12 U Orgo - 1 - Hydrocarbon Nomenclature Worksheet 4y35m

Hydrocarbon Nomenclature Worksheet 1. How has the definition of “organic” changed over the past 200 years? 2. Describe the properties of a carbon atom that allow It to be the foundation of all organic compounds. 3. What does it mean for a hydrocarbon to be “saturated”? 4. Why does water not mix with liquid hydrocarbons? 5. What is the relationship between the number of carbon atoms and the boiling points of the alkanes? 6. Draw the following alkanes.

a) b) c) d) e) f) g) h)

nonane 2-methylpentane 1,3,5-fluorocycloheptane 3,3,5-trimethyloctane 4-ethyl-3,4-dimethylheptane cyclobutane 1,1-diethylcyclohexane 2-chloroethane

i) j) k) l) m) n) o) p)

methylcyclopentane 4-propyloctane 3-ethyl-3-methylhexane 2,2-dimethyl-3-propyloctane 3,3,4,5-tetramethyldecane 3,3,4-tribromononane 2-ethyl-3-propylcyclohexane 2-cyclobutylpentane

7. Name the following alkanes. H3C CH3

CH2

CH

CH

H3C

a)

H3C

CH3

CH

CH

CH3

CH3

CH2 CH

CH2 CH2

CH2 CH2 CH2 CH CH3 HC H3C CH CH2

CH3 CH

H2C

H2C

H2C CH3

b)

CH3

CH3

c)

CH3 H2C

CH2 HC

CH3 H3C

CH CH2

d)

CH3

CH2

CH3

CH

CH

CH2

CH2

CH2

H3C

CH3

CH2

CH2

e)

CH3 CH

CH

CH2

H3C

CH3

f)

CH3 H2C

CH3

CH H2C

H3C CH2 H3C

CH3

CH2

C

CH

CH3

CH

CH2

H3C

CH3

H2C

CH2

CH3

g)

h)

C

CH3

i)

H3C

CH3

CH2 C CH3 H3C

CH3 CH2

Cl H3C H3C

CH2 CH

j)

CH3

CH3 C

CH2

H3C

CH3

k) H3C

H3C

CH3 CH

CH

CH

CH2

H3C

C

l)

CH

CH C

Br

Cl

CH3

H2C

CH3 CH3

m)

CH2 CH

CH2 CH2

8. Draw as many structural isomers of heptane as possible and name them. 9. Are double and triple bonds between carbon atoms more or less reactive than single bonds? Explain. 10. Explain why no number is used in the names of ethene and propene. 11. Why are cis or trans isomers not possible around a single or triple bond? 12. Draw the following alkenes and alkynes. a) 5-ethyl-2-methylhept-2-ene b) hexa-1,3,5-triene c) 3,4-dimethylcyclohexene d) but-1-yne

e) f) g) h)

4-methylpent-2-yne 2-methylhepta-1,5-diene 3-methylhex-2-ene 3-propylhept-2-ene

Cl

i) 4-ethyl-2,5-dimethyloct-3-ene j) 2-methylbut-1-ene k) 4-ethyl-4,5-dimethylhex-1-ene

l) 2,5,7-trimethylnon-3-yne m) 3,5-diethyl-3,4,7,8-tetramethyl-5-propyldec1-yne

13. Naming the following alkenes and alkynes. Don’t forget about cis vs. trans! CH3

H3C

C

C

CH

H3C

CH

H2C

a)

CH2

CH

H2C C

CH3

b) H3C

CH3

CH CH CH

CH2

CH2

CH CH2

CH2

CH3

H3C

c)

CH2 CH3 CH3

CH2 H3C CH

d) H3C

CH2

CH

CH

H2C

CH2 C

CH2

CH H2C

CH3

e)

CH3

C

CH CH3

H2C CH3

f)

CH2 CH2

H3C

CH2

g) H3C

h)

H3C

CH2 C

CH C

CH2

Cl C

Cl

CH2 CH3

i)

CH2 H3C

CH CH2

CH

CH3 C

CH3

H2C CH2 CH3

C CH3

CH H3C

j)

CH2

CH

CH2

H3C HC

CH2 HC CH2

H3C

H3C

HC

CH

CH

CH2

k)

CH

C H3C

H2C

C CH2

CH2

l) H3C

CH CH2

CH3 CH2

14. Draw as many structural isomers of hept-1-ene as possible. 15. Determine the chemical formula for the following hydrocarbons: a) an alkane with 14 carbons c) an alkyne with 33 carbons b) an alkene with 25 carbons d) a cycloalkane with 9 carbons

16. The names are incorrect in the chemicals below. Draw each structure and rename correctly. a) hex-4-ene e) 3-methylprop-1-yne b) 3-propylhept-5-ene f) but-3-yne c) 3,3-dimethylprop-2-ene g) 2methylpent-3-yne d) 3-methyl-4-ethyl-4-propyl-hex-5-ene h) 2-methyl-4-propyl-4-ethylhex-5-yne 17. Describe the bonding structure in benzene. 18. Compare cyclohexene with benzene in of reactivity and structure. 19. Draw the following aromatic hydrocarbons. a) 1,2,4-trimethylbenzene b) 1-ethyl-2-methylbenzene

c) 3-phenylpentane d) 1-4-dimethylbenzene

e) 3-methyl-4-phenyloctane f) 1,3-diethyl-4-methyl-2-propylbenzene

g) 2-phenyl-5-propyloctane h) 4-ethyl-2-phenyloctane

20. Name the following aromatic hydrocarbons. CH2

H3C

H3C

CH

CH

HC

CH2 CH

a)

C

CH2

CH3

H3C

CH2 CH2

CH3

CH2 CH2

CH

CH3

b)

c) CH3 CH2 CH2 HC

H3C

CH2

CH3

CH3

CH

CH2

CH2

CH2

H2C

d)

CH3

e)

f)

CH3

CH3