CH 362/CH 362H Lecture
Course Overview &
Acid Syntheses (“H” and “P”)
Jan. 5/6, 2016
CH 362/362H: Course Information
● Course Website
● Canvas is only used for recording scores and for electronic communication
● Safety
● Course assignments and grading (see course website for syllabus and detailed lecture/lab schedule)
Report 1: Communication – individual
Report 2: Full paper – groups
Report 3: Short paper – individual
Peer Review of Report 1
Oral Presentation (Week 10)
Notebook pages, weekly
Prelabs, weekly, total of 8
Lab performance
Project 1 Overview: “Strain Energy of the Cyclopropane Ring from Heats of Combustion”
Ring strain determined by:
• bomb calorimetry (experimental)
• semi-empirical quantum mechanical method (computational)
Overview of methyl cyclohexanecarboxylate synthesis (“H-ester”)
“H-acid” “H-ester”
Purify by vacuum distillation Characterize by IR and bp/pressure range
Purify by vacuum distillation Characterize by IR, GC bp/pressure range, and refractometry
Synthesis of cyclohexanecarboxylic acid (“H-acid”)
Grignard reagent
Grignard reagent
Synthesis of cyclohexanecarboxylic acid (“H-acid”)
Grignard reagent
Notes of Caution:
● Glassware must be dry
● handle chlorocyclohexane with care
● Grignard reagent cannulation is instructor-assisted
Stopping point on Thurs/Fri
Synthesis of cyclohexanecarboxylic acid (“H-acid”)
** Use caution! **
Aqueous work-up (Week 2 lecture)
Vacuum distill (Week 2 lecture)
Characterize by IR (Week 4 lecture)
Synthesize H-ester (Week 3 lecture)
Hydrolysis of carboxylate salt: (to be performed Tue/Wed of Week 2)
Synthesis of cyclohexanecarboxylic acid (“H-acid”)
Overview of butyl cyclopropanecarboxylate synthesis (“P-ester”)
“P-acid” “P-ester”
Purify by vacuum distillation Characterize by IR and bp/pressure range
Purify by vacuum distillation Characterize by IR, GC bp/pressure range, and refractometry
Synthesis of cyclopropanecarboxylic acid (“P-acid”)
Synthesis of cyclopropanecarboxylic acid (“P-acid”)
Synthesis of cyclopropanecarboxylic acid (“P-acid”)
Synthesis of cyclopropanecarboxylic acid (“P-acid”)
Notes of Caution:
● Glassware must be dry
● handle g-chlorobutyronitrile with care
● NaOH is caustic – use dust mask when transferring
● reaction is very exothermic
Stopping point on Thurs/Fri
Synthesis of cyclopropanecarboxylic acid (“P-acid”)
Hydrolysis of nitrile: (to be performed Tue/Wed of Week 2)
Acidification of sodium cyclopropanecarboxylate: (to be performed Tue/Wed or Thurs/Fri of Week 2)
** Use caution! **
Aqueous work-up (Week 2 lecture)
Vacuum distill (Week 2 lecture)
Characterize by IR (Week 4 lecture)
Synthesize H-ester (Week 3 lecture)