W02 midterm2b key

W02 midterm2b key - ORGANIC CHEMISTRY 308 Winter 2002...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: ORGANIC CHEMISTRY 308 Winter 2002 MIDTERM EXAM II (PINK) On my honor, I have neither given nor received any aid on this examination NAME (use ink please) LAST FIRST MIDDLE SIGNATURE (use ink please) TA (circle name): Jennifer Becky Martha Ryan Adam Problem Points 1 (12) 2 (8) 3 (42) 4 (11) 5 (27) Hill TOTAL / 100 Bonnus (10) (EXTRA CREDIT) ONLYEXAMS WRITTEN IN INK WILL BE CONSIDERED FOR REGRADING page 1/7 Names, Structure and Theory 1) Please draw the line—wedge-dashed line structures that correspond to the following names: (a) (4 Points) cis-3-acetyl-1—methoxycyclohexane OM ‘ (b) (4 Points) 2,5—diethynyl-2,5-dimethylpentane M (c) (4 Points) 4,4-dimethyl-5-hexene-3—one W O 2) (2 points each) Circle the structure in each of the following sets which has highlighted the most acidic hydrogen. 3) (42 points, 7 each). Please draw the structures of the expected product(s) in the following single- step transformations showing all the correct regio- and stereoisomers (please do not write +enantiomer, unless an enantiomer is expected). K2CF207 W 1 w W OH OH W L H3CJIOOH w M H’ O 532% O : Na° (excess) Ex: r6 NHa (liq) ~_. 0 \/ SOCIZ H/ Pyridine ; U MeCH=P( Ph)3 \ \K / page 3/7 4) (l 1 Points) Using correct arrow pushing conventions, please propose a mechanism for the following reaction. Please indiacte MeOH;+ as the proton donor and MeOH as the proton acceptor HINT: The product is shown in parenthesis in a conformation that should be easy to relate to the ractant. Please draw neatly. 01A, page4/7 5) (27 points ) Please draw inside the box the correct structure ofthe products or reagents that correspond to each step in the following transformations (3 pts per correct answer). Wa'Bv E? H 9'0 ~ Ether 1000C t ax m0 mew‘a‘xbw :— SWAG" QOLQ)‘ Na 1 NH; (1) /\/\ mum Imuluu - \ n CH3SOZCI 0 g page5/7 KO H EIOH page6/7 9 (9 H 3C‘PP h3 It ’I + Enantiomer all. Extra Credit (10 Points): Please draw the structure obtained afier each of the following reactions to justify the formation of the final product. u/lkfiflcat) 2) NaNH2 3)O_“\\‘ ,HgO \\ W QH 4) H2. BaCO3(Lindl ar) “ o 1' 5) BC] cat. /THF 94% 1) 2) 4) 24“ 5) A O \/< page7/7 THIS IS AN EMPTY PAGE page 8/7 ...
View Full Document

Page1 / 8

W02 midterm2b key - ORGANIC CHEMISTRY 308 Winter 2002...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online