Exam 3 key

Exam 3 key - H 16 O C 17 H 19 DO 2 (sorry!!) O H 1) CH 3 CH...

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CHE 3332 Exam 3 1) Fill in the boxes with possible starting materials, reagents, or major organic products (as appropriate): Name___________________ Row_____ C 9 H 18 O 3 open chain dihydroxy ketone H 3 O + O O CH 3 CH 3 CH 2 CH 3 Cl H OH H CH 3 NaOH C 4 H 8 O - show stereochemistry!! NaSCH 3 C 5 H 12 OS - show stereochemistry!! O O 1) CH 3 CH 2 Li (excess) 2) H 3 O + (mild) OH OH name??? name??? (E)- 2-butenal OH C 4 H 8 O NaBH 4 H 2 O *note - the carbon with 2 oxygens is always the oned that becomes a carbonyl OH OH CH 3 CH 3 CH 2 O CH 3 O OH OH Homework #17.34c (p744) General rxn bottom p720 S N 2 O O H 3 C H CH 3 H S N 2 OH H 3 C H CH 3 H H 3 CS Homework #16.34c (p695) General rxn p675 (16.10) General rxn p677 (16.12) (5R)-1,5-hexanediol reduction of ester gives 1° alcohol from carbonyl + a second alcohol section 15.3 p626 a) LiAlH 4 b) H 3 O + or NaBH 4 , ROH or H 2 O 3° alcohol from organometallics adding 2 times to carbonyl OH OH CH 2 CH 3 CH 2 CH 3 OH HO Section 14.10 OH O H Section 15.10 p638 PCC or PDC no acid/water! Section 15.2 p622
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OH O HO H + (catalytic) an ether; C 7
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Unformatted text preview: H 16 O C 17 H 19 DO 2 (sorry!!) O H 1) CH 3 CH 2 MgCl, THF 2) H 2 SO 4 , heat (-H 2 O; E1) 3) CH 3 OH, H 2 SO 4 (cat) O 1) Br 2 , FeBr 3 (para isomer only) 2) excess CH 3 OH; H + (catalytic) 2) Mg, diethyl ether 3) D 3 O + , low temp K 2 Cr 2 O 7 H 2 SO 4 O HCl (excess) H 2 SO 4 (-H 2 O) LDA (excess) C 6 H 10 HO OH Section 15.7 Section 16.5 (see example bottom p634) Cl Cl Section 16.8 (see problem 16.10 p673) Old Stuff (E2 elimination; 1° RX + hindered strong base) O OCH 3 Section 16.5 p668 (acid cat ether formation) (last exam) O O Section 15.8 p635 (Fischer esterification) CO 2 H CO 2 H Section 15.10 p638 (ox. of 1° alcohol) Section 11.13 p438 (ox. of benzylic carbon) D OCH 3 CH 3 O (last exam) acetal formation (17.8) Grignard formation followed by acid (deuterium)...
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This note was uploaded on 04/14/2008 for the course CHE 3332 taught by Professor Primrose during the Spring '08 term at Baylor.

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Exam 3 key - H 16 O C 17 H 19 DO 2 (sorry!!) O H 1) CH 3 CH...

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