In alkylamines, N is bonded to a C that is sp3 hybridized.
Nitrogen is also sp3 hybridized. Like carbon, it has a pyramidal shape:
The lone pair of electrons is involved in reactions.
Amines act as bases or nucleophiles, d
Robertson CHEZ] 1 Organic Chemisny [1 Laboratory Spring 2015
Organic Chemistry II (CHE 211-71)
Laboratory Quiz 2
Name: Date: (www 3) 2015
Please analyze the following 1H, 13C NMR and IR spectra to determine the structure
of an unknown organic compound
Purpose: To synthesize the following modified nucleoside utilizing a Suzuki coupling reaction for
the site-specific incorporation into a short strand of DNA.
Preparation of Amides
Amides are the most stable carboxylic acid derivatives.
Nitrogen is less electronegative than oxygen.
The nitrogen attached to the carbonyl carbon can donate its lone pair of electrons to
stabilize the carbonyl.
The hydrogen att
Reactions of aldehydes and ketones
-Reactions of alpha hydrogens ( hydrogens)
hydrogens are attached to the
hydrogens are reactive.
C C C C
Which hydrogen is the alpha hydrogen? In ketones and aldehydes the functional group is the carbonyl
In the presence of an oxidizing agent, aldehydes can be oxidized to form carboxylic acids. In the
above reaction, an aldehyde is being oxidized to give a carboxylic acid. A ketone wont be
Reactions of -hydrogens, continued
Either acidic or
either acidic or
In the -h
Preparation of Amines
There are four ways to prepare amines:
1. Alkylation of ammonia
2. Reduction with LAH
a. From amides
b. From nitriles
c. From nitro compounds
d. From alkyl azide
e. From aldehydes or ketones
3. Ring opening of epoxides
Aldol Condensation Part 2
In order to participate in an aldol condensation reaction, the aldehyde or ketone should have
an -proton that can be removed by a base. This is called an enolizable aldehyde ketone.
If there is no -proton, this is a non-enolizabl
Reactions of Amides
1. Reduction with LAH
1. Reduction with LAH
Amides can be reduced to give amines. This requires a strong reducing agent, such as LAH.
LAH is a strong reducing agent
Aldol condensation is a reaction of an enol and an enolate. It is called an aldol because it forms
an intermediate -hydroxy aldehyde product which is both an aldehyde and an alcohol, so
aldol. The enolate undergoes nucleophlic addition
Nitrogen-containing compounds are known as alkaloids. Amines are the strongest uncharged
bases found in significant quantities in physiological conditions.
Aliphatic amines have N attached to a carbon that is sp3 hybridized:
Identification of Organic Compounds Using IR and 1H-NMR Spectroscopy
The following infrared and proton NMR spectra provide a good introduction to the use of these techniques
for identifying organic compounds and their structures. The top spectra are IR an