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Organic Chemistry Project: Amide

Organic Chemistry Project: Amide. Parisa Jallali Kendal Smith Lindsey Veazie Alyssa Hunt. Basic Structure. Structure: amides have an amino-carbonyl function attached to an alkyl or aromatic group. What is an amide?.

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Organic Chemistry Project: Amide

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  1. Organic Chemistry Project: Amide Parisa Jallali Kendal Smith Lindsey Veazie Alyssa Hunt

  2. Basic Structure • Structure: amides have an amino-carbonyl function attached to an alkyl or aromatic group

  3. What is an amide? It is “an organic compound containing the group -C(O)NH2, related to ammonia by replacing a hydrogen atom by an acyl group.”

  4. Characteristics of Amides • They’re derived from carboxylic acids • Contains the –CONH2 group • The most commonly discussed amides: CH3CONH2 • 3 simplest amides: HCONH2 – methanamide, CH3CH2CONH2 – propanamide, CH3CONH2 – ethanamide

  5. Characteristics continued... • Smallest amides soluble in water because they can hydrogen bond in water. • Amide = the most common non-basic function group • Contain oxygen • Occur widely in living organisms • “Amides are the fusion of an acyl group, and the remnant of deprotonating of NH3, whereas amines are the fusion of an alkyl or aryl group to the same chemical.”

  6. Characteristics continued… • The way to write an amide is: R(CO)NH2 or CH3-C=O-NH3 or CH3CONH3 or RCONH3 • The amide has a C=O double bond next to the Nitrogen

  7. Amides – Nomenclature Naming Rules start with the carboxylic acid Take out the –ic or the –ioc acid suffix Tag on the –amide suffix Examples Methanoic acid methanamide Ethanoic acid ethanamide Acetic acid acetamide Butanoic acid butanamide

  8. Mechanism Definition • Mechanism: sequence of steps which occurs during a chemical reaction

  9. Mechanisms • Hoffman Rearrangement: starts off with an amide, a strong base and a halogen. The strong base ionizes the amide to make an amide anion.

  10. Mechanisms Continued • Amide Reduction: Lithium aluminum hydride follows carbonyl substitution-addition to reduce an amide to an amine.

  11. Mechanisms Continued • Amide Dehydration: amides are converted to nitriles with dehydrating reagents

  12. Examples of Amides The amide that results from the acetic acid is acetamide, it becomes ethanamide using the IUPAC name If there was a methyl group and an ethyl group attached to the nitrogen = N-ethyl-N-methylacetamide Results from butyric acid is butyramide with IUPAC = butanamide

  13. Examples continued… 4) Two methyl groups attached to the nitrogen = N, N-dimethylacetamide 5) N-methylethanamide

  14. Real World Example: Valium • Diazepam (Valium) is a benzodiazepene tranquilizer • It works by enhancing the inhibitory neurotransmitter, GABA • It binds to the same protein as ethanol, making possible combinations of valium and ethanol deadly

  15. Structure

  16. Uses • Diazepam is used to relieve muscle spasms, anxiety, and seizures and can also help control agitation caused by alcohol withdrawals

  17. Statistics • Valium Abuse, according to the National Institute of Health, impacts all Americans, because we all pay the cost for it. • Valium Abuse cost Americans over $484 billion annually. This figure includes healthcare costs (and abuses of that system), lost job wages, traffic accidents, crime and the associated criminal justice system costs.

  18. Question #1 1) What are amides derived from? A) carboxylic acid B) Aldehyde C) Amine D) Ketone Answer: A) Carboxylic Acid

  19. Question #2 2) True or False… The Amide is the most common non-basic functional group Answer: True

  20. Question #3 3) Smallest amides are soluble in water because… They can carbon bond They can nitrogen bond They can hydrogen bond They can oxygen bond Answer: C) They can hydrogen bond

  21. Question #4 4) The amide contains _______ atoms and is connected to _______. oxygen and carbon hydrogen and oxygen nitrogen and carbon carbon and nitrogen Answer: C) nitrogen and carbon

  22. Question #5 • 5) Using the nomenclature rules, which of the following would be the way to name acetic acid? a) acetamide acid b) acetamine c) acetamide d) aceticamide Answer: c) acetamide

  23. Work Cited http://www.differencebetween.net/science/difference-between-amine-and-amide/ http://orgochem.wordpress.com/2009/06/05/amide-vs-amine/ http://www.google.com/#hl=en&q=amide&tbs=dfn:1&tbo=u&sa=X&ei=vwKoT82fFZKe8QSZpcC9Aw&ved=0CGgQkQ4&bav=on.2,or.r_gc.r_pw.r_qf.,cf.osb&fp=2ec9ddfdc67565f5&biw=1024&bih=408 www.chemicalforums.com/index.php?topic=47276.0 masterorganicchemistry.com/.../dehydration-of-amides-to-give-nitriles/ http://www.drug-addiction-support.org/Valium-Abuse-Facts.html http://www.chemguide.co.uk/organicprops/amidemenu.html http://books.google.com/books?id=FMuLzpHEhCwC&pg=PA547&lpg=PA547&dq=characteristics+of+amides&source=bl&ots=yEm7wS4MHM&sig=6tA86PKP-J8QYGKDz5_f_SdTxnc&hl=en&sa=X&ei=2c-nT6yaCJSW8gSUzcW1Aw&ved=0CFoQ6AEwAw#v=onepage&q=characteristics%20of%20amides&f=false

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