Chemistry 318                 Organic Chemistry Lab II                  Fall 2019

This syllabus can be found at http://mason.gmu.edu/~sslayden/Lab/index.html

Important additional course information is found on the CHEM 318 section of BlackBoard.

Lab Text: J. R. Mohrig, D. G. Alberg, G. E. Hofmeister, P. F. Schatz, and C. N. Hammond, Laboratory Techniques in Organic Chemistry, 4th edition (2014).

Lab Manual: S. W. Slayden, R. J. Roth, and W. M. Stalick, Laboratory Manual: Organic Chemistry 315, 318 (2017).

Lecture Text: T. W. G. Solomons, C. B. Fryhle, and S. A. Snyder, Organic Chemistry, 12th edition (2016).

Videos: Most viewing assignments can be found at
https://ocw.mit.edu/resources/res-5-0001-digital-lab-techniques-manual-spring-2007/videos
(MIT OpenCourseWare Creative Commons license).

CHEM 314 lecture is a pre- or co-requisite for CHEM 318 lab. If you previously took CHEM 314, you must have earned at least a C to use it as a pre-requisite for Chem 318. If you drop or withdraw from CHEM 314, you must also drop/withdraw from CHEM 318.

Add, drop, and selective withdrawal deadlines can be found at http://registrar.gmu.edu.

It is the responsibility of all students to be familiar with and adhere to the GMU Honor Code.

If you are a student with a disability and you need academic accommodations, please contact Disability Services at 993-2474, http://ds.gmu.edu. All academic accommodations must be arranged through Disability Services.


Course Schedule

Date

Experiment Title

Reading Assignment

Report Due

 Lab 1

Aug 26-30

Introduction and safety; check-in; NMR video

Lab Manual 1-20

Mohrig ch 1 (omit 1.6, 1.7)

 

 Lab 2

Sep 3-9

Nuclear magnetic resonance spectroscopy (1H- and 13C-NMR)

 

Lab Manual 91

Mohrig ch 22 (except 22.1-22.3, 22.8, 22.10, pp. 382-391); 23.1-23.2

NMR PowerPoint tutorial on Bb

 

 Lab 3

Sep 10-16

Bromination of toluene; review IR; NMR continued.

Lab Manual 93-100, 49-58

Mohrig 22.11, 21.1-21.5, 21.7-21.11

Solomons Sec. 15.1-15.3

IR PowerPoint tutorial on Bb

IR sample prep video

 

 Lab 4

Sep 17-23

Nitration of methyl benzoate

Lab Manual 103-106

Mohrig 3.2, 15.2, 15.3, 15.5, 15.8, 9.4, 9.6

Solomons Sec. 15.8-15.9

Recrystallization video (9:51-14:33 min)

Bromination of Toluene
Report Form
- Bromination of Toluene (do not use the one from the Manual) [Slightly revised 9/15/19]

 Lab 5

Sep 24-30

Synthesis of 4,4'-di-tert-butylbiphenyl; nitration of methyl benzoate continued

Lab Manual 107-111

Mohrig 7.1, 10.3-10.5, 10.7, 11.1-11.3

Solomons 15.6A, C

M.Pt. video; Reflux video (0-4:30 min)

Nitration of methyl benzoate: Separation Scheme

 Lab 6

Oct 1-7

Identification of an unknown, part 1

Lab Manual 113-114; 45-47; 49-51

Mohrig [12.3-12.3a, 12.8], [13.3-13.4]

Distillation video (0-8:41 min)

Nitration of methyl benzoate: remainder of report

 Lab 7

Oct 8-15

Identification of an unknown, part 2; GMU NMR Center (PH 18)
Monday classes do not meet on Mon. Oct. 14.

Monday classes MEET on Tues. Oct. 15

Mohrig 22.1, 22.2 (pp. 353-355)

NMR document

Synthesis of 4,4'-di-tert-butylbiphenyl

 Lab 8

Oct 16-22

Grignard reaction -Synthesis of benzoic acid, part 1

Experimental Procedure (not in Manual

Solomons 12.6B, 12.7B, 12.8B, 17.3(6.)

Identification of Unknown

 Lab 9

Oct 23-29

Isolation and recrystallization of benzoic acid, part 2

Experimental Procedure (not in Manual)

Mohrig 10.2

Extraction video (0-11:25, 14:30-16:40 min)

 

 Lab 10

Oct 30-Nov 5

Qualitative & spectroscopic analysis of aldehydes and ketones

Lab Manual 119-125

Solomons 16.11, 16.13, 16.14

Grignard Reaction

 Lab 11

Nov 6-12

Synthesis of banana oil

Lab Manual 127-130

Mohrig 7.1, 10.3-10.5, 10.7, 11.1-11.3
Solomons 17.7A

Qualitative Analysis of Aldehydes/Ketones

 Lab 12

Nov 13-19

Synthesis of dibenzalacetone

Lab Manual 131-132

Procedure: TLC of dibenzalacetone (not in Manual)

Mohrig 18.6, 18.8, 18.9, 15.2, 15.3, 15.5, 15.8, 9.4, 9.6

Synthesis of banana oil

 Lab 13

Nov 20-26

Synthesis of biodiesel

Lab Manual 133-137

Mohrig pp. 74-75

Synthesis of dibenzalacetone

 Lab 14

Dec 2-6

Final exam (Location TBA)

Synthesis of biodiesel