Chemistry 30AL

Winter 2015

Final Exam on Thursday March 19

3:00 pm 6:00 pm in CS 76
You are allowed to bring ONE sheet (8.5" X 11") to the exam.
You may write anything on BOTH sides of the sheet.
Answers to Practice Problems
(1) (a) Majors steps in recrystallization:
Dissolve the impure product in a MINIMUM amount of a suitable hot solvent.
Filtering the hot solution to remove any insoluble impurities.
Let the solution to cool.
Filter the purified product.
The most important step in recrystallization is to pick a GOOD solvent.
(b) In recrystallizing the aspirin product we used ethanol / water Mixture
(2)

At end point equivalents of base = equivalents of acid

Equivalents of base = N x L
= 0.1500 N x 0.01L = 0.0015 equivalents
Equivalents = Wt / Eq. Wt.
Equivalent Wt. = 0.2725g / 0.0015 equivalents = 181.7 g/ equivalents

(3) Refer to the lecture guide and the Mohrig textbook for the theory on crystallization
(4)

75%

(5) Recrystallization purifies the product. Presence of small amount of impurities will usually
produce a marked depression of the melting point (melting point depression)
Crude product contained impurities, which will cause a large increase in melting point range
(6) (a) (I) When there is only one group substituted on the 6-membered aromatic ring you

have symmetry on the aromatic ring and only 4 lines will be seen. The three CH3s of the
trimethyl group are also identical. You wil get 7 lines.
The ketone will occur around 200ppm, there will be 4 lines in the 130 - 180 ppm region
due to the phenyl ring, and two lines in the aliphatic region around 35 and 25.
In the DEPT 90 spectrum you will see three of the lines in the 130 - 180 due to the three
types of CH group. In the DEPT 135 spectrum, you will see the line atttributed to the
CH3s (25ppm) as well as the three lines due to the CHs that were present in the DEPT
90.
(b) (I) These molecules will break on each side of the carbonyl, leaving the alkyl

C(CH3)3 (57) fragment or the phenyl fragment C6H5 and the other group with the CO
on it. You will also see a 15 due to methyl.
(II) These molecules will break off the OH and leave the t-butyl ion (MW 57).
(III) These molecules will lose a hydrogen and fragment giving the phenyl group.
(IV) Very similar to (III) but you will also see a 44 due to CO2

Answers to Practice Problems (Contd.)

(7)

(a) methyl acetate: 3 signals; 2-pentanone: 5 signals

(b)

Methyl acetate :

methyl carbon range 8-30 ppm

C-O carbon range 40-80 ppm
C=O carbon range 170-210 ppm

2-pentanone:

two methyl carbons range 8-30 ppm

two CH2 carbons range 15-55 ppm
C=O carbon range 170-210 ppm

(c) DEPT 90 spectrum will NOT be useful for these 2 molecules since it only detects CH
carbon.

(8) (a) 3 signals, (b) 5 signals, (c) 3 signals , (d) 2 signals , (e) 1 signal
(9)
(10)

The correct structure is (CH3) 2CHCH2CH(CH3) 2, which has # different carbons.

The correct structure is:
H2N

(11) First eluted ______ II _______

Reason: The ketone is the least polar of the oxygen functional groups; in addition
there are two nonpolar hydrocarbon groupan alkyl and an aryl group.
Second eluted ____IV_______
Reason: The aldehyde is slightly more polar than the ketone and this compound
has only one hydrocarbon groupa polarizable aryl group.
Third eluted _____III________
Reason: The alcohol is more polar than the aldehyde or ketone; there is only one
alkyl group.
Fourth eluted ________V___________
Reason: The two oxygens of the acid group make this the most polar compound of
the set. In addition the one hydrocarbon group is a polarizable aryl group.
(12) (a) 0.499; (b) 31.7%
(13) Rf = 5.7/13 = 0.44

(14)

(a) ethanol and water are miscible, you must use ether
(b) K = 1.78
(c) 14.4 gm

Answers to Practice Problems (Contd.)

(15) (a) Extract the mixture with water and ether. The caffeine and oxalic acid
will go into the aqueous layer, the salicylic acid will move into the ether layer.
Add salt to the aquous layer and extract with propanol as you did in class. The
caffeine will transfer into the porganic phase, the oxalic acid will stay in the
aqueous phase.
(b) Caffeine is a weak base, and can accept one proton/per molecule. Therefore,
equivalent weight = molecular weight.
Oxalic acid has two acidic groups; EW = 1/2 MW
Salicylic acid has one acidic proton; EW = MW
(16) The formula is C6H5Cl
(17) MnO4- + 8 H + + 5 e- = Mn 2+ + 4 H2O
C2O4-2

= 2 CO2 + 2 e-

(1) (Reduction)
(2) (Oxidation)

Multiply equation (1) by 2 and equation (2) by 5 yields:

2MnO4- + 16 H + + 10 e- = 2Mn2+ + 8 H2O
5C2O4-2

= 10 CO2 + 10e-

2MnO4- + 16 H + + 5C2O4-2

= 2Mn2+ + 10 CO2 + 8 H2O

(18) (a) the degrees of unsaturation = 4

To satisfy the degree of unsaturation compound could have:
(1) 4 double bonds; (2) benzene ring; (3) 4 rings; (4) 2 triple bonds, (5) 2 rings
and 2 double bonds, (6) 1 triple bonds and 2 double bonds, etc.
(b)

i. 3300 to 3600 cm-1

ii. 2800 to 3200 cm-1
iii. 1500 to 1600 cm-1
iv. 1000 t0 1300 cm-1

OH stretch
= C-H stretch in Alkene (aromatic
C-H stretch in alkane (alkyl group)
Aromatic ring (benzene ring)
C-O stretch