CHM 2230
Winter 2007
Experiment 8
Organic Chemistry II Laboratory
3028 or 3040 Science Hall
A Synthetic Competition Multi-step Synthesis
Purpose: In reality, there may be more than one way to prepare a product. The question is,
which method is best? Two m
onsbond to aken fr om Wikipedia.or g chargehas been substituents, commonly Substances of Very High Concern listor 'non-stabilised'. No ne (PAH), a carbon bearing a negative r mat ion t anthracene is not carcinogenic but and two recently included in the al
Exp. 5- The Aldol Condensation
Purpose:
To carry out two Aldol concentration reactions which no heat is needed
to obtain the condensation products. Two reactions differ in the number
of enolizable protons at the a-carbon
Precautions:
- Acetone, ethanol an
Exp. 2- Dehydration
Purpose:
In the dehydration of 2-methylcyclohexanol, two possible products are
possible the Zaitzev product ( more substituted alkene) and Hoffman
product (less substituted alkene)
Precautions:
- Keep all organic liquids in the hood as
Exp. 8- Amide Hydrolysis
Purpose:
To covert p-bromoacetanilide to p-bromoaniline under acidic conditions
Precautions:
- p-bromoaniline is an irritant
- Hydrochloric acid is corrosive, harmful if inhaled and can cause
burns
Reaction:
Procedure:
- p-bromoac
Test Canvas: EAS-Bromination CHM_2230_1509_.
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Test Canvas: Diastereoselectivity CHM_2230_1509_.
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Test Canvas: Dehydration of an Alcohol CHM_2230_1509_.
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Test Canvas: The Wittig Reaction CHM_2230_1509_.
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Exp. 7- A synthetic Competition (Multi-Step Synthesis)
Purpose:
To determine the most efficient synthetic pathway to make methyl mnitrobenzoate. In comparing the overall percent yield of the path, you
will be able to determine the best synthetic route. Ti
Exp. 3- A problem with Diastereoselectivity
Purpose:
To determine the stereo chemical outcome of the reduction of benzoin
by formation of an acetal
Precautions:
- Sodium borohydride is a reducing agent
- Concentrated sulfuric acid and hydrochloric acids a
Exp. 1- Bromination of acetanilide
Purpose:
To convert acetanilide to p-bromoacetanilide using in Situ generation of
bromide
Precautions:
- Ethanol is flammable
- Sodium Hypochlorite is and oxidizing agent and releases toxic
fumes
- Acetic acid is corrosi
Exp. 4- Stereospecific Witting Reaction
Purpose:
To convert 9-anthraldehyde to trans-9-(2-phenylethenyl) anthracene by
the addition of a stabilized phosphorous ylide.
Precautions:
- 9-anthraldehyde may be harmful if inhaled; work in the hood
- Ingestion o
CHM 2230
Organic Chemistry II Laboratory
Spring/Summer 2012
Dr. Ashley Campanali
Office: 101.3 Undergraduate Office Suite
Email: [email protected]
Phone: (313) 577-3589
Office Hours: Tuesday and Thursday 10:35-11:05 am (until the week of 6/25, Tuesd
O
O
H
H
N
acetanilide
CH3
N
CH3
add H2O
which makes
H3O+
HNO3
H2SO4
Mechanism:
similar mechanism
see section 15.11
on p. 706 of Bruice
and p. 637
NO2
in Bruice
This material is not
isolated. It is hydrolyzed.
Some ortho product is present.
Percent yield i
Exp. 1 Electrophilic Aromatic Substitution
Preparation and Separation of o- and p-Nitroaniline
Chapter 27, p 243 of Bell, Clark and Taber
Review the chapter on Electrophilic Aromatic Substitution in Bruice. Pay special attention to the
mechanism for nitra
CHM 2230
Exp. 1: Electrophilic Aromatic Substitution
Preparation and Separation of o- and p-Nitroaniline
Name of Student: _
Access ID: _
Day and time of lab section: _
Name of Laboratory TA: _
possible
Title
Date
Purpose
Table of Reagents (Include amounts
