Worksheet 4
Organic Naming and Organic Reactions 1
1. Give the IUPAC name (ignore cis-trans isomerism)
a) CH3 – CH = CH2
b) CH3 – C = C – CH3
Br Br
c)
Cl
d)
Cl – C – CH2 – CH = CH2
CH2
CH3 – CH2 – C – CH3
Cl
e)
CH3
f)
H3C
CH2 = C – CH2 – CH – CH3
g)
a)
c)
e)
g)
Cl
2. Draw the structural formula for
ethylene (ethene)
b) 2 – pentene
2,4 – dimethyl-1-pentene
d) 1,2-dimethylcyclohexene
2,4-dibromo-6-methyl-3-octene f) 2,5 – heptadiene
1,4 – cyclohexadiene
3. Give the following IUPAC name:
a) CH2 = CH – CH = CH2
b) CH3 – CH = CH – CH =CH2
c)
d)
Br
CH3 – CH = C = C – CH3
4. The compound 1,1 – dichloropropene is shown below:
Cl
C = CH – CH3
Cl
a) Why isn’t this compound called 3,3 – dichloropropene
b) Is there a compound with this name. If so, draw its structural formula.
c) Is there a compound 2,2 – dichloropropene?
5. Define addition reaction. Write the equation for any addition reaction to propene.
6. Write structural formulas for the principle reaction products when ethene,
CH2 = CH2, reacts with
a) Cl2
b) H2 + Pt
c) HBr
d) H2O + H2SO4
e) Br2
7. Write structural formulas for the principal reaction products
a) CH3 – CH = CH2 + H2 
b) CH3 – CH = CH2 + Br2 
c) CH3 – C = CH2 + HBr 
(Pt catalyst)
CH3
+ H2O 
d)
(H2SO4 catalyst)
e) CH3 – CH = CH – CH3 + HBr 
f) CH3 – C = CH – CH2 – CH3
+
H2O 
(H2SO4 catalyst)
CH3
8. Show how to make the following compounds starting from propene,
CH3 – CH = CH2 (write equations)
a) CH3CH2CH3
b) CH3 – CH – CH2
c) CH3 – CH – CH3
Br Br
d) CH3 – CH – CH3
Br
OH
9. Write the structural formula for the principle reaction product, if a reaction takes
place. Where there is no reaction, say so.
a) CH3 – CH = CH – CH3 + Cl2 
b) CH3 – CH = CH – CH3 + I2 
c) CH3 – C = CH2 + H2 
CH3
d)
H3C
+ HI

10. Write structural formulas for all possible addition products when HBr is added to
each of the following. In each case predict which of the possible products is
actually formed, in accord with Markovinkov’s rule:
a) CH3 – CH = CH2
c) CH3 – C = CH – CH3
b) CH3 – CH2 – C = CH2
CH3
d) CH3 – CH2 – CH = CH – CH2 – CH3
CH3
e)
11. Could you make 1 bromopropane from propene? Explain.
12. Assume that you are given a liquid that could be either cyclohexane or
cyclohexene. What simple test could you perform to tell which it is? Describe
exactly what you would do and what you would see in each case.
13. Write the structural formula for the principle reaction product, if a reaction takes
place. Where there is no reaction, say so.
a)
+ I2

+

b)
Cl
Br2
c)
+ CH3CH2Cl
d)
+ HNO3


Worksheet 4
Organic Naming and Organic Reactions 1
Answers:
1a) propene
b) 2,3-dibromobut-2-ene
c) 4,4,4-trichlorobutene
d) 2-methylbutene
e) 4-methylpentene
f) 3-methylcyclopentene
g) 4-chlorocyclohexene
2a) H2C=CH2 b) CH3CH=CHCH2CH3 c) H2C=C(CH3)CH2CH(CH3)CH3 d)
e) CH3CHBrCH=CBrCH2CH(CH3)CH2CH3 f) CH3CH=CHCH2CH=CHCH3 g)
Br
Br
3a) 1,3-butadiene
b) 1,3-pentadiene
c) 2-bromo-2,3-pentadiene
d) 1,3-cyclohexadiene
4a) lowest numbers needed for substitute
b)
c) No
6a) CH2ClCH2Cl
b) CH3CH3
c) CH3CH2Br
d) CH3CH2OH
e) CH2BrCH2Br
7a) CH3CH2CH3
b) CH3CHBrCH2Br
c) CH3CBr(CH3)2
e) CH3CH2CHBrCH3
f) CH3COH(CH3)CH2CH2CH3
8a) + H2
b) + Br2
c) + HBr
d) + H2O
9a) CH3CHClCHClCH3
b) CH3CHICHICH3
c) CH3CH(CH3)2
d)
10a) CH3CHBrCH3
b) CH3CH2CBr(CH3)2 c) CH3CH2CBr(CH3)2
Cl
Cl
d)
OH
I
d) CH3CH2CH2CHBrCH2CH3 e)
Br
11. No. Markovinkov’s rule
13. a)
b)
c)
Cl
I
Cl
Cl
Least
Likely
Br
Br
Br
d)
CH2CH3
NO2