Amides BY: Jacob Baird and Nathan Carrier. Structural components - Carbonyl: Carbon pi bonded to...

AmidesBY:

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 carbonO- The double bonded oxygenN- Is the nitrogen attached to the carbonR- Represents the free radicals

https://upload.wikimedia.org/wikipedia/commons/2/2e/Amide-general.png

Propanamide

12

3

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%3Aw400%2Ch200%2Cb32%2C%23ffffff

Parent chain and naming examples

http://www.sigmaaldrich.com/content/dam/sigma-aldrich/structure9/020/mfcd00008023.eps/_jcr_content/renditions/mfcd00008023-medium.png

Give it a try

http://chemsink.com:8080/examples/jsp/marvin/generate_image.jsp?mol=CCCNC(%3DO)C(C(C)C)Br&format=png: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/genbiomedia/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

2)http://dailymed.nlm.nih.gov/dailymed/archives/image.cfm?archiveid=150463&type=img&name=hydrocodone-bitartrate-and-acetaminophen-tablet-2.jpg

1)https://cdn1.sph.harvard.edu/wp-content/uploads/sites/30/2012/09/Protein.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=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://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/mfcd00008023-medium.png

• http://www.mhhe.com/biosci/genbio/enger/student/olc/art_quizzes/genbiomedia/0037.jpg

• 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-and-acetaminophen-tablet-2.jpg

References

• 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