Virtual Chem Lab: Studying Alkene Reactions with 1-methylcyclohexene (25 points + 3 bonus) Name________________________

1. Fill in the data below for each reaction. Fill in the observed TLC plate for each completed reaction. (Tip: Because the reaction should be complete – there should only be one spot in each lane). For each reaction, calculate the Rf value for the starting material and product and record this in the table below each corresponding TLC plate. Additionally, for each reaction, record the reaction time (in minutes). (10 points)

Rf Starting Material
HCl
Et2O Br2
Et2O Br2
H2O H2O
H2SO4 CH3CH2OH
H2SO4
Rf Product
8 10 6 4 5
Time (in minutes)
180 minutes 4 minutes 13 minutes 56 minutes 81 minutes

2. Write the name of the product formed for each reaction (as provided in the VCL software). (5 points)

Reaction:
Product Name:
1: Hydrohalogenation
1-Chloro-1-methyl-cyclohexane
2: Halogenation
Trans-1,2-Dibromo-1-methyl-cyclohexane
3: Formation of a halohydrin
Trans-2-Bromo-2-methyl-cyclohexanol
4: Hydration
1-Methyl-cyclohexanol
5: Etherification
1-Ethoxy-1-methyl-cyclohexane

3. Complete each of the following sentences by circling the bolded word(s) that makes the statement true. (3 points)

a. In the TLC of Reaction 1, the starting material product was more polar. (circle 1)

b. Reaction 1 2 3 4 5 used sulfuric acid as a catalyst. (Circle all that apply)

c. Reaction 1 2 3 4 5 took the longest to complete. (Circle 1)

4. Draw the product to each of the 5 reactions in this lab. Be sure to indicate stereochemistry if the product has any. (2 points each, 10 points total)