Chemistry 318 Organic Chemistry Lab II Spring 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

Week 1

Jan 22-28

Introduction and safety; check-in; NMR video

Lab Manual 1-20

Mohrig ch 1 (omit 1.6, 1.7)

 

Week 2


Jan 29-Feb 4

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

Videos: C-NMR https://www.youtube.com/watch?v=RfsqdgXxS8s; https://www.youtube.com/watch?v=hAJQjZIE6x0;

H-NMR: https://www.khanacademy.org/science/organic-chemistry/spectroscopy-jay/proton-nmr/v/introduction-to-proton-nmr

 

Lab Manual 91

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

PowerPoint tutorial on Bb

 

Week 3


Feb 5-11

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

PowerPoint tutorial on Bb

IR sample prep video

 

Week 4


Feb 12-18

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

Week 5


Feb 19-25

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

Week 6


Feb 26-Mar 4

Identification of an unknown, part 1

(Spring Break Mar 1115: no classes)

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

Week 7


Mar 5-18

Identification of an unknown, part 2; GMU NMR Center (PH 18)

Mohrig 22.1, 22.2 (pp. 353-355)

NMR document

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

Week 8


Mar 19-25

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

Week 9


Mar 26-Apr 1

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)

 

Week 10


Apr 2-8

Qualitative & spectroscopic analysis of aldehydes and ketones

Lab Manual 119-125

Solomons 16.11, 16.13, 16.14

Grignard Reaction

Week 11


Apr 9-15

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

Week 12


Apr 16-22

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

Week 13


Apr 23-29

Synthesis of biodiesel

Lab Manual 133-137

Mohrig pp. 74-75

Synthesis of dibenzalacetone

Week 14


Apr 30-May 6

Final exam (Location TBA)

Synthesis of biodiesel