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S  0ݒ ``  X*  0 `   Z*  0 `   Z*z  bA޽h @ ?Parchment ̙33 Default Design 0 zr@ ( )   0෕ P    P*    0ؼ     R*  d  c $ ?    0̯  @  RClick to edit Master text styles Second level Third level Fourth level Fifth level!     S  6О `P   P*    6d `   R*  H  0޽h ? ̙3380___PPT10. 0X(   $+ X X 0Ǖ P    X*  X 0Lʕ     Z*  X 6Ε `P   X*  X 6 ӕ `   Z* H X 0޽h ? ̙3380___PPT10.1 0L0 P+(    0 3AN INTRODUCTION TO THE CHEMISTRY OF HALOGENOALKANESf!(282 f0f *f<fJ  C "A KTRE: . " <̙? x @ 0 0 ( <̙? x @L 0 0 ) 0x x m OKNOCKHARDY PUBLISHING(2 f * 0H%"`>B 2008 SPECIFICATIONS>G$G   B  s *޽h ? ̙33y___PPT10Y+D=' = @B +j  0L0  ` (  S  00Pa INTRODUCTION This Powerpoint show is one of several produced to help students understand selected topics at AS and A2 level Chemistry. It is based on the requirements of the AQA and OCR specifications but is suitable for other examination boards. Individual students may use the material at home for revision purposes or it may be used for classroom teaching if an interactive white board is available. Accompanying notes on this, and the full range of AS and A2 topics, are available from the KNOCKHARDY SCIENCE WEBSITE at... www.knockhardy.org.uk/sci.htm Navigation is achieved by... either clicking on the grey arrows at the foot of each page or using the left and right arrow keys on the keyboard (2 2(2 2  75, dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0dB   <D?( (    0X{0P( OKNOCKHARDY PUBLISHING(2    0hXx Z THE CHEMISTRY OF HALOGENOALKANES!(2!fB  s *޽h ? ̙33 0L0 "  p (  |  0  0 CONTENTS Structure of halogenoalkanes Physical properties of halogenoalkanes Nucleophilic substitution - theory Nucleophilic substitution - examples Substitution v. Elimination Elimination reactions Uses of haloalkanes CFC s Revision check listf 2"02 2b'  Y dB  <D)P0Q  0Pp@ 0 0dB  @ <D)PXP   0X0@ 0 0  0{m( @  0 0  6~mW!@  0 0  6p]3@  0 0  6Km@  0 0  6> ]x @  0 0  6 e@ @  0 0  6 ]8 m @<  0 0  0X \ THE CHEMISTRY OF HALOGENOALKANES !(2!f  6 ]8 @  0 0  6 m @8  0 0B  s *޽h ? ̙33y___PPT10Y+D=' = @B +L 0L0 z(  V  0H  pBefore you start it would be helpful to& Recall the definition of a covalent bond Be able to balance simple equations Be able to write out structures for hydrocarbons and their derivatives Understand the different types of bond fission Recall the chemical properties of alkanes, alkenes and alcohols H*(2 2)dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0ȖX \ THE CHEMISTRY OF HALOGENOALKANES !(2!fB  s *޽h ? ̙33 0L0  P((  PdB P <D)P0Q P 0Pp@ 0 0dB P@ <D)PXP P 0X0@ 0 0 P 0q~ kSTRUCTURE OF HALOGENOALKANES2(2ff  P 0G3 X0P Format Contain the functional group C-X where X is a halogen (F,Cl,Br or I) Halogenoalkanes - halogen is attached to an aliphatic skeleton - alkyl group Haloarenes - halogen is attached directly to a benzene (aromatic) ring @RP@Z#D )ZD    F   D B P s *޽h ? ̙33-  0L0  L[(  LdB L <D)P0Q L 0Pp@ 0 0dB L@ <D)PXP L 0X0@ 0 0 L 0L Gq~ kSTRUCTURE OF HALOGENOALKANES2(2ff  L 0G3 X0+  5gFormat Contain the functional group C-X where X is a halogen (F,Cl,Br or I) Halogenoalkanes - halogen is attached to an aliphatic skeleton - alkyl group Haloarenes - halogen is attached directly to a benzene (aromatic) ring Structural difference Halogenoalkanes are classified according to the environment of the halogen 6@RP@ Za@#F /JtD    F   ^  C /  L 02G O  ; PRIMARY 1 SECONDARY 2 TERTIARY 3x< 2 3 33T  L C ,A123chlorgW B L s *޽h ? ̙33J  0L0    tx (  tdB t <D)P0Q t 0Pp@ 0 0dB t@ <D)PXP t 0X0@ 0 0 t 0?Gq~ kSTRUCTURE OF HALOGENOALKANES2(2ff  t 0EG3 X0T R\Format Contain the functional group C-X where X is a halogen (F,Cl,Br or I) Halogenoalkanes - halogen is attached to an aliphatic skeleton - alkyl group Haloarenes - halogen is attached directly to a benzene (aromatic) ring Structural difference Halogenoalkanes are classified according to the environment of the halogen Names Based on original alkane with a prefix indicating halogens and position. CH3CH2CH2Cl 1-chloropropane CH3CHClCH3 2-chloropropane CH2ClCHClCH3 1,2-dichloropropane CH3CBr(CH3)CH3 2-bromo-2-methylpropaneD@RP@ Za@@XP#F .J HD    F   ^  _   /  t 0vG O  ; PRIMARY 1 SECONDARY 2 TERTIARY 3x< 2 3 33T  t C ,A123chlorgW B t s *޽h ? ̙33 0L0 h` h(  hT h C ,AbutchlorgdB h <D)P0Q h 0Pp@ 0 0dB h@ <D)PXP h 0X0@ 0 0 h 0Gqh~ u'STRUCTURAL ISOMERISM IN HALOGENOALKANES2((2'ffQ  h 0G0P qDifferent structures are possible due to... Different positions for the halogen and branching of the carbon chainP,XxF+F r  h 0GZ  X2-chlorobutane   h 0Ga 5 b2-chloro-2-methylpropane   h 0GT } X1-chlorobutane   h 0tGa 5 b1-chloro-2-methylpropane  B h s *޽h ? ̙33  0L0 C ;   (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0Gq~ aPHYSICAL PROPERTIES2(2ff   0G 0 PBoiling point Increases with molecular size due to increased van der Waals forces Mr bp / C chloroethane 64.5 13 1- chloropropane 78.5 47 1-bromopropane 124 71 Boiling point also increases for  straight chain isomers. Greater branching = lower inter-molecular forces bp / C 1-bromobutane CH3CH2CH2CH2Br 101 2-bromobutane CH3CH2CHBrCH3 91 2-bromo -2-methylpropane (CH3)3CBr 73 Solubility Halogenoalkanes are soluble in organic solvents but insoluble in waterl@ePxu@Px_@D333o3=533333333 333333 33333333 SF                8 B  s *޽h ? ̙33  0L0    X= (  XdB X <D)P0Q X 0Pp@ 0 0dB X@ <D)PXP X 0X0@ 0 0 X 0Gq~ gNUCLEOPHILIC SUBSTITUTION2(2ffH X 0,G X0 Theory " halogens have a greater electronegativity than carbon " electronegativity is the ability to attract the shared pair in a covalent bond " a dipole is induced in the C-X bond and it becomes polar " the carbon is thus open to attack by nucleophiles " nucleophile means  liking positive the greater electronegativity of the halogen attracts the shared pair of electrons so it becomes slightly negative; the bond is now polar. @V53"          )  u R  X C *A rxpolarghndB  X <DԔEB X s *޽h ? ̙33 0L0 A9 ( ( w (dB ( <D)P0Q ( 0Pp@ 0 0dB (@ <D)PXP ( 0X0@ 0 0 ( 0Gq~ gNUCLEOPHILIC SUBSTITUTION2(2ffF  ( 0 X0  Theory " halogens have a greater electronegativity than carbon " electronegativity is the ability to attract the shared pair in a covalent bond " a dipole is induced in the C-X bond and it becomes polar " the carbon is thus open to attack by nucleophiles " nucleophile means  liking positive the greater electronegativity of the halogen attracts the shared pair of electrons so it becomes slightly negative; the bond is now polar. NUCLEOPHILES " ELECTRON PAIR DONORS " possess at least one LONE PAIR of electrons " don t have to possess a negative charge " are attracted to the slightly positive (electron deficient) carbon " examples are OH, CN, NH3 and H2O (water is a poor nucleophile)d@V53    "          )      R  ( C *A nphilesg2 :  ( 0 % HOH CN NH3 H2ObI@5    I R  ( C *A rxpolarghndB  ( <DԔEB ( s *޽h ? ̙33 0L0   `-(  `dB ` <D)P0Q ` 0Pp@ 0 0dB `@ <D)PXP ` 0X0@ 0 0 ` 00qH8~ %NUCLEOPHILIC SUBSTITUTION - MECHANISMD&(2f f ` 06 SK- & the nucleophile uses its lone pair to provide the electrons for a new bond the halogen is displaced - carbon can only have 8 electrons in its outer shell the result is substitution following attack by a nucleophile the mechanism is therefore known as - NUCLEOPHILIC SUBSTITUTION@PF  *@      D R  ` C *A basicnsgDB ` s *޽h ? ̙33  0L0    <E (  <dB < <D)P0Q < 0Pp@ 0 0dB <@ <D)PXP < 0X0@ 0 0 < 0JqH8~ %NUCLEOPHILIC SUBSTITUTION - MECHANISMD&(2f f   < 0+ SK-  the nucleophile uses its lone pair to provide the electrons for a new bond the halogen is displaced - carbon can only have 8 electrons in its outer shell the result is substitution following attack by a nucleophile the mechanism is therefore known as - NUCLEOPHILIC SUBSTITUTION*@@      D   < 0X  ,Points the nucleophile has a lone pair of electrons the carbon-halogen bond is polar a  curly arrow is drawn from the lone pair to the slightly positive carbon atom a  curly arrow is used to show the movement of a pair of electrons carbon is restricted to 8 electrons in its outer shell - a bond must be broken the polar carbon-halogen bond breaks heterolytically (unevenly) the second  curly arrow shows the shared pair moving onto the halogen the halogen now has its own electron back plus that from the carbon atom it now becomes a negatively charged halide ion a halide ion (the leaving group) is displacedo@-!"R!EP!AH!J0!.@    M   R  < C *A basicnsgDB < s *޽h ? ̙33 0L0 " (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0pqH8~ %NUCLEOPHILIC SUBSTITUTION - MECHANISMD&(2f f   0Pu SK-  the nucleophile uses its lone pair to provide the electrons for a new bond the halogen is displaced - carbon can only have 8 electrons in its outer shell the result is substitution following attack by a nucleophile the mechanism is therefore known as - NUCLEOPHILIC SUBSTITUTION*@@      D R   C *A basicnsgD   0   #ANIMATION SHOWING THE SN2 MECHANISML$H   $ B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  &(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0qH8~ %NUCLEOPHILIC SUBSTITUTION - MECHANISMD&(2f f   0 SK-  the nucleophile uses its lone pair to provide the electrons for a new bond the halogen is displaced - carbon can only have 8 electrons in its outer shell the result is substitution following attack by a nucleophile the mechanism is therefore known as - NUCLEOPHILIC SUBSTITUTION*@@      D R  C *A basicnsgD   0ԝ   #ANIMATION SHOWING THE SN2 MECHANISML$H   $ f   C >A&SN2animtransparent Q]B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  @(  @dB @ <D)P0Q @ 0Pp@ 0 0dB @@ <D)PXP @ 0X0@ 0 0 @ 0q~ ,NUCLEOPHILIC SUBSTITUTION - RATE OF REACTIOND-(2f.  @ 0 0 &Basics An important reaction step is the breaking of the carbon-halogen (C-X) bond The rate of reaction depends on the strength of the C-X bond C-I 238 kJmol-1 weakest - easiest to break C-Br 276 kJmol-1 C-Cl 338 kJmol-1 C-F 484 kJmol-1 strongest - hardest to break ^S@>@5P0@1@ K<3 !   !&  C B @ s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 0d*( \ ddB d <D)P0Q d 0Pp@ 0 0dB d@ <D)PXP d 0X0@ 0 0 d 0q~ ,NUCLEOPHILIC SUBSTITUTION - RATE OF REACTIOND-(2f^ d 0 0  rBasics An important reaction step is the breaking of the carbon-halogen (C-X) bond The rate of reaction depends on the strength of the C-X bond C-I 238 kJmol-1 weakest - easiest to break C-Br 276 kJmol-1 C-Cl 338 kJmol-1 C-F 484 kJmol-1 strongest - hardest to break Experiment Water is a poor nucleophile but it can slowly displace halide ions C2H5Br(l) + H2O(l)   > C2H5OH(l) + H+ (aq) + Br(aq) If aqueous silver nitrate is shaken with a halogenoalkane (they are immiscible) the displaced halide combines with a silver ion to form a precipitate of a silver halide. The weaker the C-X bond the quicker the precipitate appears. S@>@5P0@1@@ K<0B3333333333 3333  e   k    /   p d 0 0  Ag+ (aq) + X(aq)   > AgX(s) AgCl white ppt AgBr cream ppt AgI yellow ppt6a'39                       B d s *޽h ? ̙33 0L0 :2@h(  hdB h <D)P0Q h 0Pp@ 0 0dB h@ <D)PXP h 0X0@ 0 0 h 0\q~ ,NUCLEOPHILIC SUBSTITUTION - RATE OF REACTIOND-(2f| h 0 0  Basics An important reaction step is the breaking of the carbon-halogen (C-X) bond The rate of reaction depends on the strength of the C-X bond C-I 238 kJmol-1 weakest - easiest to break C-Br 276 kJmol-1 C-Cl 338 kJmol-1 C-F 484 kJmol-1 strongest - hardest to break Experiment Water is a poor nucleophile but it can slowly displace halide ions C2H5Br(l) + H2O(l)   > C2H5OH(l) + H+ (aq) + Br(aq) If aqueous silver nitrate is shaken with a halogenoalkane (they are immiscible) the displaced halide combines with a silver ion to form a precipitate of a silver halide. The weaker the C-X bond the quicker the precipitate appears. Advanced This form of nucleophilic substitution is known as SN2; it is a bimolecular process. work An alternative method involves the initial breaking of the C-X bond to form a carbocation, or carbonium ion, (a unimolecular process - SN1 mechanism), which is then attacked by the nucleophile. SN1 is favoured for tertiary haloalkanes where there is steric hindrance to the attack and a more stable tertiary, 3, carbocation intermediate is formed.S@>@5P0@1@@ K<0S !4!!<^  e   k    /               ;        ;    B h s *޽h ? ̙33  0L0    $- ( w $dB $ <D)P0Q $ 0Pp@ 0 0dB $@ <D)PXP $ 0X0@ 0 0  $ 0pd1P FAQUEOUS SODIUM HYDROXIDE Reagent Aqueous* sodium (or potassium) hydroxide Conditions Reflux in aqueous solution (SOLVENT IS IMPORTANT) Product Alcohol Nucleophile hydroxide ion (OH) Equation e.g. C2H5Br(l) + NaOH(aq)   > C2H5OH(l) + NaBr(aq) Mechanism * WARNING It is important to quote the solvent when answering questions. Elimination takes place when ethanol is the solvent - SEE LATER The reaction (and the one with water) is known as HYDROLYSISH @P@3  3  6  33333 33333 3 I3K Z   ?       $ 0q~ gNUCLEOPHILIC SUBSTITUTION2(2ffP  $ C (A nsOHeth!p? B $ s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0 #` p(  pdB p <D)P0Q p 0Pp@ 0 0dB p@ <D)PXP p 0X0@ 0 02 p 01P< ,AQUEOUS SODIUM HYDROXIDE ANIMATED MECHANISMvH@H3  -  p 0H]q~ gNUCLEOPHILIC SUBSTITUTION2(2ffP  p C (AHOnsagRg)( B p s *޽h ? ̙33___PPT10e.+D=' = @B +  0L0    + ( w  dB   <D)P0Q   0Pp@ 0 0dB  @ <D)PXP   0X0@ 0 0   04a B@     0 1PN  2POTASSIUM CYANIDE Reagent Aqueous, alcoholic potassium (or sodium) cyanide Conditions Reflux in aqueous , alcoholic solution Product Nitrile (cyanide) Nucleophile cyanide ion (CN) Equation e.g. C2H5Br + KCN (aq/alc)   > C2H5CN + KBr(aq) Mechanism H@   ( 3333 33333 t      @        0@q~ gNUCLEOPHILIC SUBSTITUTION2(2ffP   C (Anscneth) B   s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0   P lm (  ldB l <D)P0Q l 0Pp@ 0 0dB l@ <D)PXP l 0X0@ 0 0 l 0ڄa B@  < l 01P POTASSIUM CYANIDE Reagent Aqueous, alcoholic potassium (or sodium) cyanide Conditions Reflux in aqueous , alcoholic solution Product Nitrile (cyanide) Nucleophile cyanide ion (CN) Equation e.g. C2H5Br + KCN (aq/alc)   > C2H5CN + KBr(aq) Mechanism Importance extends the carbon chain by one carbon atom the CN group can be converted to carboxylic acids or amines. Hydrolysis C2H5CN + 2H2O    > C2H5COOH + NH3 Reduction C2H5CN + 4[H]    > C2H5CH2NH2*H@   ( 3333 33333  k  t      @      l 0݄q~ gNUCLEOPHILIC SUBSTITUTION2(2ffP  l C (Anscneth) B l s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 p t8(  tdB t <D)P0Q t 0Pp@ 0 0dB t@ <D)PXP t 0X0@ 0 0 t 0 a B@   t 0%1P< %POTASSIUM CYANIDE ANIMATED MECHANISMRH@H  &  t 0-q~ gNUCLEOPHILIC SUBSTITUTION2(2ffP  t C (ACNnsagR2N( B t s *޽h ? ̙33y___PPT10Y+D=' = @B +H 0L0 W O 0  ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0<q~ gNUCLEOPHILIC SUBSTITUTION2(2ffd   0I1P  AMMONIA Reagent Aqueous, alcoholic ammonia (in EXCESS) Conditions Reflux in aqueous , alcoholic solution under pressure Product Amine Nucleophile Ammonia (NH3) Equation e.g. C2H5Br + 2NH3 (aq / alc)   > C2H5NH2 + NH4Br (i) C2H5Br + NH3 (aq / alc)   > C2H5NH2 + HBr (ii) HBr + NH3 (aq / alc)   > NH4Br Mechanism Notes The equation shows two ammonia molecules. The second one ensures that a salt is not formed..H,@5Pxt@   3 7   3333 33333333 33333333 33333333 3333333*4   8    ;               R   C *Ansnh3ethv X B  s *޽h ? ̙33y___PPT10Y+D=' = @B +c 0L0 @ 4(  4dB 4 <D)P0Q 4 0Pp@ 0 0dB 4@ <D)PXP 4 0X0@ 0 0 4 0vq~ gNUCLEOPHILIC SUBSTITUTION2(2ffb  4 0D1P  AMMONIA Why excess ammonia? The second ammonia molecule ensures the removal of HBr which would lead to the formation of a salt. A large excess ammonia ensures that further substitution doesn t take place - see below Problem Amines are also nucleophiles (lone pair on N) and can attack another molecule of halogenoalkane to produce a 2 amine. This too is a nucleophile and can react further producing a 3 amine and, eventually an ionic quarternary ammonium salt. C2H5NH2 + C2H5Br   > HBr + (C2H5)2NH diethylamine, a 2 amine (C2H5)2NH + C2H5Br   > HBr + (C2H5)3N triethylamine, a 3 amine (C2H5)3N + C2H5Br   > (C2H5)4N+ Br tetraethylammonium bromide a quaternary (4) salt  H@PF@ 33333333333333333#333333 33333333333'333333 3333 333333333F P     5  '   F   0     .     J  ' B 4 s *޽h ? ̙33 0L0 [SP 8(  8dB 8 <D)P0Q 8 0Pp@ 0 0dB 8@ <D)PXP 8 0X0@ 0 0 8 0ϊq~ gNUCLEOPHILIC SUBSTITUTION2(2ff  8 0Պ1P b~WATER Details A similar reaction to that with OH takes place with water. It is slower as water is a poor nucleophile. Equation C2H5Br(l) + H2O(l)   > C2H5OH(l) + HBr(aq) H@ D% 3333 3333333@o   =   B 8 s *޽h ? ̙33 0L0 80`D(  DdB D <D)P0Q D 0Pp@ 0 0dB D@ <D)PXP D 0X0@ 0 0 D 0q~ iELIMINATION v. SUBSTITUTION2(2ff  D 0l~0 SThe products of reactions between haloalkanes and OH are influenced by the solvent THT&"   '  8  ` D0p  D 6  ISOLVENT&(2  D 6\ >  hROLE OF OH 6 (2    D 6>  K MECHANISM& (2  D 6   IPRODUCT&(2 D 6,  GWATER&(2 D T??>  C NUCLEOPHILE (2  D T??>   D SUBSTITUTION (2  D T??  ?ALCOHOL(2 D 6\! ` IALCOHOL&(2 D T#?? > ` <BASE(2 D T)??> ` C ELIMINATION (2  D T-?? ` >ALKENE(2 D 02# 0Modes of attack Aqueous soln OH attacks the slightly positive carbon bonded to the halogen. OH acts as a nucleophile Alcoholic soln OH attacks one of the hydrogen atoms on a carbon atom adjacent the carbon bonded to the halogen. OH acts as a base (A BASE IS A PROTON ACCEPTOR) Both reactions take place at the same time but by varying the solvent you can influence which mechanism dominates. @2M@@P<@ Bg'xZ  Q      B D s *޽h ? ̙33e  0L0   p  ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  08Kq~ Y ELIMINATION2 (2 ff   0O0T bReagent Alcoholic sodium (or potassium) hydroxide Conditions Reflux in alcoholic solution Product Alkene Mechanism Elimination Equation C3H7Br + NaOH(alc)   > C3H6 + H2O + NaBr Mechanism the OH ion acts as a base and picks up a proton the proton comes from a carbon atom next to that bonded to the halogen the electron pair left moves to form a second bond between the carbon atoms the halogen is displaced overall there is ELIMINATION of HBr. Complication With unsymmetrical halogenoalkanes, you can get mixture of products2@ 3     3333 3 333333 3      d  .      )  " P   C (AelimOHg( B  s *޽h ? ̙33 0L0  x5(  xdB x <D)P0Q x 0Pp@ 0 0dB x@ <D)PXP x 0X0@ 0 0 x 0L,q~ Y ELIMINATION2 (2 ff x 0Q \ANIMATED MECHANISMH  P  x C (AElimagR( B x s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 \T 0(  0dB 0 <D)P0Q 0 0Pp@ 0 0dB 0@ <D)PXP 0 0X0@ 0 0 0 0q~ Y ELIMINATION2 (2 ffP  0 0i FComplication The OH removes a proton from a carbon atom adjacent the C bearing the halogen. If there had been another carbon atom on the other side of the C-Halogen bond, its hydrogen(s) would also be open to attack. If the haloalkane is unsymmetrical (e.g. 2-bromobutane) a mixture of isomeric alkene products is obtained.F H:@  :@   >   R  0 C *Aelimch1g R  0 C *A elimch2g   0 0T X (  W but-1-ene  3   0 0 H ,but-2-ene can exist as cis and trans isomers0- 3#&   B 0 s *޽h ? ̙33 0L0 g_ ,(  ,dB , <D)P0Q , 0Pp@ 0 0dB ,@ <D)PXP , 0X0@ 0 0 , 0q~ eUSES OF HALOGENOALKANES2(2ff  , 0T0 pSynthetic The reactivity of the C-X bond means that halogenoalkanes play an important part in synthetic organic chemistry. The halogen can be replaced by a variety of groups via nucleophilic substitution.< !@4  s    B , s *޽h ? ̙33  0L0   7 (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ eUSES OF HALOGENOALKANES2(2ff   0(0@  RSynthetic The reactivity of the C-X bond means that halogenoalkanes play an important part in synthetic organic chemistry. The halogen can be replaced by a variety of groups via nucleophilic substitution. Polymers Many useful polymers are formed from halogeno hydrocarbons Monomer Polymer Repeating unit chloroethene poly(chloroethene) PVC - (CH2 - CHCl)n  USED FOR PACKAGING tetrafluoroethene poly(tetrafluoroethene) PTFE - (CF2 - CF2)n - USED FOR NON-STICK SURFACES Xx@hPxUP$@!A.A   !F    !4  s   >  B     !      K B  s *޽h ? ̙33 0L0 /(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0ߎq~ eUSES OF HALOGENOALKANES2(2ff  00h Synthetic The reactivity of the C-X bond means that halogenoalkanes play an important part in synthetic organic chemistry. The halogen can be replaced by a variety of groups via nucleophilic substitution. Polymers Many useful polymers are formed from halogeno hydrocarbons Monomer Polymer Repeating unit chloroethene poly(chloroethene) PVC - (CH2 - CHCl)n  USED FOR PACKAGING tetrafluoroethene poly(tetrafluoroethene) PTFE - (CF2 - CF2)n - USED FOR NON-STICK SURFACES Chlorofluorocarbons - CFC s dichlorofluoromethane CHFCl2 refrigerant trichlorofluoromethane CF3Cl aerosol propellant, blowing agent bromochlorodifluoromethane CBrClF2 fire extinguishers CCl2FCClF2 dry cleaning solvent, degreasing agent All are/were chosen because of their LOW REACTIVITY, VOLATILITY, NON-TOXICITYFx@hPxUP@c*!#  $ "%   ())!*4  s   >  B     !      g    3   B  s *޽h ? ̙33Y 0L0 (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0 q~ eUSES OF HALOGENOALKANES2(2ffZ  08*0h Synthetic The reactivity of the C-X bond means that halogenoalkanes play an important part in synthetic organic chemistry. The halogen can be replaced by a variety of groups via nucleophilic substitution. Polymers Many useful polymers are formed from halogeno hydrocarbons Monomer Polymer Repeating unit chloroethene poly(chloroethene) PVC - (CH2 - CHCl)n  USED FOR PACKAGING tetrafluoroethene poly(tetrafluoroethene) PTFE - (CF2 - CF2)n - USED FOR NON-STICK SURFACES Chlorofluorocarbons - CFC s dichlorofluoromethane CHFCl2 refrigerant trichlorofluoromethane CF3Cl aerosol propellant, blowing agent bromochlorodifluoromethane CBrClF2 fire extinguishers CCl2FCClF2 dry cleaning solvent, degreasing agent All are/were chosen because of their LOW REACTIVITY, VOLATILITY, NON-TOXICITYx@hPxUP@ !!A.A   !F    9!#  $ "%   ())!*4  s   >  B     !      g    3   B  s *޽h ? ̙33 0L0 XP(    0\ *CFC s have been blamed for damage to the environment by thinning the ozone layer Ozone absorbs a lot of harmful UV radiation However it breaks down more easily in the presence of CFC's CFC s break up in the atmosphere to form radicals CF2Cl2   > CF2Cl" + Cl" Free radicals catalyse the breaking up of ozone 2O3   > 3O2<S33333333133 33&   D dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0$mq~ NPROBLEMS WITH CFC s AND THE OZONE LAYER2((2'ffB  s *޽h ? ̙33  0L0   : (  *  0s CFC s have been blamed for damage to the environment by thinning the ozone layer Ozone absorbs a lot of harmful UV radiation However it breaks down more easily in the presence of CFC's CFC s break up in the atmosphere to form radicals CF2Cl2   > CF2Cl" + Cl" Free radicals catalyse the breaking up of ozone 2O3   > 3O2S? &   D   0((g  DrCFC s were designed by chemists to help people Chemists are now having to synthesise alternatives to CFC s to protect the environment - Hydrocarbons and HCFC s are used for propellants - CO2 can be used as a blowing agent for making expanded polystyrene This will allow the reversal of the ozone layer problem@F@-9@f9 A7ff&   dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  04q~ NPROBLEMS WITH CFC s AND THE OZONE LAYER2((2'ffB  s *޽h ? ̙33l  0L0     ( w    0P *CFC s have been blamed for damage to the environment by thinning the ozone layer Ozone absorbs a lot of harmful UV radiation However it breaks down more easily in the presence of CFC's CFC s break up in the atmosphere to form radicals CF2Cl2   > CF2Cl" + Cl" Free radicals catalyse the breaking up of ozone 2O3   > 3O2<S33333333133 33&   D    0(g  DrCFC s were designed by chemists to help people Chemists are now having to synthesise alternatives to CFC s to protect the environment - Hydrocarbons and HCFC s are used for propellants - CO2 can be used as a blowing agent for making expanded polystyrene This will allow the reversal of the ozone layer problem@F@-9@f9 A7ff&   dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0Xq~ NPROBLEMS WITH CFC s AND THE OZONE LAYER2((2'ffB  s *޽h ? ̙336  0L0    Hd ( \0P H H 0 Ĕ  \There is a series of complex reactions but the basic process is :- " ozone in the atmosphere breaks down naturally O3   > O + O2 " CFC's break down in UV light to form radicals CCl2F2   > Cl" + CClF2" " chlorine radicals then react with ozone O3 + Cl"   > ClO" + O2 " chlorine radicals are regenerated ClO" + O   > O2 + Cl" Overall, chlorine radicals are not used up so a small amount of CFC's can destroy thousands of ozone molecules before they take part in a termination stage.CH@K@ @TK@C!!-.  '   !  ! !  L     ;     dB H <D)P0Q H 0Pp@ 0 0dB H@ <D)PXP H 0X0@ 0 0 H 0Dq~ NPROBLEMS WITH CFC s AND THE OZONE LAYER2((2'ffB H s *޽h ? ̙33^  0L0     (    0Ҕ JREVISION CHECK (2f  0  ZWhat should you be able to do? (2|   0` 8Recall and explain the physical properties of halogenoalkanes Recall and explain the chemical properties of halogenoalkanes based on their structure Recall and explain the properties of nucleophiles Write balanced equations for reactions involving substitution and elimination Understand how the properties of a hydroxide ion are influenced by the choice of solvent Recall the effect of CFC s on the ozone layer 2fffff,fff fEffffffffJf fOff(f>./?    0.   ~,CAN YOU DO ALL OF THESE? 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