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Chem634_F11_Final_Key - Initials Chemistry 634 Fall 201 1...

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Unformatted text preview: Initials Chemistry 634, Fall 201 1 Final Exam Prof. Donald Watson 300 points (3 hours) 0 Closed note, closed book. No calculators allowed. You may use a molecular model set. ' Answers should be written in boxes provided. Other markings will not be considered. Scratch paper can be found at the back of the exam packet. 0 Please initial each page at the top. - Points will only be awarded for clearly‘conjmunicated answers. ° Please make sure you have all pages of the exam packet (12 pages). Name [402 Question 1: /25 Question 2: /23 Question 3: _/32 Question 4: ____/20 Question 5: I40 Question 6: I40 Question 7: I40 Question 8: I40 Question 9: ___/40 Total: [300 Page 1/12 Initials 1) (25 points, 5 points each) Predict the expected major product for each reaction sequence after aqueous work—up, drawing your answer in box provided. Denote stereochemistry where needed. If no reaction is expected, state so. 1) TsNHNH, 2) Hanson. rson O U —* l-Bu o 0 glfiDgchenMel oJlxNJVEI ) a ‘ Lg Bn Li{sBu)33H _l25 points Page 2/12 lnitials 2) (23 points) In the spaces below, provide the missing reagents and intermediates needed to complete the synthesis. Note: More than one step or reagent may be required over each arrow. TBOPSO 1) 03. then OMS 2) BUUJ. 0 °C a o —.-_. l “V 0 f _ JI oan PPhs 3: Me Ph a, u. 5 1 l23 points 3) (32 points) in the spaces below, provide the missing reagents and intermediates needed to complete the synthesis. Note: More than one step or reagent may be required over each arrow. ii)?” Ci CI OMAR 125 °C __, v’i 90""?“4‘i A “abode / amid-ans 1),”! Initials 4) (20 Points) Referring to the Scheme shown in Question 3, in the space below, please provide a detailed mechanism for the conversion of 2 to 3, and rationalize the observed stereochemistry. [20 points Page 4/12 Initials 5) (40 points) in the space below, please provide a detailed mechanism for the reaction shown that accounts both for the connectivity and stereochemistry of the product. 0 OH ”0+9” THIS 1 8 Ti P L 53:53.3) I ”N8 HRH/kph was J one”; P“ M8 Me PWM Aoi‘ct! I40 points Page 5/ 12 Initials 6) (40 Points) A) Please provide a mechanism for the transformation shown below. For now, you can ignore stereochemistry. unprsypn, ?|P(S)Phg Megs/\fo‘s‘ a, ’ 0 0H K2C03 B) Using Newman Projections, in the space below please provide a reasonable model to account for the stereoselectivity in the transformation shown in question 6a. Six {rt-at Neva... Projafi‘flfl‘ ‘ M s. (Md 6A6?) Alp”; {1) be, to,“ A” g—sfl‘, W OMLf 9(975 l " “‘1. gm... N 0+9 (/g‘ _/40 mints argonalvh Mgr»: Mon-1'3 a [$0 ark/9H. Page 6/12 Initials 7) (40 Points) A) Please provide a complete mechanism for the transformation shown below. For now, you can ignore stereochemistry. pn OH 0 u PhCHO. tE-uOK. 0 °C, 3h o’ko o 2) OIBAL then H30* MeWOEi ——————> Me\}\)\)LH B) In the space below please provide a reasonable model to account for the stereoselectivity in the transformation shown in question 7a. __/40 points Page 7/12 Initials 8) (40 points) Using a maximum of 5 steps, propose a synthesis of 5 using the given starting material 4 and any other commercial or readily accessible reagents. I40 points Page 8/19 _ Initials 9) (40 points) Using a maximum of 5 steps, propose a synthesis of 7 using the given starting material 6 and any other commercial or readily accessible reagents. Mo NH2 N o I 6 / 7 I40 points Page 9/ l 2 ...
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