CHE 102 Exam 3 CH 3 CHCOOH. CH 3 CH 2 CH 2 O d. e. f. CH3 COO g. h. i. O O CH 3 CCH 2 CCH 3

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1 CE 102 Exam 3 1. (1 pt each) Classify the following molecules as aldehydes, ketones, carboxylic acids, or esters: a. b. c. C C 3 CC C 2 C 2 CC 3 C 3 C 2 C 2 d. e. f. CCC 3 C 3 C 3 CC 2 C 2 C C3 C g. h. i. ClC C 3 CC 2 CC 3 CC 2 CC 3 2. (2 pts each) Name the molecules in Question 1. a. b. c. d. e. f. g. h. i.

2 3. (1 pt each) For the compounds a, b, c, and d in question 1, indicate if the compound is chiral or achiral. If chiral, give the locator number of each chiral carbon in the molecule. a. b. c. d. 4. (1 pt each) In each pair, circle the compound which is more soluble in water and explain why: acetic acid; methyl formate propanal; methanal 5. (1 pt each) In each pair, circle the compound which has the higher boiling point and explain why: ethyl formate; propanal propanone; 2-propanol 6. (2 pts each) Draw the products of the following reactions: a. C + C 3 + Δ b. C + 2 Ag +

3 c. Cl 3 CC d. Cl 3 CC + 2 C (4 pts each) Give reactants and any necessary reaction conditions to form the following: a. C 3 CC 2 C 3 b. C 2 Cl c. C 3 C 2 C - Na + + BrC 2

4 8. (18 pts) Vigamox, an anti-infective solution used for the eyes, is shown below. Circle and label the functional groups in Vigamox. I have already done so for one group. Cl F N N N C 3

5 9. (6 pts) List the following compounds in order of decreasing solubility in water and justify the order you chose by listing the strongest force for each: diethyl ether, pentane, 1-butanol, N-methylethanamide, propanoic acid, methylpropylamine. 10. (4 pt) There is concern that a manmade toxin used as a flame retardant in television sets and plastic toys has been found in the Arctic food chain. There is evidence that this toxin molecule, decabromodiphenyl ether (deca-bde), breaks down to even more toxic penta- and octa-bdes. Draw the structure of decabromodiphenyl ether. 11. (1 pt each) In each pair, circle the compound which has the higher boiling point: butanamide; butanamine trimethylamine; propylamine 1-butanol; methyl ethyl ketone 1-bromobutane; butanoic acid

6 12. (3 pts each) Classify each of the following as primary, secondary or tertiary amines or amides: a. b. c. C 2 C 3 C 3 NC 2 C 3 C 3 CNC 3 N d. e. f. NC 3 C 3 C 2 CC 3 C 3 C 2 CN 2 N (3 pts each) Draw the structures of the named compounds: a. 3-ethyl-2-methylhexane b. trans-2-pentene c. 2,4-dibromophenol d. 2-methylcyclohexanone e. ethyl butanoate f. 3-amino-2-hexanol 14. (3 pts each) Write the names of the following compounds:

7 a. b. C 3 Cl C 3 C 3 CC 2 CC 3 c. d. C 3 CC 2 C 2 C CC 2 S e. f. C 3 CNC 2 C 2 C 2 C 3 C 3 CC 2 C 2 C C Ascorbic acid (vitamin C) is a carbohydrate derivative. Its unusual structure and function (which we will discuss in a later chapter) derives from the enediol grouping near the top of the molecule.

8 C 2 a. (2 pts.) ow many chiral carbons does ascorbic acid have? b. (5 pts.) This molecule is soluble in water, somewhat soluble in ethanol and insoluble in benzene or chloroform (C 3 Cl). Is ascorbic acid polar, non-polar or slightly polar? Use the solubility information to back up your answer. 16. The monosaccharide D-tagatose has the following open-chain structure: C 2 C 2 a. (2 pts.) Classify this sugar according to the number of carbons it has. b (2 pts.) Classify this sugar according to its functional groups. c. (2 pts.) Circle one: this sugar is the D-stereoisomer the L-stereoisomer achiral (not chiral) d. (2 pts.) True or false: this sugar is predicted to rotate light in the + direction.

9 e. (6 pts.) Draw the aworth structure of this monosaccharide. To start you off, I ve drawn the skeletal structure for you; all you have to do is to fill in all eight atoms or groups that attach to the top and bottom of the vertical bars. f. (4 pts.) Draw the Fischer projection of the open-chain structure of the product of the reduction of D-tagatose. int: Note that D-tagatose s carbon 1 is not likely to be reduced. (extra credit 3 pts.) Note that the molecule you ve drawn above is no longer a saccharide since it lacks unsaturation. Name the molecule you ve drawn using IUPAC nomenclature rules.

10 17. Trehalose is a disaccharide found in honey; its crystalline form is prized by bakers because it does not brown as readily as other disaccharides such as sucrose or maltose. C 2 C 2 a. (4 pts.) Describe the glycosidic bond (linkage) between the two monosaccharide units in trehalose. int: Be careful about how you number the carbons, especially in the right-side monosaccharide. Include the α, β notation, if appropriate. 18. (6 points) Draw the structure of a component of beeswax that contains myricyl alcohol (formula: C 3 (C 2 ) 12 ) and palmitic acid (formula: C 3 (C 2 ) 14 C).

11 19. Given a lipid bilayer, answer the following questions: a. (2 points) Which of the following is more likely to be found in the middle of the bilayer? sphingomyelin choline b. (4 points) Explain how you arrived at your answer.