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)