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Copy of Organic Chemistry - Amines
Transcript of Copy of Organic Chemistry - Amines
aminoethane Secondary Amines two alkyl groups replacing two hydrogens from the ammonia molecule Ex. CH3 –- N –- CH3
N- methylaminomethane By: Eulah S. & Yezarni W. Tertiary Amines three alkyl groups replacing all three hydrogens from the ammonia molecule Ex. CH3 –- N –- CH3
N,N-dimethylaminomethane Physical Properties of Amines 1. High Melting and Boiling Points M.P and B.P increase as molar mass of the amine compound increases The polar N-H bonds between amine molecules form HYDROGEN BONDS Comparing Amines to Alkanes 1-aminopropane Propane
Melting Point: 190K Melting Point: 83K
Boiling Point: 321K Boiling Point: 231K 2. Solubility in Water amines are soluble in water; H-bonds form between hydrogen atoms of amines and oxygen atoms of water water is a polar solvent, and can dissolve amines, which are polar solutes nitrogen atom with a lone pair of electrons 3. Odour amines have an odour comparable to ammonia; fishy smell or smell of decay 4. Shape of Functional Group amines have a triangular pyramidal shape due to its three bonding electron pairs and its lone pair of electrons Reactions of Preparation 1. Preparing amines from halogenoalkanes Halogenoalkanes are alkane groups containing one or more halogens ex. Bromine When halogenoalkane is added to ammonia, an amine compound is produced 2. Preparing amines
from nitriles Nitriles are molecules containing the -CN group Reduction (gaining electrons) of nitriles can prepare amines A reducing agent, such as LiAIH4, is used Hydrogen bonds also exists between nitrogen atoms of amines and hydrogen atoms of water (in primary amines) 3. Preparing amines from amides Amides (organic compounds with carbonyl functional group) can be reduced to produce amines LiAlH4 can be used as a reducing agent Uses of Amines 1. Amino Acids in nature, important amines act as amino acids amino acids are vital to the body since they form proteins Proteins provide structure, function and regulation of the body’s organs and tissues 2. Dyes aromatic amines are used in dye production amines react with nitric (III) acid to produce salt The salts undergo reactions to produce a coloured azo-compound Methyl orange is used as a pH indicator Sunset yellow FCF is used in orange Jello 3. Drugs and Medication a) Chlorpheniramine inhibits immune response to relieve allergies from colds, itchy skin, insect bites, etc. b) Ephedrine and Pseudoephedrine amine drugs that are used for allergies involving respiration (decongestants) c)Chlorpromazine a tranquilizing drug used to relieve anxiety and sometimes mental disorders Chemical Properties and Reactions 1. Basicity Amines are bases because they have an electron pair that accepts protons The lone pairs on
the nitrogen atom gives amines basic properties 2. Reactions with Acid similar to NH3 base reacting with acids a hydrogen ion bonds to the lone pair of the nitrogen atom; an ammonium ion is produced 3. Reaction with Water acid-base reaction N R
| R - |
R : H-O |
H creating N |
R R - R
| : H + O - H - 4. Hofmann elimination amine -> quaternary ammoinium iodide -> tertiary amine + alkane +Ag2O +H20 +heat +methyl
iodide amine -> quaternary ammoinium iodide -> tertiary amine + alkane Hofmann rearrangement
(hofman degradation) primary amide -> primary amine -1carbon +NaOH CH3CONH2 + Br2 + 4NaOH -> CH3NH2 + Na2CO3 + 2NaBr + 2H2O IUPAC naming 1. Primary Amines a. determine carbon chain it is attached to
b. determine the number of the carbon that the
amine is attached to 2. Secondary Amines +Br2 a. determine longest continuous carbon chain
b. recognize smaller chain of carbons substituting an H in NH2 use the prefix "N-alkyl group"
c. resultant name is:
N-alkyle group-# of carbon NH is attached to-amino(carbonchain) 3. Tertiary Amines a. recognize longest continuous carbon chain
b. recognize the alkyls substituting the H bonds in nitrogen
c. Resultant name will be:
N-sm alkyl group-N-lg alkyl group-# of carbon N is attached to-amino(carbonchain) If two alkyl groups replacing both hydrogens of NH2 are the same, the name would be "N, N-di(carbonchain)" *2+ amine groups attached a. recognize carbon chain
b. use prefixes di, tri, etc. to name the number of amines
*di[amino(carbonchain)] or tri[amino(carbonchain)]
c. determine the carbon number each amine group is on ` H H H
| | |
H - C - N - C - C - H
| | | |
H | H H
H CH3 - CH2 - N - CH2 - CH3
CH3 H - C - C - N - C - C - C - H H - C - C - C - C - H NH2CH2CH2CH2CH2NH2 H H H H H
| | | | | | | | | | | H H H H H H H H H H
| | | | | | | |
H N H H / \
H H 1,4-diaminobutane Review Questions! What is the difference between primary, secondary and tertiary amines? The number of alkyl groups replacing hydrogens from the ammonia molecule Why do amines exhibit relatively high melting and boiling points? Strong N-H hydrogen bonds that form between amine compounds What is the molecular shape of the amine functional group? Triangular Pyramid What are the three uses of amine compounds? 1. Amino Acids
3. Drugs and Medications THANK YOU! Naming and Drawing Amines Name 12. on the handout! Name 14. on the handout! Name 16. on the handout! Draw 2-methyl-3aminopentane!