ࡱ> 463iI @bjbjT~T~ 4T66 $+++++???8w|4?" '!!!!!!!$%Z(P!+!++f"4++!!: ,G!d-a?  !|"0" R(B(G!(+G!d!!"( :  Suppose you have discovered two new elements -- Quackine (Q) and Tweetine (T). You find they undergo a reaction with methane identical to free radical chain monohalogenation. Assuming the mechanisms are also identical, write the elementary steps for the reaction of Q2 or T2 with CH4. (Let X = Q or T). Use proper curved arrow formalism to represent the bonding changes taking place. Include the termination steps X = Q T 1  EMBED ChemDraw.Document.6.0  H1 = +79 +56 2a)  EMBED ChemDraw.Document.6.0  H2a = -15 +4 2b)  EMBED ChemDraw.Document.6.0  H2b = -3 -24 3a)  EMBED ChemDraw.Document.6.0  HT = -18 -20 3b)  EMBED ChemDraw.Document.6.0  3c)  EMBED ChemDraw.Document.6.0  a) Given the following homolytic bond dissociation energies (in Kcal/mol), calculate the enthalpy of reaction (H) for the first three steps in the mechanism. Place the values of H in the spaces provided on the problem above. Show all work. Q Q 79 CH3 Q 82 H Q 119 CH3 H 104 T T 56 CH3 T 80 H T 100 H1 = BDE(X-X); H2a = BDE(C-H) - BDE(H-X); H2b = BDE(X-X) - BDE(C-X) For Q : For T : H2a = 104 - 119 = -15 kcal/mol H2a = 104 - 100 = +4 kcal/mol H2b = 79 - 82 = -3 kcal/mol H2b = 56 - 80 = -24 kcal/mol b) Which of the two "halogens" would exhibit a more exothermic overall reaction with methane? Give the value of H for that "halogen". For Q : HT = -15 + (-3) = -18 kcal/mol For T : HT = +4 + (-24) = -20 kcal/mol (more negative) T more Exothermic ; H = -20 kcal/mol c) What is the rate-determining step (RDS) in the reaction of Q2 with CH4? Explain. For Q: H2b >H2a (less negative; less Exothermic) STEP 2b H2b (; TSE (; EA (; Rate ( Step 2b slower than step 2a therefore RDS d) What is the rate-determining step (RDS) in the reaction of T2 with CH4? Explain. For T: H2a > H2b (more positive; more Endothermic) STEP 2a H2a (; TSE (; EA (; Rate ( Step 2a slower than step 2b therefore RDS e) Which propagation step with which element would be expected to have the highest energy of activation? Explain H2a w/ T has the most Endothermic (positive) value (+4 kcal/mol) STEP 2a w/ T of all propagation steps H2a (; TSE (; EA ( therefore EA highest f) Which of the two "halogens" exhibits a greater reactivity (i.e. undergoes a faster reaction) towards methane? Explain. Exothermic Rxn; -H; R-Like TS ST         6 8 D F ˸ϫsle]RjIL h9nUVjh9nU hE,h% hE,h44hE,hE,OJQJ^JhE,hE,OJQJ^J hE,h%CJOJQJ^JaJhE,h%OJQJ^JhE,h%OJQJ^JjNIL hE,UVjhE,UhE,h9nh% h h@ h%h44H*h h H* h h44h%h%CJaJ 8 : < v x z   ` b  7$8$H$gd44 & F7$8$H$gd44 7$8$H$gd% , . 0 2 4 6 8 > @ T t ѳ딟뉁wѳpe]j)h9nUj;JL h9nUV hE,hE,h9nOJQJ^Jjh9nUjIL h9nUV hE,h9nh% hE,h%hE,hE,OJQJ^JhE,hE,OJQJ^J hE,h%CJOJQJ^JaJhE,h%OJQJ^JhE,h%OJQJ^Jh9njh9nUj h9nU#     X Z \ ^ ` j l  ^⶯zrkdYKYKYh%B*OJQJ^Jphh h44B*ph h h44 h h9njtEh9nUj_JL h9nUVh%j4h9nUjKJL h9nUVh9njh9nU h9nh9n hE,h%hE,hE,OJQJ^J hE,hE,CJOJQJ^JaJhE,hE,H*OJQJ^JhE,hE,OJQJ^J hE,hE,OJQJ^JmHsH^z 26>@BDH^bdjݱݥzzzss h9nhrh9nhrCJaJmHsHh9nhrmHsH h9nhrOJQJ^JmHsHh44B*mHphsHh h B*mHphsH h h B*H*mHphsHh B*mHphsHh h44B*mHphsHh h44B*phh%B*ph)>@x*,BP 7$8$H$gdr 7$8$H$gd44:<>Dxz|hjlnr(*,ǹDZݤݤuuj]h h B*H*phh hrB*ph h9nhrCJOJQJ^JaJh9nhrOJQJ^J h9nhrCJOJQJ^JaJh9nhrOJQJ^Jh44B*phh%B*OJQJ^Jphh h44B*phhrhrB*ph h9nhrOJQJ^JmHsH h9nhrh9nhrCJaJ$BVXZ`bnpvz|ƹvffYI jh9nhrOJQJ^Jh9nhrOJQJ^J jh9nhrOJQJ^J jh9nhrOJQJ^J h9nhrCJOJQJ^JaJ h9nhrCJOJQJ^JaJ h9nhrOJQJ^JmHsHh9nhrOJQJ^JhrB*OJQJ^Jphh%h44B*phh%B*phh h B*H*phh h44B*phhjz|"ööïyhWF h9nhqCJOJQJ^JaJ h9nhqOJQJ^JmHsH h9nhqCJOJQJ^JaJ h9nhr h9nhrCJOJQJ^JaJ h9nhrOJQJ^JmHsHh9nhqOJQJ^J h9nh44h h B*H*phh h44B*phh hrB*phh9nh44OJQJ^Jh9nhrOJQJ^Jh9nhrOJQJ^J"$028<>JLNP2dlntv㵥㞗uc#hqB*CJOJQJ^JaJph h9nhqCJOJQJ^JaJ h9nhqOJQJ^JmHsH h9nh44 h9nhr jh9nhqOJQJ^Jh9nhqOJQJ^J h9nhqCJOJQJ^JaJ jh9nhqOJQJ^Jh9nhqOJQJ^J jh9nhqOJQJ^J$d2 333333 4 44455&7(7|7~77 7$8$H$gd 7$8$H$gdq 7$8$H$gd442222 2 33333j33 44<4>4@4ϾܭϚό~q`RDRϾhqB*OJQJ^JphhqB*OJQJ^Jph!hqhqB*OJQJ^JphhqhqOJQJ^Jh9nB*OJQJ^JphhqB*OJQJ^Jph h9nhqCJOJQJ^JaJU h9nhqCJOJQJ^JaJ h9nhqOJQJ^JmHsHh9nhqOJQJ^J h9nhq h9nh44 h h44hqB*OJQJ^JphEP 2b w/ T H2b w/ T has the most Exothermic (negative) value (-24 kcal/mol) of all steps Most Exothermic = Most Reactant-Like g) Which of the two "halogens" exhibits a greater reactivity (i.e. undergoes a faster reaction) towards methane? Explain. RDS for Q = Step 2b; H2b = -3 kcal/mol Z More Exothermic Q more Reactive RDS for T = Step 2a; H2a = +4 kcal/mol H2b (; TSE (; EA (; Rate ( for Q therefore Q faster overall reaction h) Draw a reaction-energy profile for the rate-determining step (RDS) in the reaction of T2 with CH4. Label the reactants, products, enthalpy (H), energy of activation (EA) and the transition state (TS). RDS = Step 2a; For T ( +Ho (Endothermic)  i) Draw an accurate structural depiction of the transition state for the rate-determining step (RDS) in the reaction of Q2 with CH4. RDS = Step 2b; For Q ( -H (Exothermic)  EMBED ChemDraw.Document.6.0  TS = R-Like j) Which of the two "halogens" would be expected to produce a greater percentage of n-propyl "halide" isomer upon reaction with propane? Explain. CH3CH2CH2-X (1o H s) Q2 more reactive; less selective - chooses more numerous 1o H s (6 H s) You have discovered yet another new element, Kitcarsine, Kc. It also undergoes normal monohalogenation reactions as shown below.  EMBED ChemDraw.Document.6.0  From the yields shown, calculate the relative reactivities of primary, secondary and tertiary hydrogens (1o: 2o: 3o H) towards Kc2. Show all work. 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@ >]EjGD}fE22D: $$==_888 % % W$5pPl#$ % % $$AA( : Fl`EMF+@0$BARIAL@, 2PECC   % TTBQAAOLPC % F`TEMF+*@$??@, SECH   % TTB&QAAOLPH % FEMF+*@$??@0$۫zBARIAL@, WEZ]C3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TT(H-TAA(RLP3% FEMF+*@$??@@4VA? @ RE,DREX)D: $$==_888 % % W$Pp!!#% % $$AA( : Fl`EMF+@0$BARIAL@, [EhDC   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT2:AA2LPC % F`TEMF+*@$??@, s_EhDH   % TT<DAA<LPH % FEMF+*@$??@0$۫zBARIAL@, 3cEQqD3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTEJAAELP3% FEMF+*@$??@@4VA? @ >]EjGD>]EhD: $$==_888 % % W$5}9l#l#A % % $$AA( : Fl`EMF+@0$BARIAL@, a~yE:"DK   ( RpArialD?`H?h<S"| 8S M?VDNϪDϪDNDHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT~fuAA~sLPK % FEMF+*@$??@0$۫zBARIAL@,  |Eُ+Dc   ( RpArialD?`H?h<S"| 8S M?DNDDND0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTlxAAvLPc% FEMF+*@$??@@4VA? @ :mE,DxE,D: $$==_888 % % W$_lp &'% % $$AA( : FtEMF+@D8BTIMES NEW ROMAN@, fPEqD2   ( RpTimes New RomanD?`H?h<S"| 8S M?DNDDNDHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTAALP2% F`TEMF+*@$??@, SEqD0   % TT$AALP0% F`TEMF+*@$??@, VEqD%   % TT%1AA%LP% % FEMF+*@$??@0$BARIAL@, UC`DH   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT-5 AA- LPH % FEMF+*@$??@0$۫zBARIAL@, UC D3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TT6;AA6LP3% FEMF+*@$??@0$BARIAL@, UC`DC   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT<D AA< LPC % FEMF+*@$??@@4VA? @ CDhDD: $$==_888 % % W$Eem3% % $$AA( : FpdEMF+@@4VA? @ hDDQDD: $$==_888 % % W$a3]X% % $$AA( : Fl`EMF+@0$BARIAL@, F:DDC   % TTAALPC % F`TEMF+*@$??@, FDDH   % TTAALPH % FEMF+*@$??@0$۫zBARIAL@, F:DjD3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALP3% FEMF+*@$??@@4VA? @ QDD}DtD: $$==_888 % % W$]X T% % $$AA( : FtEMF+@D8BTIMES NEW ROMAN@, D:Dl   ( RpTimes New RomanD?`H?h<S"| 8S M?9DN_D_DN?DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTvAALPl% F`TEMF+*@$??@, pD:Di   % TTvAALPi% F`TEMF+*@$??@, D:Dg   % TTvAALPg% F`TEMF+*@$??@,  D:Dh   % TTvAALPh% F`TEMF+*@$??@, `D:Dt   % TTvAALPt% FEMF+*@$??@@4V?? @ DDDD: $$==_888 % % W$ % % $$AA( : F4(EMF+ @$`DD CA$$==% % V0   % % $$AAFEMF+ @DDkmD/DU?D{D@D\DDbDD1DDIDDDUuDDDDkD6sDD+DDD3YDhDDDXDDXDDD"D3YDsDDDkD'DDdDDpDDzDDC1DDD@D3DU?DDkmDhDDD$$==%  % VuN''Nu%  % $$AAFEMF+@@4V??@xl DDDDUuDDUuDDUuDDD8DDDDDUuDqRDUuDqRDUuDqRDDDDD: $$==_888 % % UP  % % $$AA( : FtEMF+@D8BTIMES NEW ROMAN@, DD(   % TTAALP(% F`TEMF+*@$??@, UDDK   % TTAALPK % FEMF+*@$??@D8UUBTIMES NEW ROMAN@, UDDc   ( RpTimes New RomanD?`H?h<S"| 8S M?DN_cD_cDN?cD0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALPc% FEMF+*@$??@D8BTIMES NEW ROMAN@, ҺDD)   ( RpTimes New RomanD?`H?h<S"| 8S M?DN*D*DN*DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTAALP)% FEMF+*@$??@D8UUBTIMES NEW ROMAN@, DD2   ( RpTimes New RomanD?`H?h<S"| 8S M?DNDDND0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALP2% FEMF+*@$??@D8BTIMES NEW ROMAN@, DrDl   ( RpTimes New RomanD?`H?h<S"| 8S M?9DN_D_DN?DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTAALPl% F`TEMF+*@$??@, DrDi   % TTAALPi% F`TEMF+*@$??@, DrDg   % TTAALPg% F`TEMF+*@$??@, ȹDrDh   % TTAALPh% F`TEMF+*@$??@, DrDt   % TTAALPt% FEMF+*@$??@0$BARIAL@, (DUWDH   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT;C AA;LPH % FEMF+*@$??@0$۫zBARIAL@, DD3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTDI AAD LP3% FEMF+*@$??@0$BARIAL@, EUWDC   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTJR AAJLPC % FEMF+*@$??@@4VA? @ TEDgEUD: $$==_888 % % W$SsN% % $$AA( : FpdEMF+@@4VA? @ gEUD EUD: $$==_888 % % W$o>% % $$AA( : Fl`EMF+@0$BARIAL@, )E8DH   % TTAALPH % FEMF+*@$??@0$۫zBARIAL@, X-EfD2   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALP2% FEMF+*@$??@0$BARIAL@, )EqִDC   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTAALPC % FEMF+*@$??@@4VA? @  EUD(ED: $$==_888 % % W$>% % $$AA( : Fl`EMF+@0$BARIAL@, 4E/DK   % TTAALPK % FEMF+*@$??@0$۫zBARIAL@, ?8EzDc   ( RpArialD?`H?h<S"| 8S M?DNDDND0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALPc% FEMF+*@$??@@4VA? @ -EfDZ-4EqD: $$==_888 % % W$7?% % $$AA( : FtEMF+@D8BTIMES NEW ROMAN@, ED2   ( RpTimes New RomanD?`H?h<S"| 8S M?DNDDNDHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTqx0AAq-LP2% F`TEMF+*@$??@, ED0   % TTy0AAy-LP0% F`TEMF+*@$??@, ED%   % TT0AA-LP% % FEMF+*@$??@0$BARIAL@, NMEU߾DH   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT AA LPH % FEMF+*@$??@0$۫zBARIAL@, QED3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALP3% FEMF+*@$??@0$BARIAL@, 9SEU߾DC   ( RpArialD?`H?h<S"| 8S M?DNDDN߸DHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT$AALPC % FEMF+*@$??@@4VA? @ WEXDbEUD: $$==_888 % % W$%Fv"p;$j% % $$AA( : FpdEMF+@@4VA? @ bEUD *pEU/D: $$==_888 % % W$Bh;$jf&% % $$AA( : Fl`EMF+@0$BARIAL@, {EU?DC   % TTAALPC % F`TEMF+*@$??@, EU?DH   % TTAALPH % FEMF+*@$??@0$۫zBARIAL@, ~ED3   ( RpArialD?`H?h<S"| 8S M?sDNoDoDN_D0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTAALP3% FEMF+*@$??@@4VA? @  *pEU/D*{EzD: $$==_888 % % W$df&((% % $$AA( : Fl`EMF+@0$BARIAL@,  6nEUDK   ( RpArialD?`H?h<S"| 8S M?VDNϪDϪDNDHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TTai*AAa(LPK % FEMF+*@$??@0$۫zBARIAL@, qEDc   ( RpArialD?`H?h<S"| 8S M?DNDDND0xS$|`|]|| | P @wPwؚ|| |wP !h+w @w dv% TTj!n-AAj+LPc% FEMF+*@$??@@4VA? @  *pEU/D *pEUD: $$==_888 % % W$dhf&f&% % $$AA( : FtEMF+@D8BTIMES NEW ROMAN@, [ED8   ( RpTimes New RomanD?`H?h<S"| 8S M?DNDDNDHxS<|`|]|| | P @wwؚ|| |wP !+w @w dv% TT2!93AA20LP8% F`TEMF+*@$??@, ^ED0   % TT:!A3AA:0LP0% F`TEMF+*@$??@, aED F`TEMF+*@$??@, cED%   % TTF!R3AAF0LP% % F<0EMF+*@$??@ CDIFVjCD0100ChemDraw 11.0z,!J  @@' :;E<  BCD `  3xx# $$$$2$ArialTimes New RomanxXXjdVg(XXd'`k$$z,H5r=xW@D Q+7f[GffTH5]G#`CH3KiUZ RWjp TK= V+7fN=fG=,Q=x#`CH3 /iUZ X+7z3iVz,iV6iMi#`CH3 :ljp Z+7plrilrb#`CH3 S  U  W  Y  [ -gEqsrH?8X_ ^+7\Tg e^#`CH3?xKJu  _?8X  a?xK6 c+7^O3H3 QE#`CH3Sh0Ju  e+7N4J-J6Jm#`CH3yDm  g+7*qiEqs/#`CH3$aA i&ChemDraw can't interpret this label.7> e>]> XgrH#` Kc `  b  d  f  h  j "4GnEz`#?_?} l+7c׀^\Gn e׀#`CH3$?RJU m%?_j o&?R q+7SL-EWD#`CH2'S7JU s+7;J4J>JM#`CH3(ytj u+7ߪxҥjqҥEzb#`CH3.?R  w&ChemDraw can't interpret this label.7V ?O r+Y`#` Kc) n#$ * p$% + r%& , t$' - v%( / x&. 9f&!̬980 z+7ffX4f&!̬X4#`CH3:J {7<&d }7>9~ +7ff9{f&9{̬9#`CH3; |8: = ~:< ? 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