1 2009TEst1A_2204-6-8 answers - ( R )-5-fluoro-2-nonanone :...

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Chemistry 2204/6/8 (’09) Test 1A Name: Marks are in parentheses 1 .(15) Name the top 12 reactions of carbonyl containing compounds and give an example of each using prototypical compounds and reagents. Note: 3 reactions are subdivided into two subcategories. SEE NOTES 2 .(4) For each of the molecules shown below, circle and name at least 2 functional groups. aldehyde amide acetal ether diene phenol 3a (4) Indicate, with an arrow, the most acidic site(s) on the ketone shown below. Draw the corresponding enol tautomer . Calculate the degree of unsaturation – show the details of your calculation. O enol deg unsat = OH [(2n +2 ) - Obs #H]/2 =[16-14]/2 = 1 3b (1) Rank the following 3 molecules with respect to oxidation state. (1) highest (3) lowest 2 OH O O H 1 4a (2) Name the following molecule. Include stereochemical information. O H 4Z-hexenal 4b (2) Draw the correct structure for the following molecule. Show stereochemical details.
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Unformatted text preview: ( R )-5-fluoro-2-nonanone : O F 1 2 3 1 Chemistry 2204/6/8 (08) Test 1A Page 2. 5 (10) Supply the missing reagent, starting material or product for each of the following reaction. O HO HCN-CN O H 3 CO O H + CH 2-PPh 3 C N N R R + CH 3 OH + H 2 O + O-PPh 3 O Cl Cl Cl H 2 O H 2 O + O OH H : O HNR 2 H+ OH Cl Cl Cl OH 6 (7) MECHANISM: Draw a mechanism for the following reaction, showing all 5 intermediates, all curly arrows describing electron movement and all charges (if applicable). Hint: PLATLD! O MeO H 2 O + H + HO O H + MeOH O MeO H HO O H HO O H Me OH 2 HO MeO H OH 2 HO HOMe H OH HO HO H 7 (5) SYNTHESIS: Supply the missing intermediates (2) and reaction conditions (3) in the synthesis of raspberry ketone from parahydroxybenzaldehyde and acetone. O HO O HO O O HO O HO OH ALDOL Dehydration Hydrogenation 2 3...
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This note was uploaded on 07/28/2009 for the course ORGANIC CH CHEM 2204 taught by Professor Dr.levin during the Winter '08 term at Indian Institute of Technology, Chennai.

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1 2009TEst1A_2204-6-8 answers - ( R )-5-fluoro-2-nonanone :...

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