Cole Chemistry 536/736
Problem Set #2 IR Spectroscopy
September 14, 2022 Due September 21, 2022
Note: Show rational in answering the questions.
1. Shown below is the spectrum of an unknown submitted for infrared analysis. The compound is
suspected to be one of the following compounds:
CH3 CH3 Cl Cl
✗ ✗
Cl
ortho
para
Cl Cl Cl
r ti
W
substituted
' Cpana)
Sp /
carbons
oh }
sp3
Methyl
C- Cl
stretch
para
ill
!
No ortho
?⃝
?⃝
° Primary or Secondary
6×2 1-2-14
=
Alcohol
\
2. A liquid unknown was found to have a molecular formula of C6H14O. This compound reacted rapidly
* Secondarywith chromic acid (H2CrO4 – oxidant) to give a blue-green ppt. This compound also gave positive iodoform
alcohol test. These latter two pieces of information give additional reaction information. Propose a structure for this
unknown and show rational to support your answer.
-
on
I /
I
No
1
CHZ
Carbonyl
stretch
⊖
-
propyl
* C. • Hino
* Reacts with chromic Acid for 2° Alcohol OH
, so
* Positive iodoform test means Ethanol ~ on
or methyl secondary alcohol
"
at 3350cm
* -
OH peak
-1
before 3000cm
* Alkane peaks
"
peak at 1450cm
* cuz
' '
at 1380cm
* propyl peak
Cs
3. A liquid unknown compound has a boiling point of 69-70 °C. The elemental analysis give a composition of
87.64% C and 12.36 % H. This compound readily reacts with both Br2 in carbon tetrachloride and with
oxidizes
-
KMnO4. The IR spectra is shown as a neat film is shown below. Propose a structure that is consistent with the
_
with provided data.
alkenes /
alkynes
CEC
0 ① CH}
=C H -
* 87--64--1 Cs H to
100's ×
✗ = 82 .
-7%5=10 H "
* We have = c- H stretch peak at 3300cm
an
* 69 -70°C resembles a 6 carbon alkane chain
"
show triple bond between 2 carbons
* Peak at 2100cm
a
H
'
H
Sp Carbons
" H
show that there are
many µ
before 3000cm , ,
.
* peaks
, ,
'
H
with alkane alkyne H
- c- c-
with KMnOy shows we are working
or -
e c-
* Reacting ' '
n
/ "
" µ H
at 1375cm
Methyl group peak
µ
*
* R&D (7×2)+2-12
¥ 2 bonds
=
= =
z
@ normal pressure
↑
4. An organic compound has a percent composition, 89.84 %C, 10.17 %H. This compound has an approximate
boiling point of 152 °C at 757 mmHg. The IR spectrum of the neat thin film is shown below. Propose a
structure of this compound and show your rational for full credit.
Mono - substitute
C=c
sÑcarbÉ
Tert-butyl
sp3
0 7>0
Oop
= C
700
bending
-
H 690-900
* R&D -_
(10×24)--14--2=4
y§g
"
* Spr @ 73000cm
( 3000cm
* sp3 @ "
* Tert-butyl
double @ 1380cm
,
.a•←
* • panga,
Clo
* -170°C normal pressure bp
substitute
✓④
" -
mono
* 1650 -
1950cm
10 Carbons = 120g
* 13.58--14 H
12×01=89%1-1;
=
✗
•
5. Propose the major IR absorbance for an analog to an important anesthetic product.
Ester Tertiary Amine
← ethyl group
Aromatic Ring
O sp3 Athene
\ O / N
-
propyl group
/
/
! SPZ
/ I /
[Link] Sps 2
Primary Amine sp3 Sp
, ,
H2 N ,
Peaty '
3500-3300 cñ
Amine : N H stretch @
Primary
-
-
- 2 bands
"
-
N H bend @ 1640 -1560cm
-
"
N H absorption @ 800am
Oop
- -
(m)
_ '
@ 1350 -1000cm
-
C N stretch found
-
"
Amine : C N stretch Cmt @ 1350 -1000cm
Tertiary
- -
"
C- H stretch above 3000cm
Aromatic Ring : =
1600 and 1475cm
"
-
c=c ring
stretch in a
pair
bending @ 900 -690cm
"
€ -
Hoop
@ 840 -800 Cvs)
p Disubstituted
-
'
Region
-
2000 -1667cm
Overtone/ combination bands
Ester : stretch @ 1735cm
'
'
-
C=0
Ring strain
moves peak to higher strain '
stretch 2+ bands 1150 tooocm -
-
C -
O
"
3000cm
Alkene : = C -
H stretch above
"
= c- Hoop bend 1000 -650cm
"
around
A- thane? C-H stretch
3000 on
' '
Propyl : Doublet at 1370 and 1380cm
"
Methyl ? CH } @ 1375cm