3.15: Additional Exercises

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

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.

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).

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.

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.

Carboxylic Acid Derivatives

3-29 Name the following compounds using IUPAC conventions

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)