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Purpose: demonstrate that tertiary alcohols favor a substitution over elimination reaction when paired with a haloacid
Purpose: demonstrate that tertiary alcohols favor a substitution over elimination reaction when paired with a haloacid
Learning Objectives
Learning Objectives
Observe liquid-liquid interface of two immiscible liquids and perform extraction
Use gas chromatography (GC) to determine percent composition of products
Apply IR Spectroscopy to determine reaction success
Interpret chemical test results to determine presence or absence of alkyl halide
t-Pentanol, ball and stick 3D model
Substitution Mechanism!
t-Pentyl chloride, ball and stick 3D model
Make the reaction happen...
Make the reaction happen...
Reaction Set-up
Reaction Set-up
Alcohol (0.80 - 1.20 mL)
2.50 mL HCl conc.
Calculate theoretical yield
Reaction Work-up
Reaction Work-up
Wash w/ water
Quench w/ weak base
Wash w/ water again
Product Yield
Product Yield
Transfer to vial
'weigh' in remote lab = subtract product loss from theoretical yield
Analyze - make sure you have what you think you have!
Analyze - make sure you have what you think you have!
t-pentanol is a clear liquid, so is t-pentyl chloride :/
Use several forms of analysis to confirm the reaction happened.
Silver Nitrate Test
alkyl halide present?
Sodium Iodide Test
alkyl halide present?
GC Analysis
% composition
IR Analysis
Functional groups?
Assessment components - to-do list
Assessment components - to-do list
Exp 6 Pre-lab quiz - take on Canvas before section
Fill out the Partner Agreement & Data / Observations from Canvas during lab
Every student submits this individually on Canvas at the end of lab
Participation during your enrolled section - tracked by Zoom polls - contact your TA immediately if you are unable to attend and we'll make other arrangements
Review the Academic Integrity Form on Canvas
Contribute to the Experiment 6 Canvas Discussion
You and your partner complete the lab report (abstract, notebook pages, & in-lab question) together per your Partner Agreement
Full details on page 2 of the Exp 6 PDF
Submit on GradeScope as a pair one week - due Sun 12/13, 11:59pm
Neatness & Organization - proper format, spelling, and grammar. Refer to writing guidelines, Parts A-B.
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