Organic Chemistry 2 - Final_2007_ANSWERS

Organic Chemistry 2 - Final_2007_ANSWERS - CHM 2120 Final...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
CHM 2120 Final Exam – ANSWERS December 2007 Alison Flynn Time: 3 hours Name: ____________________________________________ Student Number: ___________________________ Circle your section : A (MRN) or B (MNT) Notes: - Attempt all questions - The final 2 pages contain a periodic table, a table of IR stretching frequencies, and a table of 1 H NMR chemical shifts. These pages may be detached. - A calculator, ruler, and molecular models are permitted - Where possible, draw structures to prove your point - Show relative stereochemistry where applicable - Total number of pages: 14 - Approximate number of points: 107 o The marks are given as a guide and are subject to minor changes GOOD LUCK!
Background image of page 1

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

View Full DocumentRight Arrow Icon
Answers 2 of 14 1. Name the following molecules using IUPAC nomenclature or accepted trivial names: (2 points) a. Cl 1,3-dichlorobenzene or m -dichlorobenzene b. N H Ph O N -phenyl-2,2-dimethylhexanamide 2. Draw clear structures for the following molecules: (2 points) a. ( Z )-but-2-enal O H b. Methyl 2-hydroxybutanoate O O OH 3. a. Write equations for the following reaction using arrow notation. (2 points) b. Will the reaction favour the starting materials or the products? (1 point) c. Justify your choice. (3 points) O O O + H O O OH base conjugate base - Compare the base and the conjugate base - Both have a negative charge on oxygen, but the conjugate base is resonance-stabilized, while the base is not. - The conjugate base is therefore more stable than the base, and the equilibrium favours the weaker/more stable side, i.e. the products.
Background image of page 2
Answers 3 of 14 4. Rank the following molecules in increasing order of reactivity with H 2 NEt. (3 points) Cl O O O O OMe O NHMe O ABC D ____ D ____ < ___ A ______ < ____ C _____ < ____ B ______ 5. The following reaction won’t work as shown: OH O N H N O a. Show what would happen instead. (2 points) O O N H N O H O O N H H b. How could you obtain the desired product? Show the reagents to be used and the structures of any intermediates. (3 points) O O N H N O H SOCl 2 O This route works best: 2 equivalents, or add a non-nucleophilic base like Et3N An accepted answer: O O H H + ,HOMe (or another alcohol) OMe O N H N O
Background image of page 3

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

View Full DocumentRight Arrow Icon
Answers 4 of 14 6.
Background image of page 4
Image of page 5
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 / 14

Organic Chemistry 2 - Final_2007_ANSWERS - CHM 2120 Final...

This preview shows document pages 1 - 5. Sign up to view the full document.

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