Organic Chemistry Laboratory Final Exam A 1.

Chemistry 242 December 4, 2001

You have separate test tubes containing each of the following substances. You analyze each substance using broad-range pH paper. You compare the color of the paper after the analysis to the reference. Which of the following would you anticipate showing a pH of greater than 7? aqueous ammonia-based 0.01N HCl lemon juice 0.05 N NaOH baking soda cleaner a. b. c. d. e. A B C A, C, and E would have a pH > 7 B and C would have a pH > 7 only C and E would have a pH > 7 all of the substances would have a pH > 7 none of the substances would have a pH > 7 D E

2.

In the Preparation of Aspirin, iron (III) chloride test positive (purple) for a. a carbonyl c. a phenol e. b. an acetyl group d. an ester By definition a melting point is: a. The temperature when solid-liquid equilibrium is reached. b. The temperature when liquid-vapor equilibrium is reached. c. The temperature when a solid decomposes. d. The temperature at which sublimation occurs. e. none of these Casein is a _________ that is found in _________ . a. protein / vegetable oil b. enzyme / fruits c. carbohydrate / milk

an amide

3.

4.

d. e.

lipid / animal fat protein / milk

5.

If a substance gives an Rf value of 0.50 and the solvent front traveled 12.6 cm from the origin, then how far did the sample spot travel from the origin? a. 6.3 cm c. 6.0 cm e. none of these b. 25.2 cm d. 1.0 cm Examine the following compound and determine which of the circled H's (i.e., protons) you would expect to be the most acidic.
O i H H ii O O O H iii H iv

6.

a. b. c.

i would be the most acidic ii would be the most acidic iii would be the most acidic

d. e.

iv would be the most acidic iii and iv are identical in acidity and are the most acidic

Exam A, Page 2 of 8

Organic Chemistry Laboratory Final Exam A 7. Soaps are __________. a. salts of strong bases and weak acids b. salts of strong acids and weak bases c. a glycerol with fatty acid side chains d. triglycerides such as tristearin e. strictly hydrophobic How many double bonds are involved in the conjugated system shown below.

Chemistry 242 December 4, 2001

8.

a. b. 9.

1 2

c. d.

3 4

e.

Starch can form an intense dark blue/violet color with which of the following reagents? a. Fehlings Reagent d. iodine b. Tollens Reagent e. none of these c. milk

10. Urushiol, a mixture of phenolic compounds (e.g. tetrahydrourushiol), is: a. a tropical antipyretic d. the irritant (allergen) in poison ivy b. a sweetening agent e. antifreeze c. a flavoring agent 11. Which of the following is false about the preparation of aspirin? a. Phosphoric acid acts as a catalyst to speed up the reaction. b. Unreacted salicylic acid gave a purple color when tested with 1% iron (III) chloride solution. c. The unreacted acetic anhydride was destroyed by treating with ice/water mixture. d. Acetylsalicylic acid is highly soluble in water. e. Salicylic acid is the structure that gives aspirin it therapeutic properties. 12. Examine the following TLC plate and determine the Rf value for compound R.
5 cm 4 cm

X origin solvent front cmpd R

a. b. c.

Rf = 4 5 = 0.8 Rf = 4 x 5 = 20 Rf = 4 (5 + 4) = 0.44

d. e.

Rf = 5 (5 + 4) = 0.56 Rf = 5 4 = 1

Exam A, Page 3 of 8

Organic Chemistry Laboratory Final Exam A

Chemistry 242 December 4, 2001

13. Solid animal fats contain mostly _______ fatty acids. Vegetable oils contain high amounts of ______ fatty acids. a. unsaturated; unsaturated d. saturated; solid b. saturated; saturated e. saturated; unsaturated c. unsaturated; saturated 14. The preparative method used in lab to separate tomato juice pigments was called a. paper chromatography d. gas chromatography b. column chromatography e. infrared spectroscopy c. thin layer chromatography 15. Which of these compounds has a sweet and pleasant smell? a. acetic acid c. ethyl butrate b. formic acid d. octanoic acid 16. Soap is impractical to use in hard water because it forms a ______. a. toxic gas c. radioactive species b. precipitate d. emulsifying agent 17. Which fruit/vegetable contains a significant quantity of lycopene? a. carrots c. cabbage b. rutabagas d. grapes 18. Which of the following is a carbohydrate? a. casein c. triglycerides b. starch d. methyl salicylate

e.

butanoic acid

e.

none of these

e.

tomatoes

e.

lycopene

19. The ferric chloride test would yield a positive result for which of the following reagents? a. salicylic acid d. both a and c b. acetylsalicylic acid (aspirin) e. both a and b c. phenol 20. What is the theoretical yield of aspirin if one begins with 3 grams of salicylic acid. You may assume that salicylic acid is the limiting reagent.
CO 2 H OH + CH 3 salicylic acid MW = 138 g/mol O C O O C H+ CH3 CO 2 H O C O aspirin MW = 180 g/mol CH 3 + HO O C CH 3

a. b.

2.8 grams 4.2 grams

c. d.

2.3 grams 3.0 grams

e.

3.9 grams

Exam A, Page 4 of 8

Organic Chemistry Laboratory Final Exam A

Chemistry 242 December 4, 2001

21. Predict the bond angles for the following hydrocarbon:

H C CH3 i CH2 C ii CH3 CH3

a. b. c.

i = 120 and ii = 120 i = 120 and ii = 109.5 i = 109.5 and ii = 180

d. e.

i = 109.5 and ii = 109.5 i = 180 and ii = 120

22. Which chemical process is called saponification (soap making)? a. acid-catalyzed esterification b. acid-catalyzed ester hydrolysis c. base-promoted ester hydrolysis d. the iodoform test e. the Lucas test 23. What is the functional group in the figure shown? a. b. alkane alkene c. d. alkyne aromatic
CH 3C CCH 3

e.

amine

24. What are the expected products of a neutralization reaction? a. a salt c. nitric acid b. water d. a salt and water

e.

none of these

25. Which compounds are normally used to saponify triglycerides? a. NaOH, and CH3OH d. H2O and CH3CH2OH b. NaCl and KCl e. FeCl3 and CaCl2 c. aqueous NaOH or KOH 26. When tested with aqueous KMnO 4, which compound(s) below would not provide a brown precipitate of MnO 2?
CH3 CH3CH2CH(CH3)2 A B CH3 C C C CH3 CH3 (CH3)2CHCO2H D E

a. b. c.

D and E A and C B, D and E

d. e.

B and E all of these compounds would yield a precipitate of MnO 2

Exam A, Page 5 of 8

Organic Chemistry Laboratory Final Exam A

Chemistry 242 December 4, 2001

27. Yikes! I was so stressed over my finals, I accidentally swallowed some mercury nitrate. My roommate, being a brilliant organic chemist, gave me some milk and eggs and rushed me to the hospital. Why did she give me the milk and eggs? a. the base in the food will neutralize the mercury b. the protein in the food will complex the mercury before my body absorbs it c. to remove the mercury through esterification d. the food acts as a catalyst and speeds my bodys natural defenses e. she is not as brilliant as I thought 28. Which of the following terms best characterizes 2-methyl-3-pentanol? a. primary alcohol c. tertiary alcohol e. b. secondary alcohol d. quaternary alcohol

none of these

29. In the carboxylic acids lab, we made the insoluble compound benzoic acid soluble in water by: a. gently heating it in water d. adding oil b. adding hydrochloric acid e. adding sodium hydroxide c. adding an emulsifier 30. Which of the following is soluble in water? a. methyl lineolate c. sodium lineolate b. lineolic acid d. none of these

e.

all of these

31. Which of the following properties is responsible for hexanes insolubility in water? a. molecular weight c. polarity e. size b. density d. boiling point 32. Which of the following acids is used in automobile batteries? a. nitric acid c. boric acid b. phosphoric acid d. sulfuric acid

e.

hydrochloric acid

33. A reducing sugar must contain which of the following functional groups? a. hemiacetal c. alcohol e. b. amide d. carboxylic acid

ester

34. While taking a melting point you observe your white crystals darkening. This is an indication that: a. a eutectic is forming b. your compound is starting to melt c. your compound is decomposing d. you are heating the Mel-Temp too rapidly e. your compound is impure

Exam A, Page 6 of 8

Organic Chemistry Laboratory Final Exam A

Chemistry 242 December 4, 2001

35. The Biuret test is very general for proteins. The reagent used for this test contained ________ ions which forms a violet color with proteins. a. Cu2+ c. Fe3+ e. Ca2+ b. Ni2+ d. -OH 36. The chromic acid test is a qualitative test to distinguish among primary, secondary, and tertiary alcohols. Chromic acid (H2CrO 4) is a powerful oxidizing agent. Which of the following statements is true? I. primary alcohols are oxidized to carboxylic acids II. secondary alcohols are oxidized to ketones III. tertiary alcohols are not oxidized by chromic acid a. none of these statements are true d. b. only I and II are true e. c. only III is true only I and III are true I, II, and III are true

37. The esterification reaction between a carboxylic acid and an alcohol occurs a. spontaneously d. only if the alcohol is primary b. in the presence of a strong acid e. only if the alcohol is secondary c. in the presence of a base 38. Fats are made up of a. phenols and glycerol b. glycerol and fatty acids c. phenols and fatty acids

d. e.

both b and c none of these

39. Which of the following statements about melting points is false? a. The rate of heating should be one or two degrees per minute. b. The amount of sample in the melting point capillary should be approximately 1-2 mm in height. c. Rapid heating results in a narrower melting point range. d. At a eutectic point, the melting point of a mixture has a sharp melting point. e. If a larger amount of sample is used, the melting point range may be broad. 40. A titration of 50 mL of an unknown concentration HCl solution required 8 mL of 0.2 M NaOH. What is the molarity of the HCl solution? a. 0.04 M c. 0.032 M e. none of these b. 40 M d. 31.25 M 41. Which of the following is an example of a disaccharide? a. starch c. glucose b. sucrose d. fructose

e.

none of these

Exam A, Page 7 of 8

Organic Chemistry Laboratory Final Exam A

Chemistry 242 December 4, 2001

42. Which of these reagents will not react with an alkene? a. aqueous potassium permanganate b. concentrated sulfuric acid in water c. concentrated sodium hydroxide in water d. bromine in carbon tetrachloride e. all of these react with alkanes 43. When carrying out the acetylation of salicylic acid, you first dissolved salicylic acid in acetic anhydride. Secondly you added 3 drops of phosphoric acid. What function did the phosphoric acid serve? a. the phosphoric acid aids in the solubilization process b. the phosphoric acid protonated the salicylic acid making it more reactive c. the phosphoric acid converted acetic anhydride to acetic acid which therefore would react more readily with salicylic acid d. phosphoric acid lengthened the reaction time, thus allowing for a better yield e. the phosphoric acid acted as a catalyst speeding up the reaction 44. The carbon tail of a typical soap contains: a. 6 to 12 carbon atoms b. exactly 12 carbons c. 12 to 36 carbon atoms d. at least 100 carbon atoms e. 12 to 18 carbon atoms 45. Which of the following species would give a positive ninhydrin test?
O CH3 C OH A H2N CH3 C H B COOH CH3 CH3 C H C D COOH CH3 O C CH3 CH3 CH3 C NH2 H E

a. b. c. d. e.

all five compounds would provide a positive ninhydrin test all except compound D would provide a positive ninhydrin test only compounds B and E would provide a positive ninhydrin test only compounds A and C would provide a positive ninhydrin test since D is the only ketone, it is the only compound that would provide a positive ninhydrin test

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