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Answer Key
Multiple Choice
l a ,2 d ,3d, 4c , 5d, 6c , 7d , 8 a ,9 d , l 0 a , l 7 b , l 2 e , l 3 d , l 4 a,15a,16a,17e
Short Answer
1. Use the information in the table below to answerthe following question.
l, 3 diaxialinteraction 3.8kJ/mol CH: <+ H H<+H eclipsed 4.0kJ/mol H <+ CHr eclipsed 6.0kJ/mol CHr <+ CH: eclipsed gauche CHr <> CHs Consider the following two compounds: d;ntlrt' tr ans lcyclohexane - 1,2-dimethy cl cl oA l t e^t 1,4-dimethylcyclohexane , + - u r r r l s l r l yr u Ju r u r r s^ d r s crsu rJ- I c7clile4 C l q rq?x 141 Drawthemoststable conformation of each molecule.Usethedatain thetableabove to calculate thetotalstrain energy of each structure.Indicate which, if either,is morestable, andcalculate the energy difference between the two structures.
li?iill, @r-t,z'
4-t,.t-/,k4/-
fra4
N0 rr erAoLv
CtJt
DE=7.6^3.6 t-t )
/l
ans: 3-(iodomethyl)-2-isopropyll-pentanol
3.
CompoundA, C7H1a, was found to be optically active. On catalyticreductionover a palladium catalyst,one equivalentof hydrogen gas was absorbed,yielding optically active compound B, C7H16.When compound A was treated with KMnOa in an acidic solution, CO2bubbled out and compound C was formed. Compound C has the formula C5,H'2O, and it is an optically active ketone. Draw the strucfuresof compounds A, B, and C.
C o
-\--
Reactions
l. below: products resulting ,rdf rn" reaction Draw all possible
2.
ry #-=X
I -,^-t. OHt,T#F 4 Hro.ptl:cHclr' KoH > trans-2-butene
+,-X
ln
I 2-{
"r'
3.
Ol ut
neaf,
l. Hg(OAc)2, H2O/THF
5.
2. NaBH4
/---n
A\tt->
l. osoa
2. NaHSo3. H2o
OH
--;-'
Hro4
G'tto 0
{.
lJ
v'
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.r/
0tl
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8b
9.
Hr!
6" 14
et{er
O
5 0CIz
yzyr;di"e
P4., gile_ GN
,n'
Alo"
cH2oH
ccl4
(9-
G-
Mechanism
I. When3-methylcyclohexene reacts with HCI in ether, oneof theproducts is l-chloro1-methylcyclohexane. Showthecomplete mechanism for the formationof this productusingthe curvedarrowformalism.
ctlt
6+ 6^
_,
*ll
./J
-H
-tl
H
-t
'ct-
2.
\\
Synthesis
l. acetyleneas your only sourceofcarbon 111 > 3-methyl-3-pentanol
,lp^.*ing
*it4
I qrbo^
'Ti
"r;tA
Fo.-^l{ely/e
I
/\-r/ '
lna
')
etle.
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frr-
tr
et/en \ ^-Yl_u,
l-bromobutane-b
2-hexanol
/\.)
4.
ft. l
'# /\/
r rr a
o
t\ cytLt, etlQ7 ) Hto *
a 6n'2"'ntt f ry '*Art "'/h"/h/^/t ,^// /-"''^ hi/:-*"o ^i'a o kthd t ya o"7oa'h'4'/' (?_ t?2.go-, .g t\ cHolcHrPrAe9 /'.) ,J
f/^e. z) )1$+
5. l-butanol ??? > butanal
2-methyl-2-hexanol
OH
?9
Cl1rc1.
/\,/
''-)t
6.
l-butanol
t'!
> butanoicacid
,J
7. cyclohexane
't?1
Cr 0t
tL 0t,acefone
-)
a-,\on
dl
ut e
---
Kn^01\
> cyclohexanone
6.
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o
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U "/t&t?tn
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f-gn,
-c14-4LaeQ---'n--]:&44,/
5{p2 - f-
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tt
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oH C t73c1/z( - c,%_4_ l
nr/
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