WS3-W08 - CH 3 Br CH 3 OH + enantiomer b) Convert your...

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Chem 51B - Jarvo Worksheet 3 1. Provide an arrow-pushing mechanism for the following reaction. Ignore stereochemistry. Your answer must be neat and clear . HBr heat OH CH 3 CH 3 H 3 C H 3 C CH 3 Br H 3 C 2. Predict the major product and provide an arrow-pushing mechanism. CH 3 H 2 SO 4 H 2 O 3. Fill in the boxes with the appropriate starting material, reagent or major product. Show stereochemistry where appropriate. Where indicated, fill in the reaction mechanism. H 3 C H 3 C H 3 C H 3 C CH 3 OH + H 3 C H 3 C CH 3 OH H 3 C H 3 C H 3 C H 3 C OH CH 3 NaNH 2 (2 equivalents) DMSO Mechanism: Br 2 CH 3 CH 3
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Chem 51B - Jarvo Br 2 (2 equiv.) H 2 SO 4 H 2 O CH 3 CH 3 1. BH 3 2. KOH, H 2 O 2 CH 3 CH 3 H + NaNH 2 Br O H + NaNH 2 O
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Chem 51B - Jarvo 4. Rank the following : a) Most to least stable carbocation: H OCH 3 H 3 C A B C H CH 3 H 3 C H H H 3 C b) Fastest to slowest reaction with aqueous H 2 SO 4 H 3 C H 3 C CH 3 H 3 C A B C CH 3 CH 3 CH 3 c) Weakest to strongest base: A B C NaNH 2 NaH NaOCH 3 Bonus: Label each base with the pK a of its conjugate acid. 5. Convert the following synthetic scheme to a retrosynthesis: H 3 C H 3 C H 3 C H 3 C Br Br H 3 C H 3 C + enantiomer
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Chem 51B - Jarvo 6. a) Fill in the retrosynthesis with the appropriate compound.
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Unformatted text preview: CH 3 Br CH 3 OH + enantiomer b) Convert your retrosynthesis to a synthetic scheme (forward direction), and include the appropriate reagents. R e a g e n t s : R e a g e n t s : 7. Complete the retrosyntheses below. a) Fill in the retrosynthesis with the appropriate compound. H 3 C H 3 C Br OH + enantiomer b) Fill in the retrosynthesis with the appropriate compound B and reagents. C A B Reagents: Reagents: CH 3 H H CH 3 Chem 51B - Jarvo c). Fill in the retrosynthesis with appropriate compounds B and A and reagents. B Reagents: Reagents: O CH 3 H O H CH 3 CH 3 H 3 C H H I CH 3 O H OH CH 3 Me A C Possible organic Starting Materials and reagents. All carbons in C must come from one of the following compounds. You may use as many as you want, in any order you want. You can also use any inorganic reagent that you wish....
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WS3-W08 - CH 3 Br CH 3 OH + enantiomer b) Convert your...

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