Chem 31.

1 Midterm Exam Reviewer

I.

True or False
1. In Lucas test, the ZnCl2 is a Lewis base which helps make the OH- a better leaving group.
2. 1,2,3-propanetriol has a solubility classification of S 2 since it dissolves in water but not in 5% NaOH.
3. Most of the time, paper chromatography is a reverse-phase chromatography.
4. Neutral compounds, class N, react with sulfuric acid by electrophilic substitution.
5. Halogens are electron-donating groups that are ortho,para-directors.
6. In paper chromatography, phenol is expected to have a higher Rf value than p-nitrotoluene.
7. An iodine chamber may be used to visualize a chromatogram with bands of conjugated compounds.
8. Hexane undergoes free radical addition upon addition of Br2 in the presence of light.
9. Toluene and cyclopentene give positive result in Baeyers test and in Br 2 under light conditions.
10. There are 9 stereocenters in this sucrose molecule.

II.
1.

Multiple Choice
Phenol is soluble in 5% aqueous NaOH solution because of:
a. H-bonding with the solvent
b. The formation of a resonance-stabilized anion
c. Strong van der Waals interaction
d. Phenol is insoluble in 5% aqueous NaOH solution

2.

Which of the following is a limitation and an advantage of sublimation as a purification technique, respectively?
a. It involves many steps, high percent recovery
b. Not all solids can be purified by sublimation, low percent purity
c. Low percent yield, almost 100% purity
d. Uses water as a solvent, simple one step process

3.

2-methyl-2-hexene and 2-methyl-2-hexanol can be differentiated using:

a. KMnO4
b. Br2 in light
c. AlCl3, t-BuCl
d. None of the above

4.

Arrange the following alcohols in INCREASING order, based on the formation of layers/emulsification with the Lucas
reagent:
i. 2-methylbutanol
ii. 3-methyl-2-butanol
iii. 2-methyl-2-butanol
a. iii < ii < i
c. ii < iii < i
b. i < ii < iii
d. iii < i < ii

5.

The molecules shown on the right are:

a. Enantiomers
b. Mesomers
c. Diastereomers
d. Identical
The following are important features of a steam distillation set-up, except:
a. Pressure regulator is submerged in water
b. Water-in is near the receiving flask
c. Thermometer is place in the sample round-bottom flask
d. More heat is applied to the sample round-bottom flask

6.

7.

In the synthesis of tert-butyl chloride, all of the following will decrease the yield except:
a. Anhydrous CaCl2 was added into the crude product before distillation
b. Saturated NaHCO3 solution was added to remove excess HCl
c. The mixture was allowed to separate for 5 minutes
d. Thirty (30.0) mL of 1.0M HCl was used

8.

A compound yielded an immediate positive result with Lucas test. Upon addition of KMnO4 to the compound,
decolorization was observed. What could be the compound?
a. Pentanol
c. tert-butanol
b. 2-pentanol
d. Benzyl alcohol

9.

Which of the following statements is/are TRUE?

I.
Primary alcohols are oxidized to aldehydes
II.
Secondary alcohols react with KMnO4 to form brown precipitate
III.
Secondary alcohols are oxidized to carboxylic acids
IV.
Benzaldehyde, like tertiary alcohols, do not react with KMnO 4

a.
b.

I & III
II & III

c. I only
d. III only

10. Arrange the following compounds in increasing rate of EAS.

a.
b.

I < II < III < IV

II < I < III < IV

c. I < II < IV < III

d. II < I < IV < III

III. Problem Solving

1. Sir Ser (Sir2) Laboratories, Inc., a multi-million dollar pharmaceutical company, is in search of prostaglandin analogues
for the treatment of glaucoma. In one of the companys laboratories, a team of organic chemists composed of John and
Lynon (aka JL) synthesized a prostaglandin analogue that controls the progression of glaucoma by reducing intraocular
pressure. The structure of the compound, which they call as Latanoprost is shown below.

Given the structure:

a. Determine the absolute configuration of stereocenters (a), (b), and (c).
b. Give the correct structure of Latanoprost by:
i.
Converting the structure above to its Z isomer
ii.
Drawing the R configuration of stereoisomers (d) and (e) using the wedge-dash representation.
c. How many stereoisomers can it possibly have?

2.

A mixture containing 7.0 g of crystal A, 6.0 g of crystal B, and 9.0 g of crystal C needs to be separated using
recrystallization (100mL of solvent was used). The solubilities of the crystals per 100 mL of solvent are shown below.

solvent
Methanol
Diethyl ether

A(very polar)
Hot
Cold
14.2 4.30
2.10 0.60

B(slightly polar)
Hot
Cold
7.30
0.70
15.1
3.20

C(nonpolar)
Hot Cold
4.20 0.60
11.2 0.40

a.
b.
c.

What solvent will you use to separate the crystals? Justify using a schematic diagram.
What are the % purity and % recovery of the three crystals? Show your calculations.
Which crystal has the highest purity? Will a second round of recrystallization using 50 mL of the same solvent improve
the purity? Prove using calculations.

3.

You have extracted a compound from a tadpole that was trapped in your Gatorade/Sola bottle when you took your
water sample from AS pond. Due to curiosity, you subjected the extract to a paper chromatography analysis and found
out that your extract is made up of four components, namely A, B, C, and D.
With the help of your ever-reliable instructor, you were able to separate and determine the structures of the four
components. The structures of given below:

Upon further experimentation, you found out that B gives a positive result with Br2 in dark condition; C gives a positive
result with Friedel-Crafts alkylation; and D gives a positive result with potassium permanganate.
a.
b.
c.
d.

e.

Determine the identities of A, B, C and D.

Identify the solubility classes of A, B, C and D.
Draw the paper chromatogram obtained after doing the experiment. Label each spot as A, B, C or D.
What was the visible observation when:
i. B was reacted with Br2 in dark condition
ii. C was reacted with Friedel-Crafts reagent
iii. D was reacted with KMnO4
All of the compounds will give positive result with one functional group test. What is this test?