhydride, 40) benzoyl chloride, 41) benzyl bromide, 42) benzylidene chloride, 43) benzylidyne chloride, 44) methylene chloride, 45) pyridine, 46) ethylene, 47) benzylideneacetone, 48) tetrahydrofuran, 49) dimethylformamide, 50) glycerol, 51) glycine, 52) succinimide, 53) isoprene, 54) jodoform, 55) ketene, 56) allene, 57) vinyl acetate, 58) o-xylene, 59) p-cresol, 60) cumene, 61) adipic acid, 62) anthranilic acid, 63) benzoic acid, 64) glutaric acid, 65) fumaric acid, 66) -naphthol, 67) caproic acid, 68) caprylic acid, 69) caprinic acid, 70) malonic acid, 71) toluene, 72) lactic acid, 73) lauric acid, 74) mandelic acid, 75) oxalic acid, 76) menthol, 77) stearic acid, 78) tartaric acid, 79) valeric acid, 80) -naphthol, 81) vanillin, 82) ethylene glycol, 83) phthalic acid, 84) salicylic acid, 85) sulfanilic acid, 86) allyl bromide, 87) chloral, 88) cinnamic acid, 89) succinic acid, 90) maleic acid, 91) styrene, 92) pyruvic acid, 93) vinyl chloride, 94) acrylonitrile, 95) benzene, 96) decalin, 97) pyran, 98) formic acid, 99) p-toluenesulfonic acid, 100) thiophene, 101) furan, 102) pyrimidine, 103) purine, 104) pyrrole, 105) imidazole, 106) myristic acid, 107) palmitic acid, 108) naphthalene, 109) phenol, 110) quinoline.

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