Unsaturated hydrocarbon reactions worksheet (addition reactions)
For the following reagents, determine the: type of reaction, (hydrohalide addition, nonpolar (halogen)
addition, hydrogenation, hydration (acid catalyzed addition of water), free radical addition), whether a
carbocation is formed or not, if its syn/anti addition, or Markovnikov/anti-Markovnikov.
H-Cl
HBr/ROOR (peroxide)
X2/CCl4
H2/Pt, Pd, or Ni
H3O+
Cl2/AlCl3
Dilute H2SO4
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Name/Description:
Markovnikov/anti-Markovnikov:
Syn/anti- addition:
Carbocation formed?
Predict Products for each of the following. If there is more than one possible product, show all possible
products, but identify the major product.
The acid-catalyzed hydration of 1-methylcyclohexene gives 1-methylcyclohexanol. Draw the complete
step-by-step mechanism for this reaction.
Show the complete step-by-step mechanism for the addition of HBr to 2-methyl-2-hexene. If there is
more than one product, include them, identifying the major product.
When 2-methylpropene reacts with water and an acid catalyst, only one product alcohol is observed:
(2-methyl-2-propanol).
a. Draw the structures of the two intermediate carbocations that could form from the protonation
of 2-methyl-propene. Which is more stable (has lower energy)?
b. Draw the mechanism for this reaction show the formation of the more stable product.