(4) (5) (6) a. b. H. explanation: explanation:
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1 ame Key 15 W11-Exam o. Page I. (15 points) For each of the following pairs of compounds, predict which compound is more acidic. Compare the two underlined s for each pair and circle the compound that is more acidic for each pair. The more acidic compound for each pair will be (circle one): (1) C C C C C () () C C (5) C () (6) II. (1 points) (a) Show the structures of the two possible conjugate acids of,-dimethylacetamide and explain, in several words, as to which of the two conjugate acids is more stable and would be expected to form preferentially. Use drawings of pertinent resonance form(s) and several words to explain your answer. C C C conjugate acids C C C C C C explanation: C C C C The positive charge in this conjugate acid structure is delocalized over the and atoms through resonance, thus the conjugate acid stabilized. C C (b) The pka value of the conjugate acid of DBU is considerably higher (~1) than that of a typical imine (estimated to be around 5-7). Explain this difference in pka values using resonance structures of the conjugate acids of both DBU and an imine.,-dimethylacetamide 1,8-diazabicyclo[5..0]- undec-7-ene (DBU) imine explanation: 1 The positive charge in the conjugate acid of DBU is stabilized by resonance. Therefore, this conjugate acid has a considerably higher pka (~1).
2 ame Key 15 W11-Exam o. Page III. (7 points) Glycoside 1 is a new iridoid glycoside isolated from the stems of edyotis hedyotidea, which have been used in traditional Chinese medicine [elv. Chhem. Acta 011, 9, 675]. Treatment of the glycoside, 1, with the enzyme β glycosidase provides disaccharide. Answer the following questions about this glycoside 1 and disaccharide. α 1 C enzyme (1) ( points) Label each of the glycosidic bonds in glycoside 1 using a small arrow ( ). () ( points) assify each glycosidic linkage in 1 as α or β right next to each of the arrows you have shown. () ( points) Is the hemi-acetal in disaccharide α or β? (circle one) α β (5) ( points) Is disaccharide a reducing sugar? (circle one) Yes o β A B (6) ( points) Describe the glycosidic linkage between the sugar units A and B [e.g., α(1 -> 6)]: α(1->6) (7) (1 points) Draw in the boxes the structures of the corresponding intermediate and the hydrolysis products. For the permethylated disaccharide, draw the structure using the aworth projection formula and for two hydrolyzed products of the permethylated glycoside, draw Fischer projections for the open-chain forms of the two carbohydrates produced. disaccharide (C ) S (excess) a (excess) (solvent) use Fischer projections use the aworth projection Sugar A Sugar B C C C C C C C C C C C C C C C C permethylated disaccharide 5 5
3 ame Key 15 W11-Exam o. Page IV. (5 points) Draw in the box provided the Fischer projection formula for ribose shown below. ribose C 5 V. (15 points) Treatment of triacetyl D-glucal () isopropyl alcohol in the presence of a catalytic amount of a strong acid results in the formation of an anomeric mixture of glycosides [see, e.g., Green Chem. 010, 1, 88]. Propose in the box below a step-by-step, curved-arrow reaction mechanism for this transformation from to. You may use -A and A- for the catalytic acid and its conjugate base, respectively. triacetyl D-glucal () A (catalytic) anomeric mixture Mechanism: A mech. arrows: pts interm. struc: pts mech. arrows: pts mech. arrows: pts interm. struc: pts mech. arrows: pts A interm. struc: pts 15
4 ame Key 15 W11-Exam o. Page 5 VI. ( points) Complete the following reaction schemes by providing in the boxes the structures of the corresponding intermediate and products. Make sure to indicate the stereochemistry where applicable. (1) [Synthesis 011, 1055] 1. aq K. (p ~ ) () (C C ) (C C ) () [rg. Lett. 011, 1, 109] S S C 1 1 S () [rg. Lett. 011, 1, 086] (C C ) (C C )
5 ame Key 15 W11-Exam o. Page 6 VII. ( points) Complete the following reaction schemes by providing in the boxes the structures of the corresponding intermediate and products. Make sure to indicate the stereochemistry where applicable. (1) [J. rg. Chem. 010, 75, 716] C aq K C C C () C aq K C C C () a tetrahydrofuran (TF; solvent) enolate a LDA tetrahydrofuran (TF; solvent) a Li dienolate [C(C ) ] I Br enantiomer () [rg. Lett. 011, 1, 015] a Li / Br I C 1. LDA (1.1 mol equiv) TF, -78 C. I C Li I [C(C ) ]
H CH 2 -OH (4) H b. (5) H H. (6) a. b.
ame Key 15 F010-Exam o. Page I. (15 points) For each of the following pairs of compounds, predict which compound is more acidic. Compare the two underlined s for each pair and circle the compound that
H CH 2 -OH (4) H b. H H (5) (6) a. b.
ame 215 F010-Exam o. 2 Page 2 I. (15 points) For each of the following pairs of compounds, predict which compound is more acidic. Compare the two underlined s for each pair and circle the compound that
O H HO H. !-D-galactopyranose
ame Key W06-Exam o. Page I. ( points) A disaccharide is cleaved by a β-glycosidase, an enzyme that specifically hydrolyzes a β- glycosidic linkage. When the disaccharide is treated with excess dimethyl
Structures in equilibrium at point A: Structures in equilibrium at point B: (ii) Structure at the isoelectric point: O O
ame 21 F10-Final Exam Page 2 I. (42 points) (1) (16 points) The titration curve for L-lysine is shown below. Provide (i) the main structures in equilibrium at each of points and B indicated below and (ii)
H H H OH OH H OH H O 1 CH 2 OH
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ame Key 15 W1-Exam o. Page I. (16 points) For each of the following pairs of compounds, predict which compound is more acidic. Compare the two underlined s for each pair and circle the compound that is
Structure at the isoelectric point: The predominant form of this tripeptide at ph 1 has a net charge of: (circle one)
ame Key 21 F07-Final exam Page 2 I. (1 points) Using the pka information given on page 12, match the following isoelectric point (pi) values (3.08, 6.00, and 10.76) to their corresponding amino acids by
Structures in equilibrium at point A: Structures in equilibrium at point B: (ii) Structure at the isoelectric point:
ame 21 F10-Final Exam Page 2 I. (42 points) (1) (16 points) The titration curve for L-lysine is shown below. Provide (i) the main structures in equilibrium at each of points A and B indicated below and
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