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Purpose: To determine the major product in the acid-catalyzed dehydration of methycyclohexanols using GC analysis, demonstrating Zaitsev's rule.
Purpose: To determine the major product in the acid-catalyzed dehydration of methycyclohexanols using GC analysis, demonstrating Zaitsev's rule.
Analysis of products
Analysis of products
- % yield
- Permanganate (KMnO4) test for alkenes
- IR
- GC
Zaitsev's Rule
Zaitsev's Rule
More highly substituted alkenes are more stable
Substitution patterns are determined by the number of carbon atoms (highlighted in green) directly attached to the alkene C's
Many, many elimination reactions were carried out with a small base, each consistently favoring the more highly substituted alkene.
Klein, Organic Chemistry, 3rd ed. Figure 7.13
Learning Objectives
Learning Objectives
Observe microscale distillation apparatus to collect products of a dehydration reaction
Use gas chromatography (GC) to determine percent composition of products, exemplifying Zaitsev’s rule
Apply IR Spectroscopy to determine reaction success
Interpret permanganate tests to determine presence or absence of alkene
Recommended Background Reading on Organic Reactions
Recommended Background Reading on Organic Reactions
Chapter Sections in McMurry, Organic Chemistry, 8th ed. or Klein, Organic Chemistry, 3rd ed.
Elimination Reactions: McMurry 11.7-11.10 or Klein 7.1, 7.6 – 7.7, 7.9, 7.11
Dehydration of Alcohols: McMurry 17.6 or Klein - 12.9
Oxidative Cleavage of Alkenes: McMurry - 7.9 Klein - 8.12, Klein text doesn’t specifically cover oxidative cleavage with KMnO4
Assessment Components - Checklist
Assessment Components - Checklist
Exp 5 Pre-lab quiz - take on Canvas before lab
Prepare your notebook per the Exp 5 Lab Notebook Templates on Canvas
After 'performing' this remote lab and gathering data, upload your Exp 5 Lab Notebook pages to Canvas
Complete the Exp 5 Lab Report (abstract and in-lab questions) per instructions on the last page of the Exp 5 document
You have the OPTION to work on this lab with ONE partner and submit the lab report to GradeScope together
one student uploads, select "add Group Member" - MAX group of TWO
It is 100% OK to complete this report individually
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