s20 2011 week 2 day 4 - post

s20 2011 week 2 day 4 - post - R and S Nomenclature...

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H H H Cl O N HO H 3 C OH H R and S Nomenclature 1. Circle all the stereocenters in the following molecules. For each stereocenter, assign an R or S designation according to the standard rules. 2. Draw an unambiguous structural representation of the following molecules: ( S )-4,5-dimethyl-( Z )-2-hexene ( R )-3,5,6-trimethyl-( E )-3-heptene 3. Provide the best possible systematic name for the following compound: Chemistry S-20ab Week 2 49 R S S S S S R R R (S,E)-5-isopropyl-2,3,7-trimethyloct-4-ene (S,E)-5-isopropyl-2,3,7-trimethyl-4-octene OR
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More Stereochemistry of Alkene Additions 1. Fill in each box with the starting materials that would lead to the indicated product. Be sure to indicate the correct stereochemistry. 1. BH 3 ,THF 2. H 2 O 2 ,NaOH Br 2 Chemistry S-20ab Week 2 57 D 2 Pd/C Br 2 Br Br OH D D (+/-) (+/-) O Br Et Me (+/-) HO
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Cyclohexanes 2. Draw each of the following dimethyl cyclohexanes (on the planar ring), then identify whether the substituents would be either: "Axial and Equatorial" or "Both Equatorial" 1,2-cis 1,3-cis 1,4-cis 1,2-trans 1,3-trans 1,4-trans 3. Draw each of the following in the most stable chair conformation: 1. Look at the chair drawn below. Notice the axial and equatorial substituents. Pay close attention to the parallel lines! Chemistry S-20ab Week 2 58 Axial & Equatorial Axial & Equatorial Axial & Equatorial Both Equatorial Both Equatorial Both Equatorial
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Nucleophilic Substitution: The S N 2 Reaction Can you predict the product and the mechanism of the following reaction: Br CN + What would be the rate law of this reaction? (Do you remember rate laws?) Why is this referred to as the S N 2 reaction? Reading : Section 9.4 Chemistry S-20ab Week 2 107
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E2 vs. S N 2: The “GFP” Reaction Hierarchy To help decide which reaction will predominate, apply the “GFP” (good-fair-poor) reaction hierarchy. If all else is equal , choose the reaction that is at the top of the list: 1. S N 2 reactions: Require good steric interactions Good if the halide is methyl or 1° Fair if the halide is 2° Poor if the halide is 3° or if the nucleophile is very bulky (e.g.
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This note was uploaded on 07/28/2011 for the course CHEM S20 taught by Professor Evan during the Spring '11 term at Belhaven.

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s20 2011 week 2 day 4 - post - R and S Nomenclature...

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