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First Exam CHEM 256 – Organic Chemistry II
Prof. Bastin Spring 2013
Name ___________________________ Provide clear, concise answers using unambiquous, carefully drawn structures (where appropriate) for all of the questions. Good luck and enjoy!
1) _______/10 pts 2) _______/10 pts
3) _______/12 pts
4) _______/12 pts Total: ________/100 pts 5) _______/8 pts
6) _______/20 pts
7) _______/10 pts 8) _______/8 pts 9) _______/10 pts
Bastin – Exam #1 Chem 256 - Spring 2013
2
1) (10 pts) Provide structures for the following compounds.
(a) 2,3-diethoxybutane (b) sec-butyl alcohol
(c) cis-2-ethylcyclobutanol (d) (2S, 3S)-3-ethoxy-2-pentanol (e) butyl hexyl ether
Bastin – Exam #1 Chem 256 - Spring 2013
3
2) (10 pts) Provide either common or IUPAC names for the following compounds. (a) (b)
(c) (d)
(e)
H OH
O
OCH2CH3
OH
Cl OH
O
OH
Bastin – Exam #1 Chem 256 - Spring 2013
4
3) (12 pts) Draw the product(s), if any, of the following reactions. Indicate stereochemistry where relevant.
a)
b)
c)
d)
e)
f)
OH polymer-supported CrO3Toluene
OH 1)TsCl2) NaI
O
CH3
NaSHH2O
OH
OH
HIO4
OH2 H2SO4Δ
1) Br2/H2O2) NaOH
Bastin – Exam #1 Chem 256 - Spring 2013
5
4) (12 pts) Provide the reagents needed to bring about the following transformations.
a)
b)
(c)
(d)
(e)
(f)
OOH
H3CH2C CH3
H3CH2CH2COH
H3CH2C CH3
H3CH2CH2COH
O
OOH
OCH2CH3
OHH
O
O
Br
Br
+
OH Br
Bastin – Exam #1 Chem 256 - Spring 2013
6
5) (8 pts) Assume you are carrying out the oxidation shown below. How could you use IR spectroscopy to determine when the reaction is complete? Provide as many different analyses you can think of.
6) (20 pts) Devise (on the following blank page) a synthesis for the following
transformations using any reagents that we have discussed. If you need more space, please ask and I will provide you with an additional sheet of paper. For FULL credit be sure to show the retrosynthetic analysis AND the complete synthesis.
a)
b)
H
O
OH
O
[O]
O
OH
from
Cl
and
These molecules are your only source of carbon
from OH
This molecule is your only source of carbon
Bastin – Exam #1 Chem 256 - Spring 2013
7
Bastin – Exam #1 Chem 256 - Spring 2013
8
7) (10 pts) For each of the following IR spectra (a-e) there is a choice of three possible types of compounds. For each spectrum, choose the most appropriate class of compound. Explain your reasoning by noting the presence or absence of characteristic bands in the spectrum.
a) alcohol, carboxylic acid, or phenol
b) aldehyde, ester, or ketone
c) 1-alkyne, symmetrical internal alkyne, or nitrile
PR0BLEM 15.34 (C0lrTrr{UED).l Microns (F)
22 2.12.A2.A 3 3,5 44,5 5 5.5 0 7 I 910 11 12131a15t0lEm225
AlcoholCarboryllc acldPhenol
a 2.6 2.8 3 3.5 a 4.5
2 AldehydeEsterKetone2.2 2,4 2,4 2,4 3 3.5 4 4.5
Microns 0r)5 5.5 6 7 8 I10 t l 1?!3 l4t5r6.r l t | i
Microns 0r)5 5.6 6 7 6 I t0 1t 12t14r5r! 'a
so
o
EE 1psoEF2@ ru@1@1@r@iA1@
Wavenumb€r (cml )
Mims0)3.5 . .5 5 55 6 7 S 910
& m m 20 rum1&10101rurm & Gwsvonumber (crr1)
ao
c
E
IF2
Eo6
c
sF
oo
o
so
E6qt
21 2.4 2.E 3 11 12 13 1a 1510 11 82 25
s re & @&1@1@ro1&1@Wavsnumber (cm-l)
Microns (p)5678910111213!415r8
@ re m mmrsrorolrur@Wavmumb€r (cml)
3 l-AlkyneSymmetrlcal dlsubstltuted alkyneGyanide Mtcrons (r)22 2t 2.e2.4 3 3.5 I 1.5 5 5.5 6 7 8 I 10
4-
silf*-\ f-T-\rrn n*,d1lt11 12 13 ta 15.a r
FogsE0po.Ee4
8a
EoEF
Microns 0422 2.4232.6 3 3.5 44.5 5 5.5 6 7 8 9r0 f i 12131a1514r8n25
w 2m 2mm1&1m1&1mtmWavenumbor (cml)
Micmns (p)22 2.42.62.8 3 3-5 a4.5 5 5.56 7 E 910 11 12131ar5r61E626
@ @ m 2m ro@rmlm101&1@Wavonumbs (cr1)
4 Primary amidePrimary amineNitro compound
1 2.6 2.8 g 3.3 a a.!Microns (F)
5.5 6 7 a 910 11 12 13 r . r l t I
@oo
EF
*-v*2& 2mro1&tmr@!ru1s
Wavonumbsr (cm-1)
PR0BIEM 15.35 For each of the following lR spectra (1-5)there is a choice of three possible types of compounds. Foreach spectrum, choose the most appropriate class of com-pound. Explain your reasoning by noting the presence or ab-sence of characteristic bands in the soectrum.
@ @ ru 2m m@1m1@1@1m1@Wav€numbs (cr1)
5 AnhydrideGarboxylic acidEster Microns (d2.2 2.42.82.5 3 3.5 44.5 5 5.5 6 7 I 910 11 12131. ' ! ! .
@ @ ru 2m ru@rmr&tolru1mWav6numb6r (cm1)
0.0q601 >0.2803Ao.r P0.5 60.6 0
1.02.0
rf1ms&70@s{s10
Wav€number (crn-l)
PR0BLEM 15.34 (C0lrTrr{UED).l Microns (F)
22 2.12.A2.A 3 3,5 44,5 5 5.5 0 7 I 910 11 12131a15t0lEm225
AlcoholCarboryllc acldPhenol
a 2.6 2.8 3 3.5 a 4.5
2 AldehydeEsterKetone2.2 2,4 2,4 2,4 3 3.5 4 4.5
Microns 0r)5 5.5 6 7 8 I10 t l 1?!3 l4t5r6.r l t | i
Microns 0r)5 5.6 6 7 6 I t0 1t 12t14r5r! 'a
so
o
EE 1psoEF2@ ru@1@1@r@iA1@
Wavenumb€r (cml )
Mims0)3.5 . .5 5 55 6 7 S 910
& m m 20 rum1&10101rurm & Gwsvonumber (crr1)
ao
c
E
IF2
Eo6
c
sF
oo
o
so
E6qt
21 2.4 2.E 3 11 12 13 1a 1510 11 82 25
s re & @&1@1@ro1&1@Wavsnumber (cm-l)
Microns (p)5678910111213!415r8
@ re m mmrsrorolrur@Wavmumb€r (cml)
3 l-AlkyneSymmetrlcal dlsubstltuted alkyneGyanide Mtcrons (r)22 2t 2.e2.4 3 3.5 I 1.5 5 5.5 6 7 8 I 10
4-
silf*-\ f-T-\rrn n*,d1lt11 12 13 ta 15.a r
FogsE0po.Ee4
8a
EoEF
Microns 0422 2.4232.6 3 3.5 44.5 5 5.5 6 7 8 9r0 f i 12131a1514r8n25
w 2m 2mm1&1m1&1mtmWavenumbor (cml)
Micmns (p)22 2.42.62.8 3 3-5 a4.5 5 5.56 7 E 910 11 12131ar5r61E626
@ @ m 2m ro@rmlm101&1@Wavonumbs (cr1)
4 Primary amidePrimary amineNitro compound
1 2.6 2.8 g 3.3 a a.!Microns (F)
5.5 6 7 a 910 11 12 13 r . r l t I
@oo
EF
*-v*2& 2mro1&tmr@!ru1s
Wavonumbsr (cm-1)
PR0BIEM 15.35 For each of the following lR spectra (1-5)there is a choice of three possible types of compounds. Foreach spectrum, choose the most appropriate class of com-pound. Explain your reasoning by noting the presence or ab-sence of characteristic bands in the soectrum.
@ @ ru 2m m@1m1@1@1m1@Wav€numbs (cr1)
5 AnhydrideGarboxylic acidEster Microns (d2.2 2.42.82.5 3 3.5 44.5 5 5.5 6 7 I 910 11 12131. ' ! ! .
@ @ ru 2m ru@rmr&tolru1mWav6numb6r (cm1)
0.0q601 >0.2803Ao.r P0.5 60.6 0
1.02.0
rf1ms&70@s{s10
Wav€number (crn-l)
PR0BLEM 15.34 (C0lrTrr{UED).l Microns (F)
22 2.12.A2.A 3 3,5 44,5 5 5.5 0 7 I 910 11 12131a15t0lEm225
AlcoholCarboryllc acldPhenol
a 2.6 2.8 3 3.5 a 4.5
2 AldehydeEsterKetone2.2 2,4 2,4 2,4 3 3.5 4 4.5
Microns 0r)5 5.5 6 7 8 I10 t l 1?!3 l4t5r6.r l t | i
Microns 0r)5 5.6 6 7 6 I t0 1t 12t14r5r! 'a
so
o
EE 1psoEF2@ ru@1@1@r@iA1@
Wavenumb€r (cml )
Mims0)3.5 . .5 5 55 6 7 S 910
& m m 20 rum1&10101rurm & Gwsvonumber (crr1)
ao
c
E
IF2
Eo6
c
sF
oo
o
so
E6qt
21 2.4 2.E 3 11 12 13 1a 1510 11 82 25
s re & @&1@1@ro1&1@Wavsnumber (cm-l)
Microns (p)5678910111213!415r8
@ re m mmrsrorolrur@Wavmumb€r (cml)
3 l-AlkyneSymmetrlcal dlsubstltuted alkyneGyanide Mtcrons (r)22 2t 2.e2.4 3 3.5 I 1.5 5 5.5 6 7 8 I 10
4-
silf*-\ f-T-\rrn n*,d1lt11 12 13 ta 15.a r
FogsE0po.Ee4
8a
EoEF
Microns 0422 2.4232.6 3 3.5 44.5 5 5.5 6 7 8 9r0 f i 12131a1514r8n25
w 2m 2mm1&1m1&1mtmWavenumbor (cml)
Micmns (p)22 2.42.62.8 3 3-5 a4.5 5 5.56 7 E 910 11 12131ar5r61E626
@ @ m 2m ro@rmlm101&1@Wavonumbs (cr1)
4 Primary amidePrimary amineNitro compound
1 2.6 2.8 g 3.3 a a.!Microns (F)
5.5 6 7 a 910 11 12 13 r . r l t I
@oo
EF
*-v*2& 2mro1&tmr@!ru1s
Wavonumbsr (cm-1)
PR0BIEM 15.35 For each of the following lR spectra (1-5)there is a choice of three possible types of compounds. Foreach spectrum, choose the most appropriate class of com-pound. Explain your reasoning by noting the presence or ab-sence of characteristic bands in the soectrum.
@ @ ru 2m m@1m1@1@1m1@Wav€numbs (cr1)
5 AnhydrideGarboxylic acidEster Microns (d2.2 2.42.82.5 3 3.5 44.5 5 5.5 6 7 I 910 11 12131. ' ! ! .
@ @ ru 2m ru@rmr&tolru1mWav6numb6r (cm1)
0.0q601 >0.2803Ao.r P0.5 60.6 0
1.02.0
rf1ms&70@s{s10
Wav€number (crn-l)
Bastin – Exam #1 Chem 256 - Spring 2013
9
d) primary amide, primary amine, or nitro compound
e) anhydride, carboxylic acid, or ester
PR0BLEM 15.34 (C0lrTrr{UED).l Microns (F)
22 2.12.A2.A 3 3,5 44,5 5 5.5 0 7 I 910 11 12131a15t0lEm225
AlcoholCarboryllc acldPhenol
a 2.6 2.8 3 3.5 a 4.5
2 AldehydeEsterKetone2.2 2,4 2,4 2,4 3 3.5 4 4.5
Microns 0r)5 5.5 6 7 8 I10 t l 1?!3 l4t5r6.r l t | i
Microns 0r)5 5.6 6 7 6 I t0 1t 12t14r5r! 'a
so
o
EE 1psoEF2@ ru@1@1@r@iA1@
Wavenumb€r (cml )
Mims0)3.5 . .5 5 55 6 7 S 910
& m m 20 rum1&10101rurm & Gwsvonumber (crr1)
ao
c
E
IF2
Eo6
c
sF
oo
o
so
E6qt
21 2.4 2.E 3 11 12 13 1a 1510 11 82 25
s re & @&1@1@ro1&1@Wavsnumber (cm-l)
Microns (p)5678910111213!415r8
@ re m mmrsrorolrur@Wavmumb€r (cml)
3 l-AlkyneSymmetrlcal dlsubstltuted alkyneGyanide Mtcrons (r)22 2t 2.e2.4 3 3.5 I 1.5 5 5.5 6 7 8 I 10
4-
silf*-\ f-T-\rrn n*,d1lt11 12 13 ta 15.a r
FogsE0po.Ee4
8a
EoEF
Microns 0422 2.4232.6 3 3.5 44.5 5 5.5 6 7 8 9r0 f i 12131a1514r8n25
w 2m 2mm1&1m1&1mtmWavenumbor (cml)
Micmns (p)22 2.42.62.8 3 3-5 a4.5 5 5.56 7 E 910 11 12131ar5r61E626
@ @ m 2m ro@rmlm101&1@Wavonumbs (cr1)
4 Primary amidePrimary amineNitro compound
1 2.6 2.8 g 3.3 a a.!Microns (F)
5.5 6 7 a 910 11 12 13 r . r l t I
@oo
EF
*-v*2& 2mro1&tmr@!ru1s
Wavonumbsr (cm-1)
PR0BIEM 15.35 For each of the following lR spectra (1-5)there is a choice of three possible types of compounds. Foreach spectrum, choose the most appropriate class of com-pound. Explain your reasoning by noting the presence or ab-sence of characteristic bands in the soectrum.
@ @ ru 2m m@1m1@1@1m1@Wav€numbs (cr1)
5 AnhydrideGarboxylic acidEster Microns (d2.2 2.42.82.5 3 3.5 44.5 5 5.5 6 7 I 910 11 12131. ' ! ! .
@ @ ru 2m ru@rmr&tolru1mWav6numb6r (cm1)
0.0q601 >0.2803Ao.r P0.5 60.6 0
1.02.0
rf1ms&70@s{s10
Wav€number (crn-l)
PR0BLEM 15.34 (C0lrTrr{UED).l Microns (F)
22 2.12.A2.A 3 3,5 44,5 5 5.5 0 7 I 910 11 12131a15t0lEm225
AlcoholCarboryllc acldPhenol
a 2.6 2.8 3 3.5 a 4.5
2 AldehydeEsterKetone2.2 2,4 2,4 2,4 3 3.5 4 4.5
Microns 0r)5 5.5 6 7 8 I10 t l 1?!3 l4t5r6.r l t | i
Microns 0r)5 5.6 6 7 6 I t0 1t 12t14r5r! 'a
so
o
EE 1psoEF2@ ru@1@1@r@iA1@
Wavenumb€r (cml )
Mims0)3.5 . .5 5 55 6 7 S 910
& m m 20 rum1&10101rurm & Gwsvonumber (crr1)
ao
c
E
IF2
Eo6
c
sF
oo
o
so
E6qt
21 2.4 2.E 3 11 12 13 1a 1510 11 82 25
s re & @&1@1@ro1&1@Wavsnumber (cm-l)
Microns (p)5678910111213!415r8
@ re m mmrsrorolrur@Wavmumb€r (cml)
3 l-AlkyneSymmetrlcal dlsubstltuted alkyneGyanide Mtcrons (r)22 2t 2.e2.4 3 3.5 I 1.5 5 5.5 6 7 8 I 10
4-
silf*-\ f-T-\rrn n*,d1lt11 12 13 ta 15.a r
FogsE0po.Ee4
8a
EoEF
Microns 0422 2.4232.6 3 3.5 44.5 5 5.5 6 7 8 9r0 f i 12131a1514r8n25
w 2m 2mm1&1m1&1mtmWavenumbor (cml)
Micmns (p)22 2.42.62.8 3 3-5 a4.5 5 5.56 7 E 910 11 12131ar5r61E626
@ @ m 2m ro@rmlm101&1@Wavonumbs (cr1)
4 Primary amidePrimary amineNitro compound
1 2.6 2.8 g 3.3 a a.!Microns (F)
5.5 6 7 a 910 11 12 13 r . r l t I
@oo
EF
*-v*2& 2mro1&tmr@!ru1s
Wavonumbsr (cm-1)
PR0BIEM 15.35 For each of the following lR spectra (1-5)there is a choice of three possible types of compounds. Foreach spectrum, choose the most appropriate class of com-pound. Explain your reasoning by noting the presence or ab-sence of characteristic bands in the soectrum.
@ @ ru 2m m@1m1@1@1m1@Wav€numbs (cr1)
5 AnhydrideGarboxylic acidEster Microns (d2.2 2.42.82.5 3 3.5 44.5 5 5.5 6 7 I 910 11 12131. ' ! ! .
@ @ ru 2m ru@rmr&tolru1mWav6numb6r (cm1)
0.0q601 >0.2803Ao.r P0.5 60.6 0
1.02.0
rf1ms&70@s{s10
Wav€number (crn-l)
Bastin – Exam #1 Chem 256 - Spring 2013
10
8) (8 pts) Provide a mechanistic explanation for the following reaction. Be sure to explain the regioselectivity of the reaction.
CH3CH2OHH+
OCH2CH3
Bastin – Exam #1 Chem 256 - Spring 2013
11
9) (10 pts) Two diasteromeric sets of enantiomers, A/B and C/D, exist for 3-bromo-2-butanol.
When enantiomer A or B is treated with HBr, only racemic 2,3-dibromobutane is formed; NO meso isomer is formed. When enantiomer C or D is treated with HBr, only meso-2,3-dibromobutane is formed; NO racemic 2,3-dibromobutane is formed. Account for these observations using the reaction mechanism.
CH3
HHO
BrH
CH3
CH3
OHH
HBr
CH3
CH3
OHH
BrH
CH3
CH3
HHO
HBr
CH3
A B C D
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