Amides
BY:
Jacob Baird and Nathan Carrier
Structural components
-Carbonyl:
Carbon pi bonded to oxygen
https://upload.wikimedia.org/wikipedia/commons/4/46/IUPAC
_carbonyl_divalent_group.png
Structural components continued
- Nitrogen
- Bonded to carbonyl
- Two valence electrons for the free
radicals
Structural components continued
- Free Radical
- Any molecule or element with 1
free valence electron
General Structure
C- Is the base carbon
O- The double bonded oxygen
N- Is the nitrogen attached to the carbon
R- Represents the free radicals
https://upload.wikimedia.org/wikipedia/commons/2/2e/A
mide-general.png
Propanamide
3
2
1
Naming scheme
• [Positions][Attachments][Family name (subtract ‘e’)][-amide (suffix)]
• Ex: 2-methylpentanamide
(Although double bond present not
an
alkene)
Naming scheme continued
• Positions• According to the location of the parent chain starting at
carbonyl (1), or the nitrogen
• Attachments onto the nitrogen are said to be at position N
coming before all integers ( Not to be confused with “n”)
N,N- Dimethylbutanamide
3-methylpentanamide
http://chemsink.com:8080/examples/jsp/marvin/generate_
image.jsp?mol=CCCC(C)C(%3DO)N&format=png%3Aw40
0%2Ch200%2Cb32%2C%23ffffff
Parent chain and naming examples
http://www.sigmaaldrich.com/content/dam/sigmaaldrich/structure9/020/mfcd00008023.eps/_jcr_content/renditio
ns/mfcd00008023-medium.png
Give it a try
http://chemsink.com:8080/e
xamples/jsp/marvin/generat
e_image.jsp?mol=CCCNC(%
3DO)C(C(C)C)Br&format=p
ng:w400,h200,b32,#ffffff
Reaction properties
• Peptide bond- A peptide bond (sometimes mistakenly called
amino bond) is a covalent bond that is formed between two
molecules when the carboxyl group of one molecule reacts with
the amino group of the another molecule, releasing a molecule of
water. This is a a condensation reaction and usually occurs
between amino acids. The resulting CO-NH bond is called a
peptide bond, and the resulting molecule is an amide. Via peptide
guide.com
http://www.mhhe.com/biosci/genbio
/enger/student/olc/art_quizzes/genb
iomedia/0037.jpg
Synthesis of an amide
• The easiest way to make an amide is using carboxylic acids.
What the reaction is using ethanoic acid and ammonium
carbonate to create ammonium ethanoate, dehydrate that
and you have made an amide!
Nucleophilic Acyl Substitution
• Hydrolysis- Is the reaction using water to break the bond or
bonds of a molecule.
Everyday uses
• The most commonly used amide(#1)
has to be acetamide! Peptide bonds in
protein are necessary for life.
• The second most commonly used amide
would be acetaminophen which is found
in many pain relievers
1)https://cdn1.sph.harvard.edu/wp-content/uploads/sites/30/2012/09/Protein.jpg
2)http://dailymed.nlm.nih.gov/dailymed/archives/image.cfm?archiveid=150463&type=i
mg&name=hydrocodone-bitartrate-and-acetaminophen-tablet-2.jpg
Everyday uses continued
• Formamide is used as a cryoprotectant and a gel stabilizer.
Cryoprotectant is a protectant for biological tissue from
freezing damage. That due to ice formation. Draw :
Everyday uses continued
• Phenylamide is a highly active class of fungicide specifically
controlling plant pathogens of the Downy Mildews.
https://upload.wikimedia.org/wikipedia/commons/thumb/0/0c
/Benzamide.svg/170px-Benzamide.svg.png
Hopefully not everyday use
Lysergic acid diethylamide or commonly
known as LSD.
Polyamides
• Are polymers in which a carboxylic acid molecules and a lone amine are
bonded together by amide bonds creating various types of useful substances
like nylon. This is known as a condensation polymer.
Inorganic amides
Is an amide without the organic
carbonyl compound, so the inorganic
amide is just a cation attached to
NH2. Not nearly as large or as
important as the organic amide
however.
http://cdn.meme.am/instances/61290566.jpg
Reference Pictures
•
•
https://upload.wikimedia.org/wikipedia/commons/2/2e/Amide-general.png
•
http://chemsink.com:8080/examples/jsp/marvin/generate_image.jsp?mol=CCCC(C)C(%3DO)N&format=png%3Aw400%2Ch200%2Cb32
%2C%23ffffff
•
http://www.sigmaaldrich.com/content/dam/sigma-aldrich/structure9/020/mfcd00008023.eps/_jcr_content/renditions/mfcd00008023medium.png
•
•
•
•
•
http://www.mhhe.com/biosci/genbio/enger/student/olc/art_quizzes/genbiomedia/0037.jpg
http://chemsink.com:8080/examples/jsp/marvin/generate_image.jsp?mol=CCCNC(%3DO)C(C(C)C)Br&format=png%3Aw400%2Ch200
%2Cb32%2C%23ffffff https://upload.wikimedia.org/wikipedia/commons/4/46/IUPAC_carbonyl_divalent_group.png
http://cdn.meme.am/instances/61290566.jpg
https://cdn1.sph.harvard.edu/wp-content/uploads/sites/30/2012/09/Protein.jpg
https://upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Benzamide.svg/170px-Benzamide.svg.png
http://dailymed.nlm.nih.gov/dailymed/archives/image.cfm?archiveid=150463&type=img&name=hydrocodone-bitartrate-andacetaminophen-tablet-2.jpg
References
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http://science.jrank.org/pages/285/Amides.html
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch20reactionsamides.html
Chemguide.co.uk
Chem.ucalgary.ca
Ucdavis.chemwiki
Dub.unl.edu
Pubchem.com
Sigmaaldrich.com
F.R.A.C.ca
Textbook resources:
Organic chemistry- Joseph M.Hornback