Download Chemistry 322 Experiment #3 Data Sheet

Chemistry 322
Experiment #3 Data Sheet
NAME: ________________________________________________
1. Retention Times (in minutes) of Alkenes in Product Mixtures
2. Relative Peak Areas of Alkenes in Product Mixtures
SECTION: ________
3. Write a mechanism for the dehydration of 3-methyl-3-pentanol and indicate which products
are major and which are minor isomers.
4. Flow Chart. Fill in the empty rectangles with the appropriate cations. In the empty ovals, fill
in the appropriate methylpentene structures.
H+
OH
80-100 oC
80-100 oC
(E and Z)
5. In the first part of this experiment, you performed Lucas tests on several alcohols.
a) Write a complete mechanism for the reaction occurring between the Lucas reagent and tbutanol.
b) Benzyl alcohol and 1-butanol are both primary alcohols, yet they behave differently
under Lucas test conditions. Clearly explain the difference in reactivity between these
two alcohols. It is NOT enough to say that "X is more stable than Y" - you have to
explain why!
6. A small amount of 3-methyl-2-pentene can form during the dehydration of 2-methyl-3pentanol. Write a reaction mechanism that accounts for this product. Consult your lab
manual for guidance.
Chemistry 322
Experiment #3 Data Sheet
NAME: ________________________________________________
1. Retention Times (in minutes) of Alkenes in Product Mixtures
2. Relative Peak Areas of Alkenes in Product Mixtures
SECTION: ________
3. Write a mechanism for the dehydration of 2-methyl-2-pentanol and indicate which products
are major and which are minor isomers.
4. Flow Chart. Fill in the empty rectangles with the appropriate cations. In the empty ovals, fill
in the appropriate methylpentene structures.
OH
H+
80-100 oC
80-100 oC
(E and Z)
5. In the first part of this experiment, you performed Lucas tests on several alcohols.
a) Write a complete mechanism for the reaction occurring between the Lucas reagent and tbutanol.
b) Benzyl alcohol and 1-butanol are both primary alcohols, yet they behave differently
under Lucas test conditions. Clearly explain the difference in reactivity between these
two alcohols. It is NOT enough to say that "X is more stable than Y" - you have to
explain why!
6. A small amount of 3-methyl-2-pentene can form during the dehydration of 4-methyl-2pentanol. Write a reaction mechanism that accounts for this product. Consult your lab
manual for guidance.