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)
(c)
(d)
(e)
(f)
(g)
(h)
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)
b)
c)
d)
3-6 Classify each of the following compounds as primary, secondary, or tertiary alkyl halides
a)
b)
c)
d)
Alkene Nomenclature
3-7 Give the IUPAC name for the following alkene structures.
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.
3-10 Give the IUPAC name for the following structures.
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) b) c) d)
Alcohol and Phenol Nomenclature
3-13 Classify each alcohol as primary, secondary, or tertiary.
3-14 Give a systematic (IUPAC) name for each alcohol.
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.
Ethers
3-17 Give the IUPAC name for the following chemical structures.
(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
- p-chloroiodobenzene
- m-bromotoluene
- p-chloroaniline
- 1,3,5-trimethylbenzene
3-23 Give the IUPAC name for the following benzene derivatives.
3-24 Draw the following molecules given by their IUPAC nomenclature.
- 5-formyl-2-hydroxybenzoic acid
- 1,2-diethyl-3-fluorobenzene
- 4-amino-3-ethyl-5-methylphenol
3-25 Rank the functional groups on the following molecule in order of priority (highest to lowest).
Aldehydes and Ketones
3-26 For the following molecules, give the IUPAC nomenclature.
Amines
3-27 Draw the structures given by the following IUPAC names.
- 4-methylpentan-2-amine
- N-ethyl-N-methylpropan-1-amine
- 6-aminocyclohex-1-ene-1-carboxylic acid
- (dimethylamino)acetonitrile
Carboxylic Acids
3-28 Give the correct IUPAC nomenclature for the following compounds.
Carboxylic Acid Derivatives
3-29 Name the following compounds using IUPAC conventions
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)