9 sept 2019 · o Common names; alkyl halides are derived by naming the alkyl group followed by the halide Nomenclature of Haloalkanes and Haloarenes
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Haloalkanes contain halogen atom(s) attached to the name haloalkanes and haloarenes derived by naming the alkyl group followed by the halide
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Haloalkanes and Haloarenes Classification and Nomenclature Classification • Based on number of halogen atoms • Monohalogen • Dihalogen
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9 sept 2019 · o Common names; alkyl halides are derived by naming the alkyl group followed by the halide Nomenclature of Haloalkanes and Haloarenes
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BrCH2 CH2CN BrCH = CHCN isobut lene sodium t-buto ide t-but l meth l ether EVALUATION PAPER - HALOGEN DERIVATIVES OF ALKANES AND ARENES
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Prof. Mohamed El-Newehy
Chemistry Department, College of Science, King Saud UniversityCHEM 241
Organic Chemistry II
FOR CHEMISTRY' STUDENTS, COLLEGE OF SCIENCE
PRE-REQUISITES COURSE; CHEM 240
CREDIT HOURS; 2 (2+0)1
Organo-halogen CompoundsBased on NCERTOn the basis of number of halogen atoms; Haloalkanesandhaloarenesmay be classified as follows:
Classification of Haloalkanes and Haloarenesmono,di,orpolyhalogen(tri-,tetra-, etc.) compoundsdepending on whether they contain one, two or more halogen atoms in
their structures.Monohalocompoundsmay further be classified according to the hybridization of the carbon atom to which the halogen is
bonded, as following:The replacement of hydrogen atom(s) in a hydrocarbon, aliphatic or aromatic, by halogen atom(s) (X=F,Cl,Br,orI;
fluoro, chloro, bromo, and iodo compounds) results in the formation of alkyl halide (haloalkane) and aryl halide
(haloarene) (a)Alkyl halides or haloalkanes(R - X) oThe halogen atom is bonded to an alkyl group (R) & thegeneral formulaisC n H 2n+1 X. (b)Allylic halides oThe halogen atom is bonded to ansp 3 -hybridized carbon atom next to carbon-carbon double bond (C=C).Compounds Containing sp
3C - X Bond (X= F, Cl, Br, I)
Classification of Haloalkanes and Haloarenes
(c)Benzylic halides oThe halogen atom is bonded to ansp 3 -hybridized carbon atom next to an aromatic ring.oThey are classified asprimary,secondaryortertiaryaccording to the nature of carbon to which halogen is attached.
(a)Vinylic halides oThese are the compounds in which the halogen atom is bonded to ansp 2 -hybridized carbon atom of a carbon-carbon double bond (C = C). (b)Aryl halides oThese are the compounds in which the halogen atom is bonded to thesp 2 -hybridized carbon atom of an aromatic ring.Compounds Containing sp
2C - X Bond (X= F, Cl, Br, I)
p &OClassification of Haloalkanes and Haloarenes
oCommon names;alkyl halides are derived by naming the alkyl group followed by the halide.Alkyl halide
oIUPAC system;alkyl halides are named ashalosubstituted hydrocarbons.Haloalkanes
Nomenclature of Haloalkanes and Haloarenes
Haloarenes
oHaloarenes are the common as well as IUPAC names ofaryl halides.oFor dihalogen derivatives, the prefixeso-,m-,p- are used in common system but in IUPAC system, the numerals
1,2; 1,3 and 1,4 are used.
%U &O+Nature of C-X Bond C-X Bond
oSince halogen atoms are more electronegative than carbon, thecarbon-halogen bond of alkyl halide is polarized;
thecarbon atom bears a partial positive chargewhereas thehalogen atom bears a partial negative charge.
Dipole moment
(kJ/mol)Bond Length (Å)Bond1.8474521.39CH
3 -F1.8603511.78CH
3 -Cl1.8302931.93CH
3 -Br1.6362342.14CH
3 -ICarbon-Halogen (C - X) Bond Lengths, Bond Strength and Dipole MomentsImportance of Organohalogen Compounds
a) Solvents:Alkyl halides are used as solventsfor relatively non-polar compounds: CCl 4 , CHCl 3 , CCl 3 CH 3 , CH 2 Cl 2 , ....etc. b) Reagents: Alkyl halides are used as the starting materialsfor the synthesis of many compounds.Alkyl halides are used in nucleophilic reactions, elimination reactions, formation of organometallics, and etc.
c) Refrigerants:Freons (ChloroFluoroCarbon) d) Pesticides:DDT, Aldrin, Chlordane) Herbicides: Kills broad leaf weeds but allow narrow leaf plants to grow unharmed and in greater yield
2,4-D2,4-dichlorophenoxyacetic acidThey are good solvents for fats and oils.
Polychloro compounds, such as trichloroethylene and tetrachloroethylene, are widely used as solvents for dry cleaning.
f) Chlorine containing antibiotic, chloramphenicol: is very effective for the treatment of typhoid fever.
g) Our body produces iodine containing hormone, thyroxine: the deficiency of which causes a disease called goiter.
IodideBromideChlorideFlourideGroup
Density (g mL
-1 )bp (°C)Density (g mL -1 )bp (°C)Density (g mL -1 )bp (°C)Density (g mL -1 )bp (°C) 2.28 2042.51.73
03.60.92
20 -23.80.84 -60 -78.4Methyl 1.95 20721.46
2038.40.91
1513.10.72
20 -37.7Ethyl 1.74 201021.35
2070.80.89
2046.60.78
-3 -2.5Propyl 1.61 201301.27
201010.89
2078.40.78
2032Butyl
2.04 20561.52
14160.91
20 -13.90.68 26-72CH 2 =CH- 1.84 22
102-1031.40
20700.94
2045-3CH
2 =CHCH 2 1.82 201891.52
201551.10
201321.02
20 85C6 H 5 1.73 25
93
10 1.44 22
2011.10
251791.02
25140C
6 H 5 CH 2 The simplemonofluoroandmonochlorocompounds areless dense than water, Themonobromoandmonoiododerivatives have densitiesgreater than water. As the number of halogen atoms increases, the density increases.
Density
All organic halidesare insoluble in water.
All organic halidesare soluble in common organic solvents (benzene, ether, etc.).Solubility
Physical Properties of Organic Halides
Boiling points
Within a series of halides, the boiling points increase with increasing molecular weights. This is due to the increase in van der Waals forces when the size and mass of the halogen atom increases. Within a homologous series, the boiling points also increase regularly with molecular weights. Withinaseriesofisomers, the straight-chain compound has the highest boiling point, and the most branched isomer the lowest boiling point. Haloalkanes generally have a boiling point that is higher than the alkane they are derived from due to - The increased molecular weight due to the large halogen atoms - The increased intermolecular forces due to the polar bonds, and the increasing polarizabilty of the halogen.Physical Properties of Organic Halides
Preparation of Halogen Compounds
Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes,