Organic Chemistry, 7e (Wade) 7e (Wade) Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination
1) Which of the following best describes the carbon-chlorine bond of an alkyl chloride? A) nonpolar; no dipole B) polar; d+ at carbon and d- at chlorine C) polar; d- at carbon and d+ at chlorine D) ionic ) none of the abo!e Answer" B Diff" 1 #ection" $%1 &) Which of the following is classified as a !inylic halide? A) C'(C'C'*' B) C'(C'C'Cl C) C'(C'C'C'&Cl D) C'(C'&C'&C'&Br ) BrC'&C'C'& Answer" B Diff" 1 #ection" $%1 () he fla,e retardant below has been fond to be an androgen agonist and ,ay ha!e a contribtion to an increasing rate of occrrence of prostate cancer J. .J. Med. Chem. 26/ 0($$)% What is the correct ter, that describes the relati!e position of the bro,ides in this strctre?
A) ge,inal B) !inyl C) !icinal D) aryl Answer" C Diff" 1 #ection" $%&
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) What general classification is gi!en to the ,olecle below?
A) pri,ary chloride B) secondary chloride C) tertiary chloride D) !inyl chloride ) ben2yl chloride Answer" C Diff" 1 #ection" $%& 3) Which of the following is a ge,inal dihalide? A) cis-1/&-dibro,ocyclopentane B) (/(-dichloropentane C) trans-1/-diiodocyclohe4ane D) isobtyl chloride ) 1/(-dibro,oheptane Answer" B Diff" & #ection" $%& $) Which of the following is a !icinal dihalide? A) cis-1/&-dibro,ocyclopentane B) (/(-dichloropentane C) trans-1/-diiodocyclohe4ane D) isobtyl chloride ) 1/(-dibro,oheptane Answer" A Diff" & #ection" $%& 0) Which of the following is a secondary alkyl halide? A) ,ethyl bro,ide B) isopropyl chloride C) t -btyl -btyl iodide D) propyl bro,ide ) isobtyl chloride Answer" B Diff" & #ection" $%&
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) What general classification is gi!en to the ,olecle below?
A) pri,ary chloride B) secondary chloride C) tertiary chloride D) !inyl chloride ) ben2yl chloride Answer" C Diff" 1 #ection" $%& 3) Which of the following is a ge,inal dihalide? A) cis-1/&-dibro,ocyclopentane B) (/(-dichloropentane C) trans-1/-diiodocyclohe4ane D) isobtyl chloride ) 1/(-dibro,oheptane Answer" B Diff" & #ection" $%& $) Which of the following is a !icinal dihalide? A) cis-1/&-dibro,ocyclopentane B) (/(-dichloropentane C) trans-1/-diiodocyclohe4ane D) isobtyl chloride ) 1/(-dibro,oheptane Answer" A Diff" & #ection" $%& 0) Which of the following is a secondary alkyl halide? A) ,ethyl bro,ide B) isopropyl chloride C) t -btyl -btyl iodide D) propyl bro,ide ) isobtyl chloride Answer" B Diff" & #ection" $%&
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5) Which of the following is a pri,ary alkyl halide? A) ,ethyl bro,ide B) isopropyl bro,ide C) t -btyl -btyl iodide D) cyclohe4yl bro,ide ) isobtyl chloride Answer" Diff" & #ection" $%& 6) What is the 789AC na,e of the co,pond shown below?
A) .1#/(#)-1/(-dichloro-1-ethyl-(-,ethylcyclopentane B) .1:/(#)-1/(-dichloro-1-,ethyl-(-ethylcyclopentane C) .1:/#)-1/-dichloro-1-ethyl--,ethylcyclopentane D) .1:/(#)-1/(-dichloro-1-ethyl-(-,ethylcyclopentane ) .1#/(:)-1/(-dichloro-(-ethyl-1-,ethylcyclopentane Answer" D Diff" & #ection" $%& 1) What is the 789AC of the co,pond shown below?
A) .&:/(#/#)-&-chloro-(/-dibro,o-(-,ethylhe4ane B) .&:/(#/#)-(/-dibro,o-&-chloro-(-,ethylhe4ane C) .(#/#/3#)-(/-dibro,o-3-chloro--,ethylhe4ane D) .&:/(:/#)-(/-dibro,o-&-chloro-(-,ethylhe4ane ) .&:/(#/:)-(/-dibro,o-&-chloro-(-,ethylhe4ane Answer" B Diff" & #ection" $%&
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11) 9ro!ide the na,e of the bro,oalkane shown below%
Answer" (-bro,o--ethylheptane Diff" 1 #ection" $%& 1&) Draw the strctre of cis-1/(-dichlorocyclopentane% Answer"
Diff" 1 #ection" $%& 1() 9ro!ide an acceptable na,e for C'Cl(% Answer" chlorofor, or trichloro,ethane Diff" 1 #ection" $%& 1) 9ro!ide an acceptable na,e for C'(C'&C'&C.C'()&7% Answer" &-iodo-&-,ethylpentane Diff" 1 #ection" $%& 13) 9ro!ide an acceptable na,e for the co,pond shown below%
Answer" cis-1/ &-dichlorocyclopentane Diff" 1 #ection" $%& 1$) 9ro!ide the strctre of isopropyl iodide% Answer" .C'()&C'7 Diff" 1 #ection" $%&
10) 9ro!ide an acceptable na,e for the co,pond shown below%
Answer" -bro,o-1/1-di,ethylcyclohe4ane Diff" & #ection" $%& 15) 9ro!ide the strctre of 1-bro,o-(-,ethylhe4ane% Answer" C'(C'&C'&C'.C'()C'&C'&Br Diff" & #ection" $%& 16) Which of the following best describes DD? A) a chlorocarbon sed to decaffeinate coffee beans B) a polybro,inated organic co,pond sed as a herbicide C) a
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&&) Althogh < is ,ore electronegati!e than Cl/ the C-Cl bond has a larger dipole ,o,ent than the C-< bond% 4plain% Answer" he bond dipole ,o,ent is deter,ined by a prodct of the a,ont of charge separation and the distance o!er which the charge is separated/ > %5 4 4 d% Althogh is larger in the C-< bond/ the greater length of the C-Cl bond lti,ately ,akes its dipole ,o,ent larger% Diff" ( #ection" $% &() A,ong the following alkyl halides/ choose the one with the lowest boiling point% A) t -btyl chloride B) n-btyl chloride C) t -btyl bro,ide D) n-btyl iodide ) t -btyl iodide Answer" A Diff" & #ection" $%3 &) Arrange the following alkyl halides in order of increasing boiling point" C'(C'&Br/ C'(C'&C'&Br/ .C'()&C'Br/ C'(C'&<% Answer" C'(C'&< @ C'(C'&Br @ .C'()&C'Br @ C'(C'&C'&Br Diff" & #ection" $%3 &3) When water is shaken with dichloro,ethane/ a two-phase syste, reslts% Which co,pond for,s the pper phase? 4plain% Answer" Water is less dense than dichloro,ethane and therefore for,s the pper phase% Diff" & #ection" $%3 &$) When &/&-di,ethylbtane is sbected to free-radical chlorination/ ========== distinct ,onochlorinated prodcts are possible and ========== of these contain asy,,etric carbon ato,s% A) / & B) 3/ C) (/ D) 3/ & ) / Answer" A Diff" & #ection" $%$
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&0) Draw two reasonable resonance strctres and the hybrid of the inter,ediate for,ed in the following reaction%
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Diff" & #ection" $%$ &5) 9ro!ide the ,aor organic prodct of the reaction below%
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&6) Draw the strctres of the two ,aor prodcts for,ed in the following reaction% 7ndicate which of the two strctres wold be predicted to predo,inate nder ther,odyna,ic condition and e4plain why%
Answer" :eacti!ity of allylic hydrogens de to resonance stability of the radical inter,ediate wold reslt in the the for,ation of two ,aor sbstittion prodcts"
1 & 9rodct & .1-bro,o,ethyl-cyclohe4ene) wold be predicted to predo,inate in this reaction becase it wold for, the ,ore sbstitted alkene% 'owe!er/ radical characterists on the secondary carbon ,ay lead to a significant for,ation of prodct 1 Diff" ( #ection" $%$ () 9ro!ide the strctre of the ,aor organic prodct in the reaction below%
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Diff" & #ection" $%$
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(1) 9ro!ide the strctre of the ,aor organic prodct in the reaction below%
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Diff" & #ection" $%$ (&) What type of inter,ediate is present in the # & reaction of cyanide with bro,oethane? A) carbocation B) free radical C) carbene D) carbanion ) his reaction has no inter,ediate% Answer" Diff" & #ection" $%5 (() Consider the reaction of .C'()(C*- with iodo,ethane% Will the reaction rate increase/ decrease/ or re,ain the sa,e if the concentration of iodo,ethane is increased? 4plain% Answer" his is an # & reaction with a rate kE.C'()(C*-F EC'(7F% he reaction rate will increase as EC'(7F increases% Diff" 1 #ection" $%5 () 9ro!ide a detailed/ stepwise ,echanis, for the reaction below% .C'()&C'C'&C'&C'&7 + C- G .C'()&C'C'&C'&C'&C'&C + 7Answer"
Diff" & #ection" $%5
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(3) 9ro!ide the strctre of the ,aor organic prodct that reslts when the reagents below are co,bined/ and na,e the ,echanis, throgh which this reaction is proceeding% C'(C C:- a+ + C'(C'&C'&7 Answer" C'(C CC'&C'&C'(/ # & Diff" & #ection" $%6 ≡
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($) 9ro!ide the strctre of the ,aor organic prodct in the following reaction% .C'()( + C'(C'&C'&7 G Answer" E.C'()( C'&C'&C'(F+ 7Diff" & #ection" $%6 (0) Which of the following species is the least ncleophilic? A) '&* B) B<( C) .C'()( D) C'(*) CAnswer" B Diff" & #ection" $%1 (5) Which of the following co,ponds is the ,ost ncleophilic? A) C'(#' B) C'(*' C) '&* D) C'(C*&' ) B<( Answer" A Diff" & #ection" $%1 (6) Which of the following sol!ents cold be described a s polar and protic? A) ethanol B) acetonitrile C) di,ethylfor,a,ide D) acetone ) 15-crown-$ Answer" A Diff" ( #ection" $%1
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) a,e one factor that is fa!orable for ncleophilicity bt not for basicity% Answer" polari2ability Diff" & #ection" $%1 1) Arrange the following species in order of increasing ncleophilicity" C'(C'&#-/ C'(C'&*-/ .C'()(C*-/ .C'()(C*'% Answer" .C'()(C*' @ .C'()(C*- @ C'(C'&*- @ C'(C'&#Diff" & #ection" $%1 &) Which halide is a better ncleophile/ iodide or floride? 4plain% Answer" he iodide ion is the better ncleophile% he larger si2e of this ion renders its electron clod ,ore polari2able% Diff" & #ection" $%1 () Which is ,ore ncleophilic/ t-bto4ide or etho4ide? 4plain% Answer" tho4ide is the better ncleophile% he steric blk of t-bto4ide decreases its effecti!eness as a nlcoephile% Diff" & #ection" $%1 ) :ank the species below in order of increasing ncleophilicity in hydro4ylic sol!ents" C'(C*&-/ C'(#-/ '*-/ '&*% Answer" '&* @ C'(C*&- @ '*- @ C'(#Diff" & #ection" $%1 3) What type of sol!ent is best for # & reactions which e,ploy anionic ncleophiles" polar/ protic sol!ents; polar/ aprotic sol!ents; or nonpolar sol!ents? 4plain% Answer" 9olar/ aprotic sol!ents are best% hese sol!ents ha!e strong dipole ,o,ents to enhance solbility of the anionic species bt lack the ability to sol!ate the anion by hydrogen bonding% Diff" ( #ection" $%1 $) Which of the following co,ponds will ndergo an # & reaction ,ost readily? A) .C'()(CC'&7 B) .C'()(CCl C) .C'()&C'7 D) .C'()&C'C'&C'&C'&7 ) .C'()&C'C'&C'&C'&Cl Answer" D Diff" & #ection" $%11 11
0) Which of the following alkyl chlorides will ndergo # & reaction ,ost readily? A) 1-chloro--,ethylpentane B) &-chloro--,ethylpentane C) &-chloro-(-,ethylpentane D) (-chloro-&-,ethylpentane ) &-chloro-&-,ethylpentane Answer" A Diff" & #ection" $%11 5) Arrange the following sbstrates in order of their increasing #& reacti!ity with aC" bro,oethane/ 1-chloro-(/(-di,ethylpentane/ 1-chloro-&/&-di,ethylpentane/ and &-bro,o-&,ethylpentane% Answer" &-bro,o-&-,ethylpentane @ 1-chloro-&/&-di,ethylpentane @ 1-chloro-(/(di,ethylpentane @ bro,oethane Diff" & #ection" $%11 6) Hist the following bro,ides in order of their increasing reacti!ity as sbstrates in # & reactions" 9hBr/ 9hC'&Br/ and 9hC'.C'()Br% Answer" 9hBr @ 9hC'.C'()Br @ 9hC'&Br Diff" & #ection" $%11 3) Hist the following bro,ides in order of their increasing reacti!ity as sbstrates in # & reactions" &-chlorobtane/ &-iodobtane/ and 1-iodobtane% Answer" &-chlorobtane @ &-iodobtane @ 1-iodobtane Diff" & #ection" $%11 31) Do all pri,ary iodides react with (- at the sa,e rate !ia the # & ,echanis,? 4plain% Answer" o/ not all pri,ary alkyl react with (- at the sa,e rate !ia the # & ,echanis,% #o,e pri,ary iodides are ,ore hindered than others% .C'()(CC'&7 and C'(C'&7 are both pri,ary/ bt .C'()(CC'&7 is significantly ,ore hindered% Additionally/ so,e pri,ary iodides ha!e increased acti!ity de to a ben2ylic or allylic positioning% Diff" & #ection" $%11 3&) Do all pri,ary alkyl iodides ndergo # & reactions with sodi, cyanide in DI#* at identical rates? 4plain% Answer" o% All pri,ary iodides are not eJally accessible to attack by the C-% #teric hindrance !aries a,ong pri,ary iodides% Diff" & #ection" $%11
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3() Which of the following alkyl chlorides wold ndergo sbstittion ,ost rapidly when treated + -
with a C C' chloroethane &-chloropropane or 1-chloro-&/&-di,ethylpropane 9ro!ide the strctre of the sbstittion prodct% Answer" C'(C'&C C' Diff" & #ection" $%11 ≡
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3) #how the best way to prepare C'(*C'.C'()& by an # & reaction% Answer" C'(7 + a*C'.C'()& Diff" & #ection" $%11 33) # & reactions take place with ========== of stereoche,istry at the center ndergoing sbstittion% Answer" in!ersion Diff" 1 #ection" $%1& 3$) Co,plete the following # & reaction by pro!iding strctres for the necessary starting ,aterials%
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Diff" & #ection" $%1& 30) 9ro!ide the ,aor organic prodct of the reaction below%
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35) 9ro!ide the ,aor organic prodct of the reaction below%
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Diff" & #ection" $%1& 36) 9ro!ide the ,aor organic prodct of the reaction below%
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Diff" & #ection" $%1& $) 9ro!ide the strctre of the ,aor organic prodct which reslts when .S )-&-iodopentane is treated with KC in DI<% Answer"
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$1) 9ro!ide the strctre of the ,aor organic prodct in the following reaction%
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Diff" & #ection" $%1& $&) Which of the co,ponds below ndergoes sol!olysis in aJeos ethanol ,ost rapidly? A) cyclohe4yl bro,ide B) ,ethyl iodide C) isopropyl chloride D) (-chloropentane ) (-iodo-(-,ethylpentane Answer" Diff" & #ection" $%1( $() Which of the following alkyl bro,ides ndergoes sol!olysis in aJeos ,ethanol ,ost rapidly? A) 9hC'BrC'( B) .C'()&C'C'&C'&Br C) .C'()&C'C'&C'BrC'( D) C'(C'&C'&C'&Br ) 9hBr Answer" A Diff" & #ection" $%1(
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$) :ank the following ,olecles in order of increasing relati!e rate of # 1 sol!olysis with ,ethanol and heat .slowest to fastest reacting)%
A) ( @ & @ @ 3 @ 1 B) & @ ( @ @ 1 @ 3 C) 3 @ @ ( @ & @ 1 D) & @ ( @ @ 3 @ 1 ) 1 @ & @ 3 @ @ ( Answer" B Diff" ( #ection" $%1( $3) Arrange the following co,ponds in order of increasing reacti!ity toward ethanol sol!olysis" t -btyl bro,ide/ t -btyl iodide/ isopropyl chloride/ ,ethyl iodide% Answer" ,ethyl iodide @ isopropyl chloride @ t -btyl bro,ide @ t -btyl iodide Diff" & #ection" $%1( $$) Hist the following bro,ides in order of their increasing reacti!ity as sbstrates in # 1 reactions" 9hBr/ 9hC'&Br/ and 9hC'.C'()Br% Answer" 9hBr @ 9hC'&Br @ 9hC'.C'()Br Diff" & #ection" $%1( $0) Hist the following bro,ides in order of their increasing reacti!ity as sbstrates in # 1 reactions" &-chlorobtane/ &-iodobtane/ and 1-iodobtane% Answer" 1-iodobtane @ &-chlorobtane @ &-iodobtane Diff" & #ection" $%1( $5) Hist the following bro,ides in order of their increasing reacti!ity as sbstrates in # 1 reactions" 1-iodo-1-ethylcyclopentane/ chlorocyclopentane/ and iodocyclopentane% Answer" chlorocyclopentane @ iodocyclopentane @ 1-iodo-1-ethylcyclopentane Diff" & #ection" $%1(
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$6) Draw the highest energy transition state in the sol!olysis of .C'()(C7 in C'(*'% Answer"
Diff" & #ection" $%1( 0) Hist the following co,ponds in order of increasing reacti!ity in an # 1 reaction% C'(Br/ C'(C'&C'&7/ .C'()(C7/ C'(C'BrC'(/ C'(C'7C'( Answer" C'(Br @ C'(C'&C'&7 @ C'(C'BrC'( @ C'(C'7C'( @ .C'()(C7 Diff" & #ection" $%1( 01) When t -btyl chloride ndergoes sol!olysis in a sol!ent ,i4tre co,posed of 0L waterM(L acetone/ the reaction rate is slower then when the sa,e co,pond is sol!oly2ed in 5L waterM&L acetone% 4plain% Answer" his is prely a sol!ent effect% he greater the percentage of water in this sol!ent ,i4tre/ the ,ore polar the sol!ent% he ,ore polar the sol!ent/ the ,ore easily sol!ated the de!eloping carbocation and the ,ore rapidly it is for,ed% Diff" ( #ection" $%1( 0&) When ioni2ation occrs at the single sterocenter of a chiral co,pond/ the reslting carbocation is" A) achiral B) chiral C) race,ic D) optically acti!e ) none of the abo!e Answer" A Diff" & #ection" $%1 0() # 1 reactions sally proceed with" A) eJal a,onts of in!ersion and retention at the center ndergoing sbstittion% B) slightly ,ore in!ersion than retention at the center ndergoing sbstittion% C) slightly ,ore retention then in!ersion at the center n dergoing sbstittion% D) co,plete in!ersion at the center ndergoing sbstittion% ) co,plete retention at the center ndergoing sbstittion% Answer" B Diff" ( #ection" $%1 10
0) 7f the absolte configration at an asy,,etric carbon does not change dring the corse of a reaction/ the reaction is said to occr with ========== of stereoche,istry% Answer" retention Diff" 1 #ection" $%1 03) 9ro!ide the strctre of the ,aor organic prodcts which reslt in the reaction below%
Answer"
Diff" & #ection" $%1 0$) 9ro!ide two circ,stances nder which sol!olysis of a chiral alkyl halide wold not reslt in the generation of a ,i4tre of enantio,eric prodcts% Answer" Choose fro, a,ong" .i) lea!ing grop not bond to stereocenter .ii) rearrange,ent yields a carbocation in which two grops bond to the cationic center are the sa,e .iii) the ,olecle contains at least one additional stereocenter which is naffected by the ioni2ation .i!) rearrange,ent lti,ately reslts in a ,eso co,pond Diff" ( #ection" $%1 00) Which of the cations below wold be sbect to a strctral rearrange,ent?
A) 1 B) ( C) 1/ &/ N ( D) & N ( Answer" B Diff" & #ection" $%13
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05) Which of the following alkyl halides is ,ost likely to ndergo rearrange,ent in an # 1 reaction? A) (-bro,opentane B) &-chloro-(/(-di,ethylpentane C) (-chloropentane D) bro,ocyclohe4ane ) 1-bro,o--,ethylcyclohe4ane Answer" B Diff" & #ection" $%13 06) Which of the following alkyl chlorides is least likely to ndergo rearrange,ent dring a sol!olysis reaction? A) &-chloro--,ethylpentane B) &-chloro-(-,ethylpentane C) &-chloro-&-,ethylpentane D) cis-1-chloro-&-ethylcyclohe4ane ) trans-1-chloro-&-ethylcyclohe4ane Answer" C Diff" & #ection" $%13 5) A sa,ple of 1-chloro-1-phenylethane with an EOF&3D of -6%5P is reacted with '( in ,ethanolMwater sol!ent% he ,aor sbstittion prodct of the reaction is 1-phenyl-1-ethyla,ine with an EOF&3D of -5%$P% Qi!en that optically pre .:) 1-chloro-1-phenylethane has a specific rotation of -16%P and that optically pre .:) 1-phenyl-1-ethyla,ine has a specific rotation of +(6%(P/ which of the following state,ents best describes this reaction?
A) et in!ersion &3L with 03L race,i2ation -B) et in!ersion 1&L with 55L race,i2ation -C) et in!ersion 03L with &3L race,i2ation -D) et in!ersion 1&L with 55L race,i2ation -) et in!ersion 55L with 1&L race,i2ation -Answer" A Diff" ( #ection" $%13
# 1 ,echanis, # 1 ,echanis, # & ,echanis, # & ,echanis, # & ,echanis,
16
51) 9redict the strctre of the e4pected prodct for the following reaction%
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Diff" ( #ection" $%13 5&) 9ro!ide the ,aor organic prodct of the reaction below and a detailed/ stepwise ,echanis, which acconts for its for,ation%
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Diff" ( #ection" $%13
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5() 9ro!ide the strctre of the ,aor organic prodct which reslts in the following reaction%
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Diff" ( #ection" $%13 5) Which of the following state,ents correctly describe.s) 1 reactions of alkyl halides .:R)? 7% :ate kEbaseF 77% :ate kEbaseFE:RF 777% :ate kE:RF 7S% he reactions occr in two or ,ore distinct steps% S% :earrange,ents are so,eti,es seen% A) 77 and 7S B) 777 and S C) 7/ 7S/ and S D) 7 only ) 777/ 7S/ and S Answer" Diff" & #ection" $%10 53) Why does C'&C'C'BrC'( ndergo sol!olysis ,ch ,ore rapidly than &-bro,obtane? Answer" he inter,ediate carbocation is resonance stabili2ed% Diff" ( #ection" $%10
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5$) When 1-bro,o-&/ &-di,ethylcyclopentane is heated in ethanol/ one of the prodcts which reslts is shown below% 9ro!ide a detailed/ stepwise ,echanis, for the prodction of this co,pond/ and gi!e the na,e of the ,echanis, by which it is prodced%
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Diff" ( #ection" $%10 50) Dehydration of 1-btanol with concentrated slfric acid at 1PC reslts in the for,ation of ,ainly trans-&-btene% According to these reslts/ which of the following conclsions ,ight be !alid? A) he reaction ndergoes an &-type eli,ination ,echanis, B) he reaction follows a new ,echanis, in!ol!ing the for,ation of a carbanion inter,ediate C) he reaction ndergoes an 1-type eli,ination ,echanis, in connction with a hydride shift D) he reaction ndergoes an &-type eli,ination ,echanis, in connction with a ,ethyl shift ) he reaction ndergoes an 1-type eli,ination ,echanis, with no shifting Answer" C Diff" ( #ection" $%15 55) What is Taitse!s rle? Answer" 7n eli,ination reactions/ the ,ost highly sbstitted alkene prodct is the ,aor prodct% Diff" & #ection" $%15
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56) 'ow ,any distinct alkene prodcts are possible when the alkyl iodide below ndergoes & eli,ination?
A) 1 B) & C) ( D) ) 3 Answer" Diff" & #ection" $%16 6) Which of the following alkyl halides can prodce only a single alkene prodct fro, when treated with sodi, ,etho4ide? A) &-chloro-&-,ethylpentane B) (-chloro-(-ethylpentane C) (-chloro-&-,ethylpentane D) &-chloro--,ethylpentane ) &-chloro-(-ethylpentane Answer" B Diff" & #ection" $%16 61) 'ow ,any distinct alkene prodcts reslts when 1 -bro,o-1-ethylcyclopenatne is treated with a*C'(? A) 1 B) & C) ( D) Answer" B Diff" & #ection" $%16
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6&) 9ro!ide a strctre for the ,aor sbstittion and ,aor eli,ination prodct reslting fro, the reaction below%
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Diff" & #ection" $%16 6() 9ro!ide the strctre of the ,aor alkene prodct of the reaction below%
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Diff" & #ection" $%16 6) 9ro!ide the ,aor organic prodct of the reaction below%
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Diff" & #ection" $%16
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63) 9ro!ide a series of synthetic steps by which .C'()&CC'& cold be prepared fro, &,ethylpropane% Answer" 1% Br &/ hU &% a*C'(/ C'(*' Diff" & #ection" $%16 6$) 9ro!ide the strctre of the ,aor organic prodct which reslts when &-bro,o-&,ethylbtane is treated with sodi, etho4ide% Answer"
Diff" & #ection" $%16 60) When 1-iodo-1-,ethylcyclohe4ane is treated with a*C'&C'(/ the ,ore highly sbstitted alkene prodct predo,inates% When K*C.C'()(% is sed instead/ the less highly sbstitted alkene prodct predo,inates% *ffer an e4planation% Answer" he nhindered etho4ide procedres the ,ore stable alkene prodct .ie/ the ,ore highly sbstitted alkene possible)% When the blky t -bto4ide is sed/ the ,ost accessible hydrogen is re,o!ed% his reslts in the least highly sbstitted alkene possible% Diff" ( #ection" $%16
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65) When .cis)-1-bro,o-& ,ethylcyclohe4ane is treated with ,ethanol and heat/ for different prodcts are for,ed - two by sbstittion and two by eli,ination%
Which of the following conditions wold change the otco,e of this reaction by pro,oting the prodction of (-,ethylhe4ene as the ,aor prodct?
A) K*'/ ethanol and heat B) waterMacetone and heat C) tert-bto4ideMtert-btyl alcohol D) tert-btyl alcohol and heat ) ,etho4ideM,ethanol Answer" C Diff" ( #ection" $%& 66) 9ro!ide the ,aor organic prodct of the reaction below%
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1) 9ro!ide the strctre of the ,aor organic prodct which reslts in the following reaction%
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Diff" & #ection" $%& 11) 9ro!ide the strctre of the ,aor organic prodct which reslts in the following reaction%
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Diff" & #ection" $%& 1&) 9ro!ide the strctre of the ,aor organic prodct which reslts in the following reaction%
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1() 9ro!ide the strctre of the ,aor organic prodct which reslts in the following reaction%
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Diff" ( #ection" $%& 1) Which diastereo,er of 1-bro,o--t -btylcyclohe4ane/ the cis or the trans/ ndergoes eli,ination ,ore rapidly when treated with sodi, etho4ide? 4plain yor answer% Answer" he cis iso,er reacts ,ore Jickly% An a4ial orientation of the C-Br bond is reJired for & in si4-,e,bered ring syste,s% 7n order for this to occr in the trans iso,er/ the blky t -btyl grop ,st also ass,e an a4ial orientation; this reJires sbstantial energy of acti!ation% Diff" ( #ection" $%& 13) 9ro!ide the strctre of the ,aor organic prodct in the following reaction%
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Diff" ( #ection" $%&
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1$) 9ro!ide the strctre of the ,aor organic prodct in the following reaction%
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Diff" ( #ection" $%& 10) Which of the following ,echanis,s .# 1/ # &/ 1/ &) featre.s) a carbocation inter,ediate? A) # 1 only B) # & only C) 1 only D) & only ) both # 1 and 1 Answer" Diff" 1 #ection" $%&1 15) 7n which of the following ,echanis,s .# 1/ # &/ 1/ &) are alkenes the ,aor reaction prodcts? A) # 1 only B) # & only C) 1 only D) & only ) both 1 and & Answer" Diff" 1 #ection" $%&1
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16) 9redict the ,ost likely ,echanis, for the reaction shown below%
A) # 1 B) # & C) 1 D) & ) 1cb Answer" A Diff" & #ection" $%&1 11) 9redict the ,ost likely ,echanis, for the reaction shown below%
A) # 1 B) # & C) 1 D) & ) 1cb Answer" D Diff" & #ection" $%&1 111) 9redict the two ,ost likely ,echanis,s for the reaction of &-iodohe4ane with sodi, etho4ide% A) # & and # 1 B) 1 and & C) # & and & D) 1 and # 1 ) & and # 1 Answer" C Diff" & #ection" $%&1
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11&) 9redict the two ,ost likely ,echanis,s which occr when &-iodohe4ane is heated in ethanol% A) # & and # 1 B) 1 and & C) # & and & D) 1 and # 1 ) & and # 1 Answer" D Diff" & #ection" $%&1 11() he ,aor prodct fro, the reaction of &-chloro-&-,ethylpentane with sodi, etho4ide in ethanol reslts fro, which of the following ,echanistic pathways? A) # 1 B) # & C) 1 D) & ) 1cb Answer" D Diff" & #ection" $%&1 11) he ,aor prodct which reslts when &-chloro-&-,ethylpentane is heated in ethanol is an ether%
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