2OB3 - Summer 2006 - Tutorial 1

2OB3 - Summer 2006 - Tutorial 1 - the structure of the sex...

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1 Summer 2006 P.M. Zelisko Chemistry 2OB3 Tutorial 1 1. Fill in the necessary reagent(s) or product(s) to complete the following reaction schemes: O OEt OH F 3 C (a) (b) H 2 , Pd/C (c) + Br 2 (xs)
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2 2. Classify the following molecules as aromatic, antiaromatic, or non-aromatic. O O N H N - -
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3 3. The sex attractant of the fall armyworm moth is produced by the female. This material, which attracts the male moth at very low concentrations, is called spodoptol and is a primary alcohol with the molecular formula C 14 H 28 O. Hydrogenation of this alcohol gives 1-tetradecanol, C 14 H 30 O. Ozonolysis of spodoptol is known to give two aldehydes, aldehyde A (C 5 H 10 O) and aldehyde B (C 9 H 18 O 2 ), indicating the position of the double bond in spodoptol. At this point
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Unformatted text preview: the structure of the sex attractant is known, except for the stereochemistry of the double bond. So little of the material is isolated from the female moths that the compound had to be synthesized before the stereochemistry could be determined. (a) Draw the structures of the compounds formed in the following synthesis of spodoptol. O H NaNH 3 (excess) NH 3 (liquid) 1. bromobutane (1 equiv.) 2. H 3 O + H 2 catalyst spodoptol (b) Assign the structure of the two aldehydes formed after the following reaction: spodoptol 1. O 3 2. H 3 CSCH 3 C 5 H 10 O C 9 H 18 O 2 4 4. List the following in order of increasing acidity: (1 = least acidic) OH OH Cl OH OH Br Br Br...
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This note was uploaded on 05/18/2011 for the course CHEM BIO 2a03 taught by Professor Gullon during the Winter '10 term at McMaster University.

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2OB3 - Summer 2006 - Tutorial 1 - the structure of the sex...

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