CHM2211L Lab Exam – Summer 2022

Be sure to bubble in your name and UF ID number on your Scantron sheet. When you finish the quiz, turn in
the Scantron to the TA proctors. You may take this question packet with you.

***This exam consists of 35 questions. Choose the best answer and bubble in your response on the Scantron
sheet.***

1. Safety glasses are no longer required in the lab once a student finishes an experiment and locks their
drawer.

a) True b) False

2. Two students synthesized aspirin (lit. m.p. = 135°C) and measured melting points of their samples: Student
A recorded 131-135°C and Student B recorded 133-134°C. Which statement is correct about these samples?

a) Sample A is more pure than sample B.

b) Sample A is less pure than sample B.
c) Both samples are equally pure.
d) Purity cannot be determined using melting point.

3. How could 1H NMR distinguish between 1-Butanal and 2-Butanone?

a) 4 signals are expected for 1-Butanal and 3 signals are expected for 2-Butanone
b) 1-Butanal is expected to have one signal that has an integration value of 1, but 2-Butanone will not.
c) 1-Butanal is expected to have a sextet but 2-Butanone will not
d) All of the above
e) Aldehydes and ketones cannot be distinguished by 1H NMR

4. When do you record the first temperature within the melting point range of a sample?

a) When the sample starts to compress

b) When you see the first drop of liquid in the capillary
c) When the entire sample in the capillary is a liquid
d) When you press start on the instrument
5. A student was asked to prepare 8 mL of a 6:4 eluent solution of solvent A: solvent B for their TLC
developing chamber. What volumes of solvent A and solvent B are needed to prepare the requested eluent
mixture?

a) 4.4 mL of solvent A and 3.6 mL of solvent B

b) 4.4 mL of solvent A and 2.9 mL of solvent B
c) 4.8 mL of solvent A and 3.2 mL of solvent B
d) 5.4 mL of solvent A and 2.6 mL of solvent B

6. All compounds that act as dyes contain a chromophore.

a) True b) False

7. Letícia and her group are trying to determine the distribution coefficient as part of their extraction lab.
They dissolved 1.50 grams of benzoic acid in 75 mL of water and used 75 mL of diethyl ether to extract it.
After the extraction was completed, Letícia noted they’d been able to extract 1.35 grams. What is their
distribution coefficient? Recall that Kd = (concentration in organic phase)/(concentration in aqueous
phase).

a) 9 b) 0.1 c) 0.9 d) 1.1

8. Assume that you dissolved a mixture of benzoic acid and phenol in diethyl ether, and then extracted with
aqueous NaHCO3. Which equation represents the species present after this extraction?

a)

b)

c)

9. Changing the moles of which of the following will affect the number of repeat units in a chain addition
polymer?

a) Initiator b) Monomer c) catalyst d) both (a) and (b) e) all of these

10. The purpose of using a trap during vacuum filtration is to catch any overflowing filtrate before it can enter
the house vacuum system.

a) True b) False
11. When aqueous 2 M HCl is added to an organic phase inside a separatory funnel, a new layer forms at the
bottom of the funnel as the organic phase rises to the top. Which of the following can be concluded based
on this observation?

a) Most of the major product is present in the aqueous layer

b) Most of the major product is present in the organic layer
c) The solvent in the organic phase has a density greater than 1 g/mL
d) The concentration of the aqueous phase is less than the concentration of the organic phase
e) The solvent in the organic phase has a density less than 1 g/mL

12. What should you do if some of your product still remains in the reaction flask when you are trying to collect
it via vacuum filtration?

a) Dissolve the product, and pour the solution into the Büchner funnel
b) Use some of the reaction solvent to transfer the product into the Büchner funnel
c) Dissolve the product, and pour the solution into the liquid waste
d) Wait for the product to be mostly dry, and then scrape it into the solid waste
e) Dispose of the flask in the solid waste and obtain a replacement from the stockroom

13. Consider a sample comprised of two components A and B. When the sample was spotted on a TLC plate
and eluted using 50:50 of hexane/ethyl acetate, the results were as shown below. If you made a new TLC
plate of the same sample and eluted with 70:30 of hexane/ethyl acetate, what change in Rf values would
you expect to see?

a) The Rf values of both A and B will remain the same

b) The Rf value of both A and B will increase
c) The Rf value of both A and B will decrease
d) The Rf value of A will decrease, while the Rf value of B will increase
e) The Rf value of A will increase, while the Rf value of B will decrease

14. A student reacted 1.43 grams of salicylamide (137.14 g/mol) and 1.72 grams of sodium iodide (149.89
g/mol) to produce iodosalicylamide (263.03 g/mol). Calculate the theoretical yield for this transformation.

a) 2.51 g
b) 2.74 g
c) 3.02 g
d) 3.15 g
e) 3.30 g
15. A student was carrying out a reaction in the organic lab. At a point during the reaction, the reaction
mixture (R) was spotted on a TLC plate along with a reference of the starting material (S) which is the
limiting reagent. The plate was then eluted with 60:40 hexane/ethyl acetate. What can you conclude
about the reaction from the TLC results shown here?

a) The reaction is complete, and there are two products formed

b) The reaction is not yet completed since there is unreacted starting material present
c) The product of the reaction is more polar than the starting material
d) Both (b) and (c) are correct
e) None of these statements are correct

16. If 100 g of oleic acid triglyceride (885.4 g/mol) is converted to oleic acid methyl ester (296.5 g/mol) using
excess methanol and KOH according to the equation below. How many grams of glycerin (92.1 g/mol) by
product are formed?

a) 104 g
b) 35 g
c) 10.4 g
d) 31 g

17. Plate X represents the TLC of a compound that was separated using a 70:30 hexane/ethyl acetate mixture.
Which plate corresponds to the results that would be observed on a longer plate, using the same solvent
mixture?

a) Plate A b) Plate B c) Plate C d) no way to predict

18. Ethanol is formed during the cyclization reaction shown here:

a) True
b) False

19. What was the role of Dowex 50WX4 beads in the coumarin synthesis?

a) acid b) base c) drying agent d) nucleophile e) filter agent

20. The chemical transformation involving the conversion of vegetable oil into biodiesel can be called:

a) Saponification
b) Transesterification
c) Hydrolysis
d) Gasification
e) None of the above

21. What type of chemical interaction(s) will cause a dye to adhere to a piece of fabric?

a) vander Waals attractions

b) hydrogen bonding
c) covalent bonding
d) all of the above

22. Which of the following is not a valid resonance structure for 4-(diethylamino)salicylaldehyde (shown at the
right):

a) b)

c) d)
23. ______ is often formed as an undesired by-product during the reaction that produces biodiesel.

a) Glyceraldehyde b) Soap c) Ethylene glycol d) None of these

24. What type of organic reaction is the aryl diazonium coupling shown below?

a) Electrophilic aromatic substitution

b) Nucleophilic aromatic substitution
c) E2 elimination
d) SN1 substitution
e) SN2 substitution

25. A student’s notebook entry is given below for the synthesis of Nylon 10,6 that was done during the
polymers lab. Consider the underlined statements, and indicate how many of these statements are
incorrect.

“The Nylon-10,6 is a polyester polymer which was synthesized from sebacoyl chloride and
hexamethylene diamine as shown above. This is an example of a condensation polymerization
where water was obtained as the byproduct. The product (Nylon-10,6) was readily soluble in
organic solvents such as toluene and acetone.”

a) 1 b) 2 c) 3 d) 4 e) no incorrect statements

26. A student was setting up a block copolymer reaction, and while he was transferring the reactants to the
vial, he dropped a small amount of the initiator on the benchtop. How will this impact the molecular
weight of the polymer that is formed?

a) lower MW than expected b) higher MW than expected c) no impact on molecular weight

27. Consider the formation of the coumarin derivative shown below. If you wanted to make 4.75 grams of
product, how many grams of 4-(diethylamino)salicylaldehyde should be used?

a) 2.38 g b) 3.54 g c) 6.37 g d) 7.05 g e) none of these

28. When performing a polymerization, why is it important to know the exact amount of initiator used?

a) The initiator is highly reactive and can dimerize if used in excess.

b) When too much initiator is used, the molecular weight of the polymer will be higher than expected.
c) The amount of initiator determines the number repeat units in the polymer.
d) The initiator requires a catalyst to react.

29. A 1H NMR spectrum of an organic molecule showed two signals: a triplet and a quartet. Which of the
molecules shown would exhibit this splitting pattern?

a) b) c) d) e) more than
one of these

30. A student carried out an organic synthesis and obtained 2.63 grams of crude product. The student decided
to recrystallize 1.50 grams of the product, and they recovered 1.28 grams of pure material. What is the
percent recovery for the recrystallization?

a) 49% b) 57% c) 74% d) 85% e) 90%

The next five (5) questions relate to the reaction shown below:

31. Reaction progress can be monitored by TLC. Which TLC plate would indicate the reaction is complete?

32. If the reaction was conducted using 3.25 grams of 4-chlorobenzaldehyde, what is the theoretical yield of 4-
chlorobenzoic acid (in grams)?

a) 1.46 grams b) 1.81 grams c) 2.92 grams d) 3.62 grams

33. After the reaction is complete, the product mixture is dissolved in ether and extracted with two portions of
sodium bicarbonate solution. Which compound remains in the ether layer after this extraction?

a) (4-chlorophenyl)methanol b) 4-chlorobenzoic acid

34. How would you collect the product contained in the aqueous layer after the extraction?

a) Dry with anhydrous magnesium sulfate, decant, and evaporate under reduced pressure.
b) Neutralize with dilute acid, then evaporate under reduced pressure.
c) Neutralize with sodium hydroxide, then collect product using vacuum filtration.
d) Neutralize with dilute acid, then collect product using vacuum filtration.

35. After completing the reaction and isolating both products, you went out for a lunch break but you were so
hungry that you forgot to label the products before you left the lab. How can you tell them apart using IR
spectroscopy?

a) The alcohol product will show a signal at about 3500 cm-1 but the carboxylic acid will not.
b) The carboxylic acid will have a signal at about 1730 cm-1 but the alcohol will not.
c) It isn’t possible to distinguish these molecules using IR alone.