Organic Chemistry Laboratory Final Exam Chemistry 237

Exam Version A Fall 2009

Choose the most correct answer: (4 points each)

_____
E 1. If two compounds are close in boiling points, which might be a good technique to separate
them?
a. Simple Distillation because it offers a high number of theoretical plates
b. Simple Distillation because it offers a low number of theoretical plates
c. Gas Chromatography because it separates compounds based on molecular weight
d. Both Simple Distillation and Gas Chromatography are valid techniques
e. Gas Chromatography because it can separate compounds based on polarity

_____
D 2. For the following reaction:
PBr 3
CH 3 CH 2 CH 2 OH CH 3 CH 2 CH 2 Br

If 23.2g of 1-propanol is treated with an excess of phosphorous tribromide and

35.6 g of 1-bromopropane is isolated, what is the percent yield for the reaction?
[Atomic Weights: C-12; O-16; H-1; Br-80; P-31]
a. 24% c. 65% e. 93%
b. 50% d. 75%

_____
C 3. In the Who Has My Compound? experiment, how did the inorganic sand affect the melting
point of the benzoic acid?
a. increased the melting point
b. decreased the melting point
c. no effect on the melting point
d. broadened the melting point range
e. decreased the melting point range

_____
D 4. To purify a solid by recrystallization, it is desirable that the desired compound have a
different _____ from the impurities.
a. melting point
b. density
c. retention time
d. solubility
e. molecular weight

_____
B 5. In considering the conformations of n-butane generated by rotation about the C2-C3 bond,
how many different energy values will be encountered as energy minima?
a. One d. Four
b. Two e. An infinite number
c. Three

_____
C 6. The area of the peak recorded on a gas chromatogram is related to:
a. the boiling point of the compound
b. the shape of the compound
c. the relative amount of the compound
d. the molecular weight of the compound
e. the retention time of the compound

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

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B 7. Which of the following statements about thin layer chromatography is true?
a. Rf values can be used to positively identify a compound without the use of a standard.
b. It can be used to separate a mixture.
c. Two or more solvents cannot be used.
d. UV light is the only way spots can be detected.
e. Thin layer is the most easily quantitated chromatographic technique.

_____
E 8. In the dehydrohalogenation of 3-chloro-3,7-dimethyloctane there are three positional alkene
isomers produced because:
a. the alkyl halide is impure
b. hydrolysis, a competing reaction, is also taking place
c. the initially formed product rearranges
d. the ethanol used as a solvent contains a small percentage of water
e. the alkyl halide contains three different types of hydrogens that can be attacked by the
base

_____
C 9. Which of the following statements is true about eugenol?
I. It is an acetogenin.
II. It is a terpene.
III. It will give a positive Baeyer test.
IV. It will give a positive ferric chloride test.
a. all of these are true d. I and IV
b. I, II, and III e. II and III
c. I, III, and IV

_____
C 10. IR Spectroscopy is useful in the analysis of carbonyl compounds because:
a. the carbonyl group is chiral
b. carbonyl compounds are brightly colored
c. the C=O bond is a good absorber of particular frequencies of infrared radiation
d. carbonyl groups emit characteristic frequencies of infrared radiation
e. carbonyl rotational states are closely packed

E 11. A kinetic study of the SN1 solvolysis of 1-chloro-1-phenylethane showed a rate constant of
_____
4.0 x 10-1sec-1 in a solvent system that was 50:50 H2O/EtOH. With a solution of the same
concentration except in a solvent system of 70:30 H2O/EtOH, one would expect the rate
constant to be:
a. larger because of an increasing amount of less polar H2O
b. smaller because of the polar interactions between the alkyl halide and the increased
amount of H2O
c. smaller because an increase in H2O means that the cation will be better solvated and less
able to react
d. the same because the rate in an SN1 reaction depends only on the concentration of alkyl
halide
e. larger because an increased amount of polar H2O stabilizes the formation of the cation

_____
A 12. The reaction of an alcohol with hydrogen halide to give an alkyl halide works best with
a. tertiary alcohols d. secondary alcohols
b. primary alcohols e. phenols
c. cyclic alcohols

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

_____
B 13. Use the vapor-liquid Figure 1. Vapor-Liquid Composition for an Ideal Mixture of Two Liquids
composition diagram _ _
below to estimate the _ Vapor _
vapor composition upon 100
_ _
boiling of a liquid mixture _ _
which is 40%B. The _ _
vapor will contain about: _ _
a. 25% B _ _
b. 12% B Temperature _ _
OC 90
c. 80% B _ _
d. 88% B Liquid
_ _
e. 86E _ _
_
_ _
80
_ _
I I I I I I I I I
100% A 40% A 0% A
0% B 60% B 100% B
_____
A 14. The best method for the
separation of 100 g of a 50:50 mixture of mesitylene (1,3,5-tri-methylbenzene) (mp -45EC;
bp 162EC) and tri-N-propylamine (mp -93.5EC: bp 161.5EC) is:
a. extraction with 6M HCl
b. fractional distillation
c. preparative gas chromatography
d. recrystallization
e. thin layer chromatography

_____
B 15. At its melting point, an organic compound is:
a. in the solid phase only
b. in both the liquid and solid phases
c. in the liquid and gas phase
d. in the liquid phase only
e. an oily liquid

_____
E 16. In crystallization, if an oil forms what step(s) should be taken:
a. continue to cool the solution
b. bring the solution to a boil and cool
c. boil away part of the solvent
d. heat solution and filter
e. heat the solution to dissolve the oil and add a little more solvent

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

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A 17. Suggest the most efficient extraction sequence to isolate compound III from the following
mixture in dichloromethane

NH2 NH2
HO
EtO2 C
OCH 3
I II III IV

a. 3 N aqueous NaOH, 6 N aqueous HCl

b. 6 N aqueous HCl, 3 N aqueous NaOH
c. 3 N aqueous NaOH
d. 6 N aqueous HCl, 3 N aqueous NaOH, 6 N aqueous HCl
e. 6 N aqueous HCl

_____
D 18. Which structure below will have the highest strain energy when calculated by molecular
mechanics?
CH3 CH3
a. CH3 d.

CH3
CH3 CH3
e.
b. CH3
CH3
CH3

c.

CH3

_____
C 19. In preparative gas chromatography, increasing the quantity of injected sample will produce:
a. better separation
b. longer retention times
c. poorer separation
d. sharper peak shapes
e. no effect on separation or retention

_____
E 20. Which of the following statements are false for limonene and eugenol?
a. limonene is a terpene and eugenol is an acetogenin
b. limonene is obtained by isolation from citrus peel
c. eugenol is one of the compounds contained in clove oil which may be obtained by steam
distillation of cloves
d. eugenol reacts with FeCl3 reagent to give a dark green solution
e. both are phenols, so we could separate them by base extraction

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

_____
B 21. The organic product(s) of the following reaction is(are):

O
+ Br CH2CH CH2

O Br
a.
+ CH3CH CH2

O CH2CH CH2
b.

OH
c.
+ CH3CH CH2

CH2CH CH2
d.

e. no reaction occurs

D 22. The peak located at 1741 cm-1 wavenumbers corresponds to the vibrational frequency of what
_____
functional group?
1
Relative Transmittance
.4 .6 .2 .8

1741 cm-1

IR Spectra
Wavenumber (cm-1)
a. alcohol c. alkyne e. aromatic
b. alkene d. carbonyl

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

D 23. The rate law: rate = k[RCl][-OH] is representative of what type of kinetics?
_____
a. third order c. fourth order e. zero order
b. first order d. second order

_____
B 24. In the oxidation reaction of cyclohexanol to cyclohexanone, how many hydrogens are
effectively removed?

OH O
oxidation

a. 1 c. 3 e. 5
b. 2 d. 4

_____
A 25. A silver nitrate test is positive if
a. a white precipitate appears
b. the purple color vanishes
c. a color change from yellow to green is observed
d. a black precipitate appears
e. a color change from brown to clear is observed

_____
C 26. Which of the following is not an important requirement for the satisfactory separation of two
liquids by fractional distillation?
a. sufficient column length
b. extensive contact between the liquid and vapor phases
c. sufficient difference in densities of components
d. maintenance of the proper temperature gradient in the column
e. sufficient difference in boiling points of components

_____
A 27. After we have completed an organic reaction, we often “workup” the reaction. The term
“workup” refers to:
a. the general method of purification that uses aqueous-organic extraction
b. collection of crystals
c. the process of distillation
d. concentration or removal of the solvent from a reaction
e. the addition of a drying agent to a solution of the product

_____
D 28. What is the hybridization of the carbon atom and associated bond angles around carbon in
formaldehyde, CH2O?
a. sp and 120E d. sp2 and 120E
b. sp and 180E e. sp3 and 109.5E
2
c. sp and 109.5E

_____
A 29. If you have narrowed your search for your compound down to adipic acid and acetanilide,
what is a quick way to distinguish the two?
a. Determine its solubility in sodium bicarbonate
b. Perform a mixed melting point with both
c. Spot all three on a TLC plate and elute it
d. Perform the bromine test
e. Perform a mixed GC analysis with both

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

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B 30. If you started with 10g of 75% pure crystals, and recovered 5g of 100% pure crystals after a
recrystallization, how much of the product did you lose?
a. 2 grams c. 20% e. none
b. 2.5 grams d. 50%

_____
B 31. The strain energy of a molecule can be broken down into four term. What is the last one?
Estrain = Estretch + Eangle + Etorsion + ____ .
a. Esize c. Evibration e. Emechanics
b. Esteric d. Estrength

_____
C 32. The following compounds are dissolved in dichloromethane;

1. 4. CH CHCO2H

2. CO2H 5. Cl NH2

3. H3C NH2

The solution is extracted with 3M sodium hydroxide. The compounds present as salts in the
aqueous layer are:
a. 1 only c. 2 and 4 e. 1 and 3
b. 3 and 5 d. 3 and 4

_____
E 33. Having just completed the Thin Layer Chromatography experiment, you find that caffeine
gives an Rf of 0.75 in the 75% ethyl acetate – 25% hexane solution. Out of curiosity, you
decide to run a second TLC plate in hexanes. What should you expect to see and why?
a. A lower Rf because the hexanes are a more polar solvent system
b. A higher Rf because the hexanes travel up the TLC plate faster
c. A higher Rf because the hexanes are a less polar solvent system
d. A lower Rf because the hexanes travel up the TLC plate faster
e. A lower Rf because the hexanes are a less polar solvent system

_____
D 34. Steam distillation is a good method for the isolation of high boiling compounds because the
vapor pressure for an immiscible mixture is equal to the ____________ of the two
compounds’ vapor pressures.
a. quotient
b. product
c. difference
d. sum
e. square

_____
C 35. The role of benzyltri-n-butylammonium chloride in the phase transfer catalyst experiment is
a. to carry allyl naphthyl ether into the organic phase
b. to carry NaOH into the organic phase
c. to carry the naphtholate anion into the organic phase
d. to carry the allyl bromide into the organic phase
e. to raise the temperature of the reaction

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

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C 36. What is expected as the major product from the following reaction?

CH3
heat
H3C C Cl + NaOH ethanol ?
CH3

CH3
a. H3C C O Na + NaCl
CH3

CH3
b. H3C C OH + NaCl
CH3

CH3
c. CH2 C + H2O + NaCl
CH3

CH3 CH3
d. H3C C O C CH3 + NaCl
CH3 CH3

CH3
e. H3C C OCH2CH3 + NaCl
CH3

_____
A 37. By plotting the natural logarithm (ln) of the initial concentration of alkyl halide ([RCl]0) over
the concentration of alkyl halide at any time ([RCl]t) as function of time for a first order
reaction, the plot will yield:
a. A Straight line with slope equals the rate constant k
b. A straight line with slope equals the initial concentration of alkyl halide ([RCl]0)
c. A hyperbola with slope equals the rate constant k
d. A hyperbola with slope equals initial concentration of alkyl halide ([RCl]0)
e. A straight line with slope equals zero

_____
E 38. Why is sodium hypochlorite preferred over chromic acid as an oxidizing agent?
a. chromic acid is too strong an oxidizing agent
b. chromic acid is too expensive
c. chromic acid is too weak an oxidizing agent
d. sodium hypochlorite is a better reducing agent
e. chromic acid forms toxic salts

_____
A 39. The preparation of 3-chloro-3,7-dimethyloctane is achieved via a(n) _____ reaction.
a. SN1 c. E1 e. a and c
b. SN2 d. E2

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

_____
B 40. Which of the following statements concerning the preparative gas chromatography
experiment is WRONG?
a. IR was used to analyze unknowns.
b. A flame ionization detector was the detector used.
c. Samples must be thermally stable and volatile for running GC.
d. Peak area is sometimes proportional to sample amount.
e. Compounds with the same boiling points may be separated by prep GC.

A 41. Which of the following molecules are expected to be sp3 hybridized?

_____

A B C D
a. A, B, C
b. A, C
c. B, C
d. B, C, D
e. A, B, C, D

_____
A 42. Which technique would be best for the purification of a mixture which contained a large
amount of a solid material with a small amount of liquid contamination. Both the liquid and
solid are soluble in organic solvent.
a. recrystallization
b. simple distillation
c. extraction
d. preparative gas chromatography
e. fractional distillation

_____
D 43. In the Who Has My Compound? experiment, the solubility of your sample was tested in what
solution?
a. dilute hydrochloric acid
b. dilute sodium hydroxide
c. saturated sodium chloride
d. dilute sodium bicarbonate
e. saturated sodium carbonate

_____
D 44. The global minimum energy for conformations of butane occurs when
a. The dihedral angle is less than 60°
b. C1 and C4 are eclipsed
c. The C2-C3-C4 bond is less than the ideal 109.5°
d. C1 and C4 are in an anti conformation
e. This molecule cannot adopt a global minimum geometry

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Organic Chemistry Laboratory Final Exam Chemistry 237
Exam Version A Fall 2009

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E 45. During an extraction procedure you add equal amounts of the following:
• water (Density = 1g/mL)
• dichloromethane (Density = 1.3266 g/mL)
• ethyl acetate (Density = 0.897 g/mL)
• 5% NaOH solution (Density = 1.055 g/mL)
How many layers do you expected to see in the funnel and which one will be the bottom layer?
a. 3 layers, aqueous phase d. 4 layers, organic phase
b. 3 layers, organic phase e. 2 layers, organic phase
c. 2 layers, aqueous phase

_____
D 46. To obtain best results when performing thin layer chromatography, one must:
a. wash the TLC jar with water to make sure it is clean before beginning the experiment.
b. make sure that the solvent line develops to the top of the TLC plate so maximum
separation can be achieved.
c. make sure the developing solvent covers the sample spots at the origin when the TLC
plate is placed in the jar.
d. Make sure that the top of the TLC jar is capped so it is air tight.
e. While the TLC plate is developing, be sure to move the plate around in the jar so that the
solvent line develops evenly.

_____
E 47. You used phase transfer catalysis to carry out which of the following types of reactions?
a. E1 elimination d. SN1 substitution
b. E2 elimination e. SN2 substitution
c. electrophilic substitution

_____
E 48. The dehydrohalogenation of 3-chloro-3,7-dimethyloctane with KOH in ethanol
a. gives a mixture of four alkanes
b. involves competing elimination and substitution reactions, with the substitution being
favored over elimination
c. is an example of an SN1 reaction
d. is an example of a electrophilic substitution reaction
e. is an example of a E2 reaction

B 49. 3-pentanol has an O-H peak from alcohol at? (All numbers are in cm-1)
_____
a. 1050-1300 d. 1670-1830
b. 3200-3600 e. 600-800
c. 2500-3300

_____
C 50. In the oxidation of cyclohexanol to cyclohexanone with bleach solution, the oxidation state of
what element is reduced?
a. Cr
b. hydrogen
c. Cl
d. O (of hypochlorous acid)
e. C (attached to C=O of acetic acid)

— — — — — THIS IS THE END OF THE EXAM — — — — —

Chemistry 237 Exam Version A Page 12 of 12