CHM 258
Week of 4/8/13
Organic Lab
(30 pt.)
Atomic weights: C = 12.011 g/mole
Quiz 2 Name ______________________
H = 1.0079g/mole
O = 15.9994 g/mole
(There is a table of IR frequencies at the end of the quiz that may be helpful.)
1. (2 pt.) The following structure represents a catalytic site in a zeolite.
catalytic site?
Si
O
Al
O
Si
O
Si
Circle what type of catalyst it is.
Bronsted acid
Lewis Acid
Bronsted Base
Lewis Base
Transition metal
2. (2 pt.) a. What are the three main elements found in a zeolite framework? Do not include the metal
counterion for this part. b. What was the counterion for the zeolite used in Exp. 6.
a.
b.
3. (2 pt.) If in a deconvolution experiment, mixtures M2 and M4 show drug activity, what will be the
binary A-B compound responsible for the drug activity?
M1
A1
M4
M5
M6
B1
B2
B3
M2
A2
M3
A3
4. (2 pt.) What is the main reason one would choose to perform a vacuum distillation instead a distillation
at ambient (or atmospheric) pressure?
5. (6 pt.) For the reaction provided, if 15.9 g. of A reacted with 70.5 g. of ethanol, what is the theoretical
yield of the reaction? If 13.6 g. of B formed, what is the % yield?
O
O
O
C
C
HO
A
C
+ 2 CH3CH2OH
OH
O
C
H3CH 2CO
OCH 2CH 3
B
6. (4 pt.) List 4 ways in which exposure to chemical hazards can be eliminated when performing a
specific chemical reaction.
7. (6 pt.) Calculate the atom economy for the product ester for the following reaction. Do not use the acid
catalyst in your calculation.
8. (6 pt.) Which one of the following five compounds is responsible for the IR and mass spectra?
Explain.
O
O
H3C
H2C
H3C
H2C
CH3
CH3
cinnamaldehyde
cumminaldehyde
CH3
OCH3
OH
H
H
O
OCH3
Eugenol
Estragole
carvone
Infrared Spectroscopy Table
Lowe
r
Uppe
r
540
685
690
760
685
770
CCl stretch
cis-RCH=CHR (oop) (s)
monosubstituted benzene (oop) ( m to s)
720
720
Rocking, for chains > 4 carbons
734
735
743
770
Propyl chain
ortho substituted benzene (oop) (m to s)
770
800
880
790
860
780
890
900
900
935
965
1000
1015
1025
1090
1180
1190
1200
1250
1300
950
990
900
935
965
1280
1065
1060
1140
1360
1190
1200
1250
1300
Ethyl chain
para substituted benzene (oop) (m to s)
meta substituted benzene (oop) (m to s)
epoxide asymmetric stretching of ring (biggest peak if
present)
RHC=CH2 out of plane bending (oop) (s)
R2C=CH2 (oop) (strong)
O-H (oop)
trans-RCH=CHR (oop) (s)
Ester C-O (very big peak)
cyclic alcohols
primary alcohols
secondary and tertiary alcohols
aromatic amines
OCH3
methyl ester triplet
epoxide symmetric ring stretch (vs)
coupled C-O stretch in COOH
1370
1385
Gem-dimethyl doublet (and tert-butyl) (w)
1375
1420
1375
1420
Symmetric bend (methyl group)
coupled C-O stretch in COOH
1450
1510
1580
1590
1625
1640
1645
1650
1650
1655
1660
1670
1475
1650
1900
1650
1625
1670
1645
2000
1715
1655
1660
1670
Asymmetric bend and scissor
N-H secondary amine deformation
Carbonyl
N-H primary amine deformation
ß-diketones
amide II band
RCH=CH2 (w)
benzene substitution pattern region
amide carbonyl (amide I band)
R2C=CH2 (w)
cis-RCH=CHR (w)
R2C=CHR and R2C=CR2 (w)
Description
Group
Chlorides
Alkenes
Aromatic
Methyl, Methylene,
Methine
Methyl, Methylene,
Methine
Aromatic
Methyl, Methylene,
Methine
Aromatic
Aromatic
Rings
Alkenes
Alkenes
Carboxylic
Alkenes
Esters
Alcohols
Alcohols
Alcohols
Amines
Ethers
Esters
Rings
Carboxylic
Methyl, Methylene,
Methine
Methyl, Methylene,
Methine
Carboxylic
Methyl, Methylene,
Methine
Amines
Carbonyls
Amines
Carbonyls
Amides
Alkenes
Aromatic
Amides
Alkenes
Alkenes
Alkenes
1675
1700
1710
1720
1740
1750
2000
2100
2200
2210
2500
2700
2760
2815
1675
1720
1760
1740
1750
1820
3000
2140
2300
2260
3200
2900
2820
2830
trans-RCH=CHR (w)
ketones (very strong)
C=O
aldehydes (vs)
Ester C=O
C=O (s two bands)
ammonium band
CC external (small)
CN stretch (s, sharp)
CC internal (small)
O-H dimer peak (broad)
aldehyde CH (w, 2 peaks)
N-methyl amines
methyl ether band
2850
2990
3000
3020
3024
3080
3103
3200
3270
2990
3056
3100
3020
3024
3080
3103
3400
3315
3300
3450
3603
3611
3620
3633
3500
3500
3611
3619
3625
3639
-CH3 and-CH2- and CH (s) (sp3 C-H bonds)
epoxides
C-H asymmetric stretch
=CHR asymmetric stretch (m to s) (sp2C-H bonds)
cyclopropane symmetric stretch
=CH2 asymmetric stretch (m to s) (sp2 C-H bonds)
cyclopropane asymmetric stretch
alcohols polymers (s, broad)
CH (s, sharp) (small)
primary amines (doublet), secondary amines (singlet) (s,
broad)
alcohol dimers (s, broad)
aromatic alcohols (dilute)
tertiary alcohols (dilute)
secondary alcohols (dilute)
primary alcohols (dilute)
Alkenes
Carbonyls
Carboxylic
Carbonyls
Esters
Anhydride
Amines
Alkynes
Nitrile
Alkynes
Carboxylic
Carbonyls
Amines
Ethers
Methyl, Methylene,
Methine
Rings
Aromatic
Alkenes
Rings
Alkenes
Rings
Alcohols
Alkynes
Amines
Alcohols
Alcohols
Alcohols
Alcohols
Alcohols