Download Exam 3 -Key - SUNY Oneonta

Name:
ftci srnfZe V:ei
Exam 3, May 1,2013
CHEM 226 -Elementary Organic Chemistry
SUNY ONEONTA
Spring 2013
Attempt all questions within the spaces provided shou,ing your stelts clearly.for partial credit. Enter your
answers for questions I I-23 in the table provided on page 2
1.
Which reagents would be besi for reaction sequence to synthesize p-bromobenzenesulfonic acid from
benzene?
r
r'
5O3H
J.
l)
ra)
A" So3 i
(]]
2)
\71tI
3.
r,&* ' O.E-5>
0
i"€-
d,..e- l*
Cr\rqe*
ol-der'
Draw the structure of the compound produced tiom the following reaction?
CI
(8\
bl-S 04
Jln"<e* rxns h^r.- {o
Br
2.
Br- / Fe Br 3
+ Hc\
(+)
What reagents would accomplish the following transformation?
,f
cH2cHzoH
il
P
CL
€t4z4z-
4.
('I
\.)
I
l{aNH?
/F-\
z ft \\--i:H.e.
\*/
qr{
->
-l
-+
\.\etflr
* Nt\3t
(e\
1 ! ropcnen€
6\
*lo
.- q'qg
6)
Draw the major product of the fbllowing acid catalyzed dehydration reaction?
'fH
I
v\
- Pra
qcrr*'^z
Ac.jv'"c-
What is the Ka of phenol if its pKa is 9.95?
Ko=
.
s*ct{3
CrlD3
'*t,
7
1$- .*z*c=
What is the structure and name of the compound formed when isopropyl alcohol is treated with Jones'
reagent?
6.
k\
What is the final product of the following sequence of reactiot.ts?
CH3C:CH
5.
r"H^r.H
*.^S*
H25f,ta {catalyst)
prtrrt*'-L
hed
ld^n9" z- L;le'n
\A
tu\
n
o'f
er
p-J*"b
(+\
(Y"u
(Y"'o
NCIi
cv{-'
ff"*
Arrange the fotlowing compounds,"
p-methylphenol
o.#sn"reasing
< Pl'e^J L
p- Xneffix',"ri
9.
o
(;\
(2)
acidity;
,r.""-i
P --t-l-,+''
:fuhenol
and
14)
Phe^*Q
Arrange the following compounds in order of increasing boiling points; dimethyl ether CH3OCH3
(MW: 46), ethanol CH:CHzOH (MW:46), and propane CH:CHzCH: (MW :44).
f'ra pana
d- dt^^"tt"5i e\f'e'rZ
E tt.'',."{
ft)
'
10. Draw the product of the following reaction
-|{'
11.
*
CrO3, H2SOa, acetone
Nc
cixlAizeA
Which bromide will react fastest in Sy2 reactions?
A)
B)
C)
CH:BT
D)
(CH3)2CHBr
E)
(CH3)3CCH2Br
CH:CHZBT
D)
proton acceptor
(CH3) 3CBr
t2. A Lewis base is a:
A) proton donor
B) electron pair donor
C) electron pair acceptor
13.
t c-\.oL,-\s
Y-xn
Phenols are stronger acids than alcohols because ofthe
A) resonance stabilization ofphenoxide ions.
B) resonance stabilization ofphenols.
C) resonance stabilization ofalkoxide ions.
D) resonance stabilization of alcohois.
E) hydrogen bonding in phenols.
t4. What would be the IUPAC name for the following alcohol?
A)
B)
C)
D)
E)
3-
4$
t5Z
'1 e'fal
\PO
5€.h;
"
l3
t1
t2
A
E A
t4
Pet'^'[
4 -"*thd'2-
15
t8
16
t7
A
B b
t9
20
b
A
2t
22
23
b
A
'-
2
Sec*r"
2-methyl-4-pentanol
2-methyl-4-hydroxlpentane
4-methyl-2-pentanol
4-hydroxy-2-methylpentane
2-hydroxy-4-methylpentane
Total score
e D
E
<o^^
6)
* ba
15.
Which of the following molecules is the correct structure for dibenzyl ether?
A)
CH3CH20CH2CH3
B)(}"S
c)
D)
E)
16.
ry"*'
G"*""*C
G"**"S
Which of the following is a Grignard reagent?
A) CH3MgCl
B)
C)
D)
E)
CH:Li
(CH3)2
CuLi
CH:NA
(CH)2Zn
17. Which reaction will yield CH3CH2CH2D?
A) CH3CH2CH3 + D2O
B) CH3CH2CH2MgBT + D2O
C)
D)
' E)
CH3CH2CH2OLi
+
D2O
CHTCH2CH2OH + D2O
more than one of these
t8. Starting with p-bromoanisole (p-bromophenyl methyl ether), whatsequence of reactions will produce
p-deuterioanisole?
*S**
p-bromoarusole
A) l.D2O 2. Br2, AlBr3
B) 1. Mg, ether 2. D2O
C) l. D2O 2. Mg, ether
D) 1. HzSO+, D 2.M9, ether 3. DzO
E) 1. Brz, AlBr:, 2. Mg, ether, 3. D2O
#-
B'*5{}o't+3 -5
D*O-ocFr3
+ mg Br o$-
19. Hydrolysis ofthe disaccharide maltose produces:
A)
B)
C)
D)
E)
sucrose
glucose
mannose
glucose and fructose
glucose and galactose
20. Hydrolysis of lactose gives:
A)
B)
C)
D)
E)
glucose and galactose
glucose and fructose
mannose and fructose
galactose and fructose
allose and mannose
21. The relative rates of nitration of the following are:
H:C
CHe
t-
A)
B)
1>2>3>4
4>2> 1>3
A
V
o
c) 2> 7> 4>3
D)
E)
3>4>2>l
3>2>1>4
22. Which of the following groups is a meta director?
A) -Cl
B) -CooH
c)
D)
E)
-ocH3
-OH
C)
--t
It
_ c-D
g:
l*
rllt q*
-{ttee*rc'c\
-NH2
is reacted with the bulky base, potassium tert-btioxlde, in tert:butyl alcohol,
the major elimination product is:
23. When 1 -bromopentane
A) 1-pentene
B) cls-2-pentene
C) trans-2-pentene
D) buffl rert-butyl ether
E) butyl alcohol
c(3
c
5' l-st
)u.
r.(+)
t-pe*e/€-
nu,^
6*3cH2ck[
1
ttiq*r
l+
*i'
cbchc']acrr=c+z
I lcBr
J-
@t+u)9ort
Good Luck