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Lab #9.
Notes:
<COMMON ERRORS>
• reversing assignments of protons in final 2
products:
electronegativity is only partially
responsible for shifts.
*SEE TABLE 8.4 in G&M pg.267 and text
following*
</COMMON ERRORS>
* Please write in a clear, well-organized manner.
CLASS
AVERAGES: Avg. technique - 36.3
Avg. total lab - 242.5
Avg. yield acetanilide
- 96
Avg. yield 4-Br-acetanilide
- 62 ± 7
Avg. yield 4-Br-2-Cl-acetanilide - 64 ± 8
Avg. yield 4-Br-2-Cl-aniline -
74 ± 11
Avg. yield 4-Br-2-Cl-6-I-aniline - 59 ± 8
Avg. yield 1-Br-3-Cl-5-I-benzene - 38 ± 13
Avg. OVERALL yield
- 7 ± 4
Rubric:
•60 - Technique ("average" is
7/12)
5 - skill & understanding (avg.3)
4 - preparation & efficiency (avg.2)
3 - safety (avg.2)
(per day)
12 - Acetylation & Bromination
12 - Chlorination
12 - Amide
hydrolysis
12 - Iodination
12 - Deamination
•120- Completed Report
15 -
Format
5 - proper citation, reference.
5 - grammar & proofing, typographical errors, style
5 - title, heading, neatness, legibility (where applicable)
15 - Abstract
I was very very picky! You all wrote some very nice ones.
5 - what: (SM-to-Prod rxn, type of synthesis[six-step])
5 - methodology (brief)
3 - theory (EAS, activation, protecting groups, directing groups)
2 - important results/conclusions/qualitative yield & purity, etc.
* - addit'l ±1 for form/typographical errors or exceptional writing.
60 -
Intro/Results/Discussion
30 - Introduction (intro, theory, etc)
8 - introductory text
22 - Reaction & Mechanisms
I was extremely picky regarding errors here.
4 - Protection
6 - Bromination, Chlorination, Iodination
4 - Hydrolysis
6 - Diazotization/Deamination
2 - redox rxns
(complete, correct, arrows, charge,
equilibria and major steps)
30 - Results & Discussion (side reactions, spectra, etc)
8 - side reactions
(Ar+->ArOH, Ar+->ArOEt, halide exchange, di-acetylation)
18 - discussion, errors, spectra etcetera
4 - conclusion/closure
30 -
Experimental
8 - OVERALL Yield (based on class yield average, avg.6/8),
`
22 - experimental, complete and correct.
•60 - Analysis of Spectra (IR & NMR), complete and
correct:
4 - IR
6 - NMR (Per
compound)
10 - acetanilide
10 -
4-Br-acetanilide
10 -
4-Br-2-Cl-acetanilide
10 -
4-Br-2-Cl-aniline
10 -
4-Br-2-Cl-6-I-aniline
10 -
1-Br-3-Cl-5-I-benzene
•60 - Samples (yield, purity, etc.):
5 - yield (based on class yield averages
statistics:
1/5: >> 1σ lower than avg,
2/5: < avg
3/5: ~ avg,
4/5: > avg,
5/5: > 1σ higher than avg)
5 - purity - based on MPs, crystal quality, color, etc.
(per compound)
10 - acetanilide
10 -
4-Br-acetanilide
10 -
4-Br-2-Cl-acetanilide
10 -
4-Br-2-Cl-aniline
10 -
4-Br-2-Cl-6-I-aniline
10 -
1-Br-3-Cl-5-I-benzene
*Well done!* Thanks once again for the honour of TAing you all.
You were awesome students and really showed a great deal of improvement this
semester. Good luck and stay safe next year and beyond!
CLASS
AVERAGES: 1260 ± 49
(81.3%)
