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Solutions to Exam 2 - Organic Chemistry I | CHE 2201, Exams of Organic Chemistry

Material Type: Exam; Class: ORGANIC CHEMISTRY I; Subject: Chemistry; University: Appalachian State University; Term: Fall 2002;

Typology: Exams

Pre 2010

Uploaded on 08/30/2009

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SI Organic Chemistry Worksheet #6
October 21, 2002
(
c~- I(~
Label the electrophile and the nucleophile, then show the mechanism to form an alkyl
halide. Cr:-J
, (J.- @ \l~ X e 7 ~~
.--x ~ ~- r -~ -(& --7 ctt-G -c:-(lts
E@ ct?, ~ c~ ~
I"
-c=c
~l.( "l ~
t
c~
2.State Markonikov's rule.
\n-tVle ttdtl{~.D\11 ()f- ~ 10 aV) tUKfV\e -tV1f ~ t\.itZ1d1ff .fr> -HIIf. CttvV/OVI .
Vv\.tvl f{ wev Rlk4l \~~1ItlAeMt ~VlA ~t A ~-tta(,nfJ tv itAe ('A vj,:}()~1 lM-tiII
M O~e OJ k.~ I fU.w{1,~(,(11t
.Draw the product formed from thii reactio~
Cl'b ~ ~ @ ~
~( :=:CH2 i H-ci ~ C(~-C ~-tt
C~ C~ ~
3
C{
"
qQ C~-'c --c~
(l-l3
-7
What alkene would you start with to prepare the following alkyl halides1
a) b)
4
~./..::::::-
0j
L
J" .
C[flV
Rank the following in order of increasing stability
(:11 (f) ~~
C~ ~ C~tb.- ~ C~-C~ L.
(£)
+ ttC(
t ti ""Bv -: '-'
5
major product from the addition of HBr to each alkene
I
IV b) I
l ~ /'..,... J
6Predict th{
a)
)
"-./ ~
(~
I
c) (tV.:lt\2l\\:2 ~(~(~
'PJY
pf2

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SI Organic Chemistry Worksheet

October 21, 2002

c~- ( I(~

Label the electrophile and the nucleophile, then show the mechanism to form an alkyl halide. Cr:-J

, (J.- @ \l~ X e 7 ~~

.--x ~ ~- r -~ -(& --7 ctt-G -c:-(lts E@ ct?, ~ c~ ~

I" -c=c ~l.( "l ~

t

c~

2 .State Markonikov's rule. \n-tVle ttdtl{~.D\11 ()f- ~ 10 aV) tUKfV\e -tV1f ~ t.itZ1d1ff .fr> -HIIf. CttvV/OVI. Vv.tvl f{ wev Rlk4l ~~1ItlAeMt ~VlA ~t A ~-tta(,nfJ tv itAe ('A vj,:}()~1 lM-tiII M O~e OJ k.~ I fU.w{1,~(,(11t .Draw the product formed from thii reactio~

Cl'b ~ ~ @ ~ ~( :=:CH2 i H-ci ~ C(~-C ~-tt C~ C~ ~

C{

" qQ

C~-'c --c~

(l-l

What alkene would you start with to prepare the following alkyl halides

a) b)

~./..::::::- (^0) j L J".

C[flV Rank the following in order of increasing stability

(:11 (f) ~~ C~ ~ C~tb.- ~ C~-C~ L. (£)

t ti ""Bv + ttC( -: '-'

I^ major^ product^ from^ the^ addition^ of^ HBr^ to^ each^ alkene IV b) I l ~ /'..,... J

6 Predict th{

a)

"-./ ) ~ (~I c) (tV.:lt\2l\:2 ~(~(~

'PJY

  1. State the Harnmond postulate. 1YIe '7tvut:1\IYe or t:l1rt{;V1~1'11.0V1 s-j1{tt 'reslWlhl(J tYIe ftvu{Jwf' Cf- tlt1( nf()JrfIt

Sft{V}I( sP(Q.eJ, \vf.(lI1~ftioV\ s{l{tej -ro~ eVt~i VU-( ~ s1YUc.tU~tU~ v(I011 ble pvutl(~

6t11\ut ~tU1SI.fi.()V1 s-tlttef -(t'v e)(.ev4°YU( ( ?twtt\1.~LLu ve~V,{wle' D~tiUtfc ~ M()ve s.ta.1?le ca.JtvoCtt(luV\ \ .(Ilr"", -fil~fe¥ blc. 'V.~-\7:{i?tt{t1{ J lJ vttlfC.tfc~ I VI it1e

  1. What IS the purpose ofa hydrIde or f,~-methyl shift? traJIICI'-ti'oY\ s1Zttt lr~(n~ to 1iIIeJ"V

10 ft>lrM. Ct M.Ove S1tL~le CaJ-b{)(t{-h(M

Propose a mechanism for the reaction. If

'--//-.J~ t- ~ -(};>v(Jr^ --t CJ 4t~ ;,."'"ii~-1.(.

H h ~ande ~n(tt

~

(,~

~

.

  1. Propose a mechanism for the reacC~n. ,~ Il ~rd -d~ ~-q ~ O~

It - h4tlMlLt Sttltt"

TEST

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