Oscar Wu

Cameron Lopez
Shiva Moaven
11-28-17
CHEM 3105

Experiment 11
Results
IR Spec
C-H sp2 = 3022.70 cm-1
C-H sp3 = 2933.92 cm-1
C=C = 1652.46 cm-1

Initial conditions
Flask= 161.0758 g
Flask + cyclohexanol = 168.1927 g

2nd distillation results

Container = 131.3636 g
Container + distillate = 134.6095g

Calculations
Cyclohexanol (starting) = 168.1927 g - 161.0758 g = 7.1169 g
Cyclohexene (product) = 134.6095g - 131.3636 g = 3.2459 g
3.2458 g/ 7.1169 g x 100% = 45.6% yield

Discussion
The experiment in converting cyclohexanol to cyclohexene was a success. There exists a C-H sp2
frequency at 3022.70 cm-1, a C-H sp3 frequency at 2933.92 cm-1, and C=C frequency at 1652.46 cm-1. All
these bonds exist in cyclohexene. In addition, no -OH peak was observed at 3000 cm-1 , which provides
further evidence that cyclohexanol is not in our product (or is at negligible amounts).

Post-Lab Questions
6.33
No -OH frequency would be observed.
6.34
A C-H sp2 and a C=C frequency would be newly observed.
6.35
The higher ratio shows favoring of the formation of the more stable product, Compound 1. Compound 1
is more substituted than compound 2 and does not possess as many steric interactions. Thus it is more
stable and is favored.
6.36
-SR2+ is an excellent leaving group due to its nature as a weak base, especially with its positive charge. -
SH is a strong base and is thus not a good leaving group.
6.37
The Cl in HCl is a good nucleophile and will cause competing reactions between E1 and Sn1. The other
groups in the other acids will only favor the E1 reaction.