CHEM1201 Lecture Notes

Monday, 12 August 2013 DDT First synthesied in 1874. Its insecticidal properties werent discovered to the 80s, was originally used to control Malaria. In terms of restricting the number of malaria carrying mosquitos, is good, but it has a profound number of running consequence. These have toxic side eects. It was banned in 1972. The eects upon the rerpduction in birds by applying DDT to the environment, there were so few birds around giving rise to the silent spring. Its still used in some counties. Other Interesting and Important Compounds Containing halogens Fluorouracil is the analogue to uracil, which is used in cancer tratment. Halothan (anasthetic). Dicult to administer the right amounts, it tends to stick around in fatty tissue because its a realtively nonpolar compound. Even thhough the individual bonds themselves are very polar, the oerall molecules themselves are very lipophillic, or hydrophobic. So its hard to get the amount of anaesthetic right. So the reason for this is because this compond,w hen people inhale it, it nds its way into fatty tissue, and when they move around more, it gets released, etc. Its not a perfect structure. Chlorouorocarbons, known as freons, originally used as regrigerant. They are long lived compounds and have been demonstrated to lead to chemical reactions which deplete the ozone layer.

Amines
We have sp3 hydbridied tetrahedral geometry on the nitrogen atom. We esentially have a pyramidal shape. Structure and properties The presence of N means that we get hydrogen bonding between molecules of primary amines, and so dimethyl ehter and dimethylamine, despite having about the same molecular, have very dierent BPs. 1

 Acid-Base Reactions Higher pKa of conjugate acid (ammonium salt) means more basic the base (amine). There is something curious about aniline, P hN H2 is quite a low pKa, 4.6, because theres a big dierence between this and triethylamine, ethyline, ammonia, which have pKa between 10.75 and 9.2. This is because there is conjugation with the aromatic ring. Generally, the longer the carbon chain, the less water soluble it becomes. You can turn it around by reacting this with a relatively mild acid, and because they are ionic, they become very soluble in water. Amines tend to be smelly compounds once their volatile. But when theyre produced into salts, theyre not AMines as Nucleophiles Amines have that lone pair to form new Nitrogen bonds. Theyll do it with a proton, but theyll also do it with electrophiles. You can go from primary to secondary amines, etc. You are performing a substitution reaction to form a new N-C bond, followed by an acid-base reaction to form that higher amine. It turns out that primary amines, when you react it with an alkyl halide, you create. Primary amines are less sterically hindered, whereas secondary amines are more sterically hindered. But we know that carbon subsitutients are electron donating. This makes secondary more reactive that primary, even though it may not necessarily be deduced from the steric considerations. Nicotine Produced naturally by many plants. Produced by the roots, but it ends up in the leaves. Its extremely widely used, and every cigarette releases 1mg. The lethal dose is 30mg. So the therapeutic index for this one is pretty bad. If you tried to market a medicine with a similar therapeutic index is bad. Ampetamine derivatives Methamphetamine is the secondary amine. Methamphetamine, crystal meth, are the hydrochloride salt of the substance, The free base version is a volatile liquid. These are oil, fatty substance, volatile substance. 2

 Both enantiomers are biologically active. Generally on the street you get the racemic, and sometimes the single enantiomers, and the single enantiomier is what people hardered to the drug will want. Production and distribution of these substances is controlled by authorities. It is sometimes used in the clinic, but the bad side eects, means its restricted. Phenethylamine is found in chocolate. There was a theory in 80s that peoples craving for chcolate is because of this. But this is false, since it gets destroyed by enzymes into a carboxyic acid and doesnt ahve the biolgocial properties that MDMA and speed do. 25I-NBOme. Closely related to the other compounds. This is starting to replace LSD Crack Cocaine Coaine is the ammonium chloride salt, this is the stu that is extracted from the plant. But crack cocaine is a chrystalline solid. They have very dierent properties. MP: Cocaine = 195, Crack = 95. Thus people smoke crack. Its a similar reaction to if you take sh and add citric acid.

Carbonyl Group Chemistry

Aldehydes and Ketones These are compounds containing a carbonyl group, C = O. formaldehyde is the simplest molecule in this class. All four atomes lie on one plane. So in a ketone, you have 3 carbons and an oxygen in the same plane, but in an aldehyde, youd have two carbones, an oxygen and Hydrogen. All the bond angles are approximately 120 degrees. Functional groups containing a carbonyl absorb at around 1700cm Structure and Bonding We have a pi bond, sp2 hybridised. If you have an aldehyde,you end with -al Ketones end with -one Nomenclature Oxidation Levels of Functional Groups

 Odiation of Aldehydes Aldehyles get oxidised to carboxylic acids because when theyre exposed to dchromate ion get it. We also saw that secondary alcohols get oxidised to ketones, but they dont get a reactions. This is because you cant break carbon-carbon bonds.