R or S? 2) oxidation numbers of the designated carbon atoms: note: An oxidation number must have a sign. F 3 C OCH 3 oxidation #: OH.
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1 ame Key 5 0-Exam o. Page. ( points) The following compounds are those used in our study on the mechanism of the chemical carcinogenesis of benzo[a]pyrene. ) esignate in each of the boxes below the stereochemistry ( or ) at the indicate carbon center and ) provide in each of the boxes provided the formal oxidation number of each of the indicated carbon atoms. ) stereochemistry ( or ) of the designated carbon centers: or? or? or? C C C C or? or? ) oxidation numbers of the designated carbon atoms: note: n oxidation number must have a sign. - C C. (0 points) Write in the boxes below the expected hybridization of each of the indicated atoms (i.e., sp, sp, or sp) in the following molecules. sp C sp sp C sp sp C
2 ame Key 5 0-Exam o. Page. (0 points) The two-step wern oxidation of a secondary alcohol provides the corresponding ketone as shown below. The intermediate produced after step is a sulfoxonium ion. Treatment of the sulfoxonium ion with a bulky base (step ) results in the formation of the ketone.. C C When mono-deuterated cyclohexanol is subjected to dioxalyl chloride and dimethyl sulfoxide (i.e., step above), mono-deutrated sulfoxonium ion is produced. This then undergoes oxidation upon treatment with triethylamine [(C C ) ] and the label ends up in dimethyl sulfide as shown below. C C. C C n the basis of the information given above, propose in the box below a step-by-step, curved-arrow mechanism for the formation of cyclohexanone () from the sulfoxonium ion intermediate (). C C (C C ) arrows: points C C structure: points; arrows: points C C V. (0 points) n the box below, write a step-by step, curved-arrow mechanism for the following reaction [J. rg. Chem. 00, 75, 69]. C C C C C * 0 *ften drawn as: Mechanism: C C C arrows: points C C C C structure: points; arrows: points C C 0
3 emember Lone pair-assisted ionization. ame Key 5 0-Exam o. Page V. ( points) [Eur. J. rg. Chem. 00, 65] Treatment of diol with acetal 5 in the presence of a catalytic amount of p-toluenesulfonic acid (Ts; pka -0.5) results in the formation of a new acetal, 6, shown below. raw the structure of the expected uncharged acetal intermediate in the designated box below and propose in the box below a step-by-step, curved-arrow reaction mechanism for this transformation from the diol to acetal 6. You may use - and - for the acid Ts and its conjugate base, respectively. You do not need to balance each step. C C C ote: = C (i) raw the mechanism through the formation of the uncharged acetal intermediate. 5 C C C C C (ii) raw the mechanism through the formation of the acetal product, 6. each intermediate structure: points each set of mech. arrows: point C C uncharged acetal intermediate C acetal product (6)
4 ame Key 5 0-Exam o. Page 5 V. ( points) Complete the following reaction sequences by providing in each of the boxes the structure of the corresponding starting compound or product. f more than one stereoisomer would be formed for a product, draw one of the stereoisomers and write enantiomer or diastereomer in the box. () [ucleosides, ucleotides and ucleic cids 00, 9, 6] (MCPB) a a () [J. rg. Chem. 00, 75, 6] C 6 6. C Mg. aq K (acidic) Δ (heat) C 7 8 s (mol equiv) enantiomer () [ynlett 00, ] C C a C C a
5 ame Key 5 0-Exam o. Page 6 V. ( points) Complete the following reaction sequences by providing in each of the boxes the structure of the corresponding starting intermediate or product. f more than one stereoisomer would be formed for a product, draw one of the stereoisomers and write enantiomer or diastereomer in the box. () C C two stereoisomeric bromonium ion intermediates C C or C C 7,-trans diaxial () [ynlett 00, 6] C () [ynthesis 00, ] PCC (C C ) C C C () [rg. Lett. 00,, 07] Ts,, ( C) C=
R or S? 2) oxidation numbers of the designated carbon atoms: note: An oxidation number must have a sign. F 3 C OCH 3 oxidation #: OH.
ame 5 F0-Exam o. Page I. ( points) The following compounds are those used in our study on the mechanism of the chemical carcinogenesis of benzo[a]pyrene. ) Designate in each of the boxes below the stereochemistry
R or S? oxidation #: hybridization:
Remember Lone pair-assisted ionization. ame 15 F07-Exam o. 1 Page I. (0 points) The following compounds are those used in our study on the enzymatic transformation of cholesterol to pregnenolone. 1) Designate
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)
C C H 2. O p-tsoh (catalytic) H 3 O +! O
ame Key 15 W06-Exam o. Page I. ( points) Pheromones are those chemicals that play a role in communication between individual animals or insects. Structure 1 is the pheromone of the Japanese peach moth
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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
(5) a. b. (6) N H CH 3 N H O H O (7) CH 3 O (8) OCH 3 2. explanation:
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
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
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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hemistry 10 First ame Final Examination Last ame h; 0 points please print clearly Dr. Kathleen olta ignature UM ID # PRIT TE FIRT LETTER F YUR LAT AME ERE: Problem Points core GI I II III 0 IV V 1 VI 0
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