Haloalkanes. Chapter 8. Structure
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1 Haloalkanes Chapter 8 1 Structure Haloalkane (alkyl halide): A compound containing a halogen atom covalently bonded to an sp 3 hybridized carbon; given the symbol RX. Haloalkene (vinylic halide): A compound containing a halogen atom bonded to an sp 2 hybridized carbon. Haloarene (aryl halide): A compound containing a halogen atom bonded to a benzene ring; given the symbol ArX. We study these in Chapter 21. 2
2 Nomenclature 1. Number the parent chain to give the substituent encountered first the lowest number, whether it is halogen or an alkyl group. 2. Indicate halogen substituents by the prefixes fluoro-, chloro-, bromo-, and iodo- and list them in alphabetical order with other substituents. 3. Locate each halogen on the parent chain by giving it a number preceding the name of the halogen. 4. In haloalkenes, number the parent chain to give carbon atoms of the double bond the lower set of numbers. 3 Nomenclature examples Cl H trans-2-chlorocyclohexanol omo-4-meth ylpentane 4-omocyclohexen e Common names: name the alkyl group followed by the name of the halide. 2-omobutane (sec-butyl bromide) Cl Chloroethene (Vinyl chloride) Cl 3-Chloropropene (Allyl chloride) 4
3 Nomenclature Several polyhaloalkanes are common solvents and are generally referred to by their common or trivial names. CH 2 Cl 2 Dichloromethane (Methylene chloride) CHCl 3 Trichloromethane (Chloroform) CH 3 CCl 3 1,1,1-Trichloroethane (Methyl chloroform) CCl2 = CHCl Trichloroethylene (Trichlor) Hydrocarbons in which all hydrogens are replaced by halogens are commonly named as perhaloalkanes or perhaloalkenes. Cl Cl Cl C C Cl Cl Cl Perchloroeth ane F F F F C C C F F F F Perfluoropropane Cl Cl C C Cl Cl Perchloroethylene 5 Halothane: inhalational anesthetic (1950 s) Isoflurane: inhalational anesthetic Discovered in 1963; not released for Use in the US until
4 Van der Waals Forces Haloalkanes are associated in the liquid state by van der Waals forces. van der Waals forces: A group intermolecular attractive forces including: dipole-dipole forces. dipole-induced dipole forces. induced dipole-induced dipole (dispersion) forces. van der Waals forces pull molecules together. As molecules are brought closer and closer, van der Waals attractive forces are overcome by repulsive forces between electron clouds of adjacent atoms or molecules 7 Van der Waals Forces The energy minimum is where the attractive and repulsive forces are balanced. Nonbonded interatomic and intermolecular distances at these minima can be measured by x-ray crystallography and each atom and group of atoms can be assigned a van der Waals radius. Nonbonded atoms in a molecule cannot approach each other closer than the sum of their van der Waals radii without causing nonbonded interaction strain. H F Cl CH 2 CH 3 I Increasing van der Waals radius (pm) 8
5 9 Boiling Points For an alkane and a haloalkane of comparable size and shape, the haloalkane has the higher boiling point. The difference is due almost entirely to the greater polarizability of the three unshared pairs of electrons on halogen compared with the low polarizability of shared electron pairs of covalent bonds. CH 3 CH 3 CH 3 bp -89 C bp 4 C Polarizability: A measure of the ease of distortion of the distribution of electron density about an atom in response to interaction with other molecules and ions; fluorine has a very low polarizability, iodine has a very high polarizability. 10
6 Increasing Polarizability Polarizability: A measure of the ease of distortion of the distribution of electron density 11 Boiling Points Among constitutional isomers, branched isomers have a more compact shape, decreased area of contact, decreased van der Waals attractive forces between neighbors, and lower boiling points. 1-omob utane bp 100 C 2-omo-2-methylbutan e bp 72 C 12
7 Boiling points of fluoroalkanes are comparable to those of hydrocarbons of similar molecular weight and shape. CH 3 CHCH 3 2-Methylprop ane MW 58.1, bp -1 C Hexan e (MW 86.2, bp 69 C) Boiling Points CH 3 F CH 3 CHCH 3 2-Flu oroprop ane MW 62.1, bp -11 C The low boiling points of fluoroalkanes are the result of the small size of fluorine, the tightness with which its electrons are held, and their particularly low polarizability. F 1-Fluoropentan e (MW 90.1, bp 63 C) 13 Density The densities of liquid haloalkanes are greater than those of hydrocarbons of comparable molecular weight. A halogen has a greater mass per volume than a methyl or methylene group. All liquid bromoalkanes and iodoalkanes are more dense than water. Di- and polyhalogenated alkanes are more dense than water. Haloalkane CH 2 X 2 CHX 3 CX 4 D ens ity (g/ml) at 25 C X= Cl I
8 Bond Length & Strengths C-F bonds are stronger than C-H bonds; C-Cl, C- and C-I bonds are weaker. Bond C-F C-H C-Cl C- C-I Bond Length (pm) Bond Dissociation Ethalpy [kj (kcal)/mol] 464 (111) 414 (99) 355 (85) 309 (78) 228 (57) 15 Halogenation of Alkanes If a mixture of methane and chlorine is kept in the dark at room temperature, no change occurs. If the mixture is heated or exposed to visible or ultraviolet light, reaction begins at once with the evolution of heat. heat CH 4 Cl 2 CH 3 Cl HCl Methane Ch loromethan e (Methyl ch loride) H kj (23.9 kcal)/mol Substitution: A reaction in which an atom or group of atoms is replaced by another atom or group of atoms. 16
9 Halogenation of Alkanes If chloromethane is allowed to react with more chlorine, a mixture of chloromethanes is formed. heat CH 3 Cl Cl 2 CH 2 Cl 2 HCl Chloromethane (Methyl chlorid e) Dichloromethane (Methylene chloride) Cl 2 Cl CH 2 Cl 2 CHCl 2 3 CCl heat heat 4 Trichloromethane (Chloroform) Dichloromethane (Methylene chloride) Tetrachloromethane (Carbon tetrachloride) 17 Regioselectivity Regioselectivity is high for bromination, but chlorination is NT as selective CH 3 CH 2 CH 3 2 Prop ane heat or light CH 3 CHCH 3 2-omopropan e (92%) CH 3 CH 2 CH 2 1-omop ropan e (8%) H Cl CH 3 CH 2 CH 3 Cl heat 2 CH 3 CHCH 3 CH 3 CH 2 CH 2 Cl or light Propane 2-Ch loroprop ane 1-Chloropropane (57%) (43%) HCl 18
10 Energetics Bond Dissociation Enthalpies (BDE) Increasing Stability Hydrocarbon C 6 H 5 CH 2 -H (CH 3 ) 3 C-H (CH 3 ) 2 CH-H CH 3 CH 2 -H CH 3 -H CH 2 =CH-H Radical CH 2 =CHCH 2 -H CH 2 =CHCH 2 C 6 H 5 CH 2 (CH 3 ) 3 C (CH 3 ) 2 CH CH 3 CH 2 CH 3 CH 2 =CH Name of Radical Allyl Ben zyl t ert -Butyl Isopropyl Ethyl Meth yl Vinyl Type of Radical Allylic Ben zylic Meth yl Vinylic H 0 kj (kcal)/mol 372 (89) 376 (90) 405 (97) 414 (99) 421 (101) 439 (105) 464 (111) Increasing E 19 Mechanisms Radical: any chemical species that contains one or more unpaired electrons. Radicals are formed by homolytic bond cleavage. The order of stability of alkyl radicals is 3 > 2 > 1 > methyl. 20
11 Mechanisms The order of stability of alkyl radicals is 3 > 2 > 1 > methyl. Cl Cl Chlorine CH 3 CH 2 CH 2 CH 3 Diethyl peroxide light 80 Cl Cl H 0 = 247 kj/mol Chlorine atoms (59 kcal/mol) CH 3 CH 2 CH 2 CH 3 H 0 = 159 kj/mol Ethoxy radicals (38 kcal/mol) CH 3 CH 3 Ethane heat CH 3 CH 3 Methyl radicals H 0 = 376 kj/mol (90 kcal/mol) 21 Radical Chain Mechanism Chain initiation: A step in a chain reaction characterized by formation of reactive intermediates (radicals, anions, or cations) from nonradical or noncharged molecules. Step 1: light Cl Cl Cl Cl or heat 22
12 Radical Chain Mechanism Chain propagation: A step in a chain reaction characterized by the reaction of a reactive intermediate and a molecule to form a new radical or reactive intermediate and a new molecule. Step 2: CH 3 CH 2 H Cl CH 3 CH 2 H Cl Step 3: CH 3 CH 2 Cl Cl CH 3 CH 2 Chain length: The number of times the cycle of chain propagation steps repeats in a chain reaction. Cl Cl 23 Radical Chain Mechanism Chain termination: A step in a chain reaction that involves destruction of reactive intermediates. Step 4: CH 3 CH 2 CH 2 CH 3 CH 3 CH 2 -CH 2 CH 3 Step 5: CH 3 CH 2 Cl CH 3 CH 2 -Cl Step 6: Step 7: Cl Cl H CH 3 CH 2 CH 2 -CH 2 Cl Cl CH 3 CH 3 CH 2 =CH 2 24
13 Chain Propagation Steps For any set of chain propagation steps, their equations add to the observed stoichiometry. enthalpies add to the observed H 0. CH 3 CH 2 -H Cl CH 3 CH 2 H- Cl H 0, kj/mol (kcal/mol) -9 (-2) CH 3 CH 2 Cl-Cl CH 3 CH 2 -Cl Cl -108 (-26) CH 3 CH 2 -H Cl-Cl CH 3 CH 2 -Cl H- Cl -117 (-28) 25 Stereochemistry When radical halogenation produces a chiral center or takes place at a hydrogen on a chiral center, the product is a racemic mixture of R and S enantiomers. CH 3 CH 2 CH 2 CH 3 2 heat or light CH 3 CH 2 CHCH 3 H Butane (R,S)-2-omobutane (racemic) 26
14 Allylic carbon: A C atom adjacent to a C-C double bond. Allylic hydrogen: An H on an allylic carbon. 350 C CH 2 = CHCH 3 Cl 2 CH 2 = CHCH 2 Cl HCl Propene Allylic Halogenation 3-Chloropropene (Allyl chloride) an allylic C-H bond is weaker than a vinylic C-H bond. H H H H C 464 kj /mol C C 372 kj/mol H H 27 Allylic omination Allylic bromination using NBS: hν N CH 2 Cl 2 N H Cyclohexene 3-omocyclohexene N-omosuccinimide (NBS) Succinimide 28
15 Allylic omination A radical chain mechanism Chain initiation N hν N Chain propagation What happens to H? CH 2 =CHCH 2 -H CH 2 =CHCH 2 H- CH 2 =CHCH 2 - CH 2 =CHCH 2-29 NBS neutralizes H and the protonated amide then provides 2 for the chain process: Allylic omination Mechanism: N- H- N-H 2 30
16 Allylic omination chain termination - CH 2 = CHCH 2 CH 2 = CHCH 2 - CH 2 = CHCH 2 CH 2 CH= CH 2 CH 2 = CHCH 2 -CH 2 CH= CH 2 31 Radical Addn of H to Alkenes Addition of H to alkenes gives either Markovnikov addition or non-markovnikov addition depending on reaction conditions. Markovnikov addition occurs when radicals are absent. non-markovnikov addition occurs when peroxides or other sources of radicals are present. Mark ovnikov ad dition H no peroxid es 2-Methylpropene 2-omo-2- methylprop ane N on-markovn ikov addition H peroxides 2-Methylpropene 1-omo-2- methylp ropan e 32
17 Radical Addn of H to Alkenes Addition of HCl and HI gives only Markovnikov products. To account for the the non-markovnikov addition of H in the presence of peroxides, a radical chain mechanism is proposed-- Chain initiation: Step 1: R- -R R R A dialkyl peroxide Two alkoxy radicals Step 2: R H R H omine radical 33 Radical Addn of H to Alkenes Chain propagation: Step 3: A 3 radical Step 4: H H 1-omo-2- methylpropan e 34
18 Radical Addn of H to Alkenes Chain termination: Step 5: Step 6: 35 Radical Addn of H to Alkenes This pair of reactions illustrates how the products of a reaction can be changed by a change in experimental conditions: Polar addition of H is regioselective, with protonation of the alkene preceding the addition of - to the more substituted carbon. Radical addition of H is also regioselective, with atom adding to the less substituted carbon. 36
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