Organic Chemistry II - Midterm 2007

Organic Chemistry II - Midterm 2007 - CHM 2120 MIDTERM...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
CHM 2120 MIDTERM October 20, 2007 Name : ______ ANSWERS ________________________ Student Number : ______________________ Section: A (MRN Aud): ___________ B (MNT 203): ___________ Approximate total number of marks: 89 (subject to slight changes) Note: For questions in which mechanisms are not required, part marks might be given for incorrect answers with plausible mechanisms.
Background image of page 1

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

View Full DocumentRight Arrow Icon
CHM 2120 midterm - ANSWERS 2 of 9 1. Name the following molecules: (2 points) a. NO 2 Br 1-bromo-3- nitrobenzene or 3- bromo-1- nitrobenzene or m - bromonitrobenzene b. HO p -ethylphenol or 1-hydroxy-4-ethylbenzene Or 4-ethylphenol 2. Draw the structure of the following molecules: (2 points) a. m -chlorobenzoic acid CO 2 H Cl b. 6-phenyl-2-methylhexanoic acid 2 H CH 3 Ph 3. a. Which of the following molecules is most reactive and which is least reactive with Br 2 and FeBr 3 ? (2 points) O 2 N O O O Me O O O 2 N AB C D E Most reactive: ________ C ___________ Least reactive: ________ D __________ b. Give the expected product from the reaction with compound C . (2 points) O Me Br O Me Br 1 2
Background image of page 2
CHM 2120 midterm - ANSWERS 3 of 9 4. a. Give a detailed mechanism for the formation of the major product in the following reaction including the key resonance structures involved: ( 8 pts ) b. Clearly explain (using structures primarily) the reason for the formation of the major product ( 6 pts ) c. Name the key intermediate formed in this reaction (1 point) σ -complex or arenium ion 1 1 O EtCl AlCl 3 CH 3 3 Cl AlCl 3 O 3 3 H H H H O CH 3 3 H H +ortho same resonance structures as para, but the o r t h o s u b s t i t u t i o n i s b l o c k e d b y s t e r i c h i n d r a n c e with the i -propoxy subsituent O 3 3 H H σ -complex is stabilized by resonance with the π bonds A N D b y r e s o n a n c e w i t h t h e o x y g e n l o n e p a i r s .
Background image of page 3

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

View Full DocumentRight Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 01/16/2011 for the course CHM 2120 taught by Professor Dr.flynn during the Fall '10 term at University of Ottawa.

Page1 / 10

Organic Chemistry II - Midterm 2007 - CHM 2120 MIDTERM...

This preview shows document pages 1 - 4. Sign up to view the full document.

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