Class Notes (808,088)
Canada (493,058)
Chemistry (588)
CHM247H1 (30)

chm247 all about Alkyl halide.pdf

13 Pages
Unlock Document

University of Toronto St. George
Cecilia Kutas

July 1112 2012 CHM247H1REVIEW Organic Alkyl Halides RX and ArX Where XF Cl Br IHALOGEN COMPOUNDS IN HUMAN PHYSIOLOGYTable salt is iodized to prevent goitreThyroxine IOHOIOHNH2IOIORGANO HALIDES FROM MARINE ORGANISMSAlmost 100 different organic halides have been isolated from edible red seaweed Asparagopsis taxiformis o A taxiformis grows on the edges of coral reefs in areas of constant water motionMANMADE ORGANO HALIDESHalothane an anaesthetic interacts with a serine tyrosine and carbonyl oxygen from a leucine FASEB Journal 2005 19567576Roderick Eckenhoff MD ClCl POLLUTION PROBLEMS AND ORGANO HALIDES HCCl Disposal of organo halides can cause many environmental issues 3 DDT dichlorodiphenyltrichloroethane is a nonspecific pesticide that kills insects that spread diseases exmalaria typhus o Weakly polar very stable organic molecule insoluble in water cannot be washed away o Persists in environment collects in fatty tissue humans accumulate it in the liver bioaccumulates o Interferes with the eggshell formation of eagles and hawksCHM247H1HALIDES ARE IMPORTANT INDUSTRIALLYPolymers o Vinyl chloride CHCHCl is polymerized to give PVC polyvinylchloride plastics 2ClClClClClClCl o Tetrafluoroethylene FCCFTeflon used for bulletproof vests and nonstick cookware 22 Refrigerants o ExFreon12 CFCl 22 Small molecules with no Hbonding low boiling points therefore they evaporate quickly and extract heatLinked to ozone depletionSolvents o ExChloroform CHCl 3 Very good nonpolar solventno HbondsPotential carcinogenALKYL VINYL and ARYL HALIDES looking at the hybridization of the C to which the X is bondedAll have different reactivity 3o CClan alkyl halide Cl is bonded to an sphybridized carbon 42o FCCFa vinyl halide F is bonded to an sphybridized carbon on an isolated double bond 22o CHBran aryl halide Br is bonded to an sp2hybridized carbon of an aromatic ring 65 Vinyl and aryl halides are similarALSO o Benzyl halide CHCHX 652Also similar o Allyl halide CHCHCHX 22 SPECTROSCOPY VeryIRthe CX bond stretch appears in deshielded Deshielded 1the fingerprint region 500800cm o Hard to identify via IR we Alkyl region dont look for halogen bond stretches 1 H NMRHCX o 2540 Would be complex multiplet splitting but it o H is deshielded by the is caused by similar Hs all attached to ClCs influence of the 3 neighbours on two different carbons but electronegative X so the in similar proton environmentssignal appears downfield Unlike the usual case the quartet andtriplet are NOT splitting each other PREPARATION OF ORGANIC HALIDES BrSeveral ways weve seen before 1 Halogenation of alkenes Br2 Hydrohalogenation of alkenesHBr R Markovnikov Br 2 ether CCl4 HBrBrBr ROOR hRRRantiMarkovnikov
More Less

Related notes for CHM247H1

Log In


Don't have an account?

Join OneClass

Access over 10 million pages of study
documents for 1.3 million courses.

Sign up

Join to view


By registering, I agree to the Terms and Privacy Policies
Already have an account?
Just a few more details

So we can recommend you notes for your school.

Reset Password

Please enter below the email address you registered with and we will send you a link to reset your password.

Add your courses

Get notes from the top students in your class.