EXAM_2_2007 - 1 1. (6 Points, 2 points total each) Give the...

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Unformatted text preview: 1 1. (6 Points, 2 points total each) Give the correct IUPAC name for the following structures: Br a) Include R/S H3CC CC(CH3)3 b) c) F 2. (6 Points, 2 points total each) Give the correct structure for the following names: a) Isobutyl bromide b) Vinyl chloride c) (2S,3R,4R)2-bromo-4-chloro-3-iodoheptane Fischer Projection 2 3. (7 Points) Draw all possible elimination products for the following E1reaction and place a circle around the most stable one. Br CH3 CH3 Dilute NaOH 4. (5 Points, total) How many possible monobromintion products are there for Compound A in the following reaction? (2 Points) Draw the structure of the major monobromintion product for Compound A. (3 Points) H3C Br2, hn H3C Compound A 3 5. (6 Points, 3 points total each box) Complete the following nucleophilic substitution reaction of first order. Br CH3CH2SNa SN1 Compound B + Inversion Product RetentionProduct 6. (4 Points) Draw all possible stereoisomers of 1,3-dichloro-1-methylcyclohexane. 7. (4 points total, 2 Points each box) Are there any threo and/or erythro enantiomer pairs in question 6? If yes, draw the structures of the enantiomers in the appropriate boxes below. Erythro Threo 4 8. (4 Points, 1 points Each) Label each of the compounds below as optically active (OA) or optically inactive (OI). OH H HO CH3 CH3 H Br OH H3C HO H OH H CH3 Br Br Br Br B A C D 9. (8 Points, 2 points Each) Assign the relationship of each of the following pairs as: Enantiomers (E), Diatereomers (D), Identical (I), or Constitutional isomers (C). H H3C Br H CH3 Cl H H3C Br Cl Br CH3 H A) Br B) CH3 Cl CH3 Cl C) Br CH3 Br H Br H CH3 CH3 H3C H Br Br Br D) H 5 10. (20 Points each, 5 points each) Outline an efficient synthesis for each of the following compounds starting with the given starting material and any necessary reagents. ? a) HC CH CN ? b) 6 O c) ? OH ? OCH2CH3 d) 7 11. (30 Points, 3 points Each box) Fill in the boxes with the appropriate reactants, reagents, or products. For the products, only draw the major organic product(s). Note: Make sure to show stereochemistry where appropriate. Br a) CH2CH3 (CH3)2CHONa E2 reaction 1) NaNH2 b) H3CH2CC CH 2) CH3CH2Br c) H3CH2CC CH 2 HCl OTOS d) CH3CH2CH2SNa Bimolecular reaction Show stereochemistry 8 e) 1) NBS, Peroxide, hn 2) NaNH2 (E2) OH 1) SOCl2 f) 2) CH3C CNa SN2 Show Stereochemistry g) Mg H2C CHCH2Br ether h) Br ONa Intramolecular SN2 9 CH2Ph i) 1) Tos-Cl 2) CH3SNa SN2 HO CH3 H Show Stereochemistry j) Br ...
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