NAME: _______________________

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Please put the answers to the multiple choice questions on an scantron (Form # 882)
2! Multiple "hoice #s $ % pt each----- &hort Answers '( pts Total = 55 points
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% )hich o* the *ollowin+ is the correct ,-PA" name *or the *ollowin+ compoun./

a %-meth0l-2-c0clohe1ene 2 2-meth0lc0clohe1ene
c '-meth0lc0clohe1ene . %-meth0l-(-c0clohe1ene
2 )hich o* the *ollowin+ is the correct ,-PA" name *or the *ollowin+ compoun./

a 2-eth0l-%3%3'-trimeth0l2utene 2 '-eth0l-234-.imeth0l-2-pentene
c 234-.imeth0lhe1ene . 4-eth0l-%3'-.imeth0l-'-pentene
' ,n an a..ition reaction to an al5ene3 the .ou2le 2on. pla0s the role o*:
a nucleophile 2 electrophile c lea6in+ +roup
. A an. 7 e 7 an. "
4 )hich o* the molecules 2elow woul. 2e the e1pecte. pro.uct *or h0.rohalo+enation o* the
*ollowin+ al5ene:

a 2 c
. e
( 8he e1pecte. Mar5o6ni5o6 a..ition pro.uct o* 9, to 2-meth0l-2-2utene is:
a 2-io.opentane 2 2-io.o-2-meth0l2utane
c %-io.o-2-meth0l2utane . 2-io.o-%-meth0l2utane
e '-io.o-2-meth0l2utane
: )hich o* the structures shown .epicts the most sta2le car2ocation interme.iate *orme. in a
h0.rohalo+enation reaction/

a , 2 ,, c ,,, . ,; e ;
< 8he e1pecte. major pro.uct o* the *ollowin+ reaction is:

a 2 c
. e
8 )hich o* the molecules 2elow is pro.uce. *rom h0.rohalo+enation o* the c0cloal5ene shown
with 97r/

a 2 c
. e
= )hat is the ,-PA" name o* the e1pecte. major pro.uct *orme. upon reaction o* 9"l with '-
meth0l-%-2utene/
a %-"hloro-2-meth0l2utane 2 %-"hloro-'-meth0l2utane
c 2-"hloro-2-meth0l2utane . 2-"hloro-'-meth0l2utane
e %-"hloropentane
%! )hat pro.uct is *orme. when (-chloro-%-meth0lc0clohe1ene is re.uce. with a Pt catal0st an.
9
2
/
a %-chloro-(-meth0lc0clohe1ane 2 %-chloro-'-meth0lc0clohe1ane
c (-chloro-%-meth0lc0clohe1ane . '-chloro-%-meth0lc0clohe1ane
%% 8reatin+ 2-meth0l-2-pentene with 7r
2
is e1pecte. to pro.uce which o* the *ollowin+ as the
major pro.uct/
a 23'-.i2romo-2-meth0lpentane 2 232-.i2romo-2-meth0lpentane
c '3'-.i2romo-2-meth0lpentane . 2-2romo-2-meth0lpentane
e '-.i2romo-2-meth0lpentane
%2 )hich o* *ollowin+ statements 2est .escri2es the +eneral reacti6it0 o* al50nes/
a An al50ne reacts as a nucleophile3 an. is there*ore electron rich
2 An al50ne reacts as a nucleophile3 an. is there*ore electron poor
c Al50nes *ail to un.er+o a..ition reactions3 unli5e al5enes
. An al50ne reacts as an electrophile3 an. is there*ore electron rich
e An al50ne reacts as an electrophile3 an. is there*ore electron poor
%' )hat is the correct ,-PA" name *or the molecule shown 2elow/

a 2-Meth0l-(-prop0l-'-hept0ne 2 (-Eth0l-2-meth0l-'-oct0ne
c %-,soprop0l-'-eth0l-%-he10ne . :-Meth0l-'-prop0l-4-hept0ne
e 4-Eth0l-<-meth0l-(-oct0ne
%4 )hat is the correct ,-PA" name *or the molecule shown 2elow/

a (3:3:-8rimeth0l-%-hept0ne 2 (-tert-8ut0l-%-he10ne
c 2323'-8rimeth0l-:-hept0ne . 2323'-('-7ut0n0l)2utane
%( )hich o* the *ollowin+ is the correct structure *or '-sec-2ut0l-%-hept0ne/

a , 2 ,, c ,,, . ,; e ;
%: For the reaction shown3 select the ma>or pro.uct

a , 2 ,, c ,,, . ,; e ;
%< "omplete h0.ro+enation o* a mi1ture o* %-oct0ne3 2-oct0ne3 an. '-oct0ne3 in the presence o*
a metal catal0st3 woul. pro.uce how man0 .istinct ei+ht-car2on h0.rocar2on pro.ucts/
a % 2 2 c ' . : e 8
%8 )hich o* the compoun.s shown 2elow woul. 2e the pro.uct e1pecte. *rom the reaction
scheme shown/

a , 2 ,, c ,,, . ,; e ;
%= )hat is the correct structure *or 4-amino-2-chlorophenol/

a , 2 ,, c ,,, . ,; e ;
2! )hat is the ,-PA" name *or the *ollowin+ compoun./


a '34-.ichloroaniline
2 234-.ichloroaniline
c 23(-.ichloroaniline
. '3:-.ichloroaniline
e 23:-.ichloroaniline
Short Answers
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Pro2 # % (%2 pts) Pro6i.e an ,-PA" name *or each o* the *ollowin+ compoun.s
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"9
'
"("9
'
)
2
"9
2
"?""9
2
"9("9
2
"9
'
)"9
' _____________________________________
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Pro2 # 2 (: pts): @raw the 2on. line structure o* each compoun.
(a) 23'-.imeth0l-%-pentene
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(2) trans-2-meth0l-'-heptene ___________________________________
(c) cis-'34-.imeth0l-'-he1ene ___________________________________
Pro2 # ' (: pts): Pre.ict (.raw the structure) the pro.uct o* each reaction


Pro2 # 4 (: pts): Pro6i.e the rea+ents necessar0 (above the two arrows) an. the interme.iate
structure (left blank between the two arrows) in the *ollowin+ two-step reaction sequence

7r
&A
'
9
Pro2 # ( (( pts): Propose a three-step curved arrow reaction mechanism *or the aci.-catal0Be.
h0.ration o* 2-meth0l-2-2utene