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1.* Draw a diastereomer of

OC[C@H](O)[C@H](O)C=O or OC[C@@H](O)[C@@H](O)C=O

2.

OCC(O)C(=NNc1ccccc1)C=NNc2ccccc2

8. How many D-aldohexoses yield optically active aldaric acids? 6

9. Select the structure that is the same as the structure in the box:

10. The disaccharide is called

A. 1-O-(b-D-glucopyranosyl)-b-D-glucopyranose

Examine the following structures and then answer questions 11-14.

11. How many of the compounds will mutarotate? 1 Compound C is a hemiacetal.

12. How many of the compounds are ketals? 1 Compound B

13. How many of the compounds contain a 1,4-glycosidic bond? 0

14. Enter the letter of any compound that contains a 1,3-glycosidic bond. Enter N if none of them contains a 1,3-glycosidic bond. N

15. Maltose is a disaccharide that exists as two anomers. The a-anomer has a specific rotation of +168^o, while that of the b-anomer is +112^o. At equilibrium the mixture has a specific rotation of +136^o. What is the percentage of the a-anomer present in the mixture at equilibrium? Enter your answer to 3 significant figures. Do not include a % sign. 42.9

16. A chemist isolated a ketopentose with the molecular formula C₅H₁₀O₅ from the cell walls of a plant. When he treated this material with NaBH₄ in aqueous methanol, the resulting product was optically active. Was the compound a member of the D family of sugars or the L family? Enter the letter D or L. D or L was acceptable.

17. If is alpha-(D)-glucopyranose, then is named....beta-(D)-galactopyranose.

18. and is named.....alpha-(L)-glucopyranose This compound is the mirror image of the one above it.

19. Draw the structure of A, the product of the follwing reaction:CC1(C)OC2C(O)OC(CO)C2O1

20. Draw the structure of B, the product of the following reaction:COCC1OC(OC)C2OC(C)(C)OC12

21. Specify the stereochemistry at each chiral center in b-(D)-glucopyranose. Enter your R/S designation for each chiral center in order, starting with C-1. RRSSR

22. Select the alkene that would undergo acid catalysed hydration fastest:

23. CC(=O)OC(c1ccccc1)c2ccccc2

Consider the dehydrobromination of 1-phenyl-2-bromobutane, then answer question 24-27.

24. If the product mixture contains 45% C, 25% D, and 30% E, how many of the following statements about this reaction are justified by the data? 2 Statements B and E are justified. The reaction is not thermodynamically controlled since compound D, which is thermodynamically the most stable is formed in lowest amount.

A. It is thermodynamically controlled.

B. It is regioselective.

C. It is both thermodynamically and kinetically controlled.

D. Compound E is more stable than compound D.

E. Tertiary hydrogens are more reactive than primary hydrogens.

25.* If the product mixture contains C and E, but no D, draw the structure of the stereoisomer of the starting material that was used in the reaction. or its mirror image: C[C@@H](Br)[C@@H](C)c1ccccc1 or C[C@H](Br)[C@H](C)c1ccccc1

26. If the product mixture were treated with aqueous acid, which compound would react the fastest? Enter the letter that corresponds to the structure you select. C Compounds C and D should both be more reative than E because protonation of C and D produces a tertiary carbocation, while protonation of E generates a secondary cation. Protonation of C and D generates the same intermediate. Since D is more stable than C, the energy difference between D and the transition state leading to the intermediate must be greater than the energy difference leading from C to the transition state. Hence, C reacts fastest.

27. Consider the following reaction sequence:The ¹³C-NMR spectra of compounds F and I are shown below. Draw the structure of compound F.

CC1CCCCC1=O

28.ClC1CC2CC1C=C

29. In the reaction, , draw the structure of J, assuming that the bond indicated in red has undergone the sigmatropic rearrangement.

CC12CC2C=CC=C1

30. Consider the following symmetry allowed reaction: . What is the number of the carbon atom that the arrow is pointing to in the product?