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Unformatted text preview: 1 1) (6 pts. 2pts. Each) Give the correct IUPAC or common name for the following structures: a) OCH2CH3 b) OH c) Include R/S 2) (6 pts. 2pts. Each) Give the correct structure for the following compounds: a) Methylene chloride b) (1R,3R)-3-Ethoxycyclopentanol c) Triphenylmethanol 2 3) (4 Points) Draw a circle around the most stable carbocation for each pair.
Cl HO Cl a)
HO b) H3C CHOCH3 H3C CHNO2 4. (4 Points, total) How many possible monobromintion products are there for Compound A in the following reaction? (2 Points) Draw the structure of the most stable monobromintion product for Compound A. (2 Points) Br2, hn Compound A 3 5) (8 Points) Provide a stepwise mechanism for the following reaction and carefully label the appropriate intermediate for both 1,2-product and 1,4-product.
HCl 1,2-Product + 1,4-Product Compound B 4 6) (6 Points) Draw an energy diagram for the reaction of Compound B with HCl in question 5 assuming an exothermic process. You must clearly label the energy of activation, transition states, heat of reaction, reactants, reaction intermediate, kinetic product (1,2-product), and the thermodynamic product (1,4-product). 5 7. (9 Points) Provide mechanisms to account for the formation of each of the elimination products in the following E1 reaction.
H3C CH3 H3C CH3 H3C CH3 Br H3C CH3 Dilute NaOH + A B + C 6 8) (3 Points each box, 6 points total) Complete the following Diels Alder reactions. + O H3C CH3 Diene Dienophile 9) (6 Points, 3 points Each box) Complete the following nucleophilic substitution reaction of first order. CH2Ph H3C H H Br CH2CH3 Dilute NaOH + SN1 Inversion Product Retention Product 7 10) (6 Points each, 18 points total) Outline an efficient synthesis for three of the following compounds starting with the given starting material and any necessary reagents. Clearly cross the one that you do not wish to be graded.
CH2CH2OH ? b)
C CCH3 8 ? c) OH d) ?
Ph 9 11. (27 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)
CH3 (CH3)2CHONa E1 reaction 1) NaNH2
H3CH2CC CH 2) CH3CH2Br 3) Na, NH3(liquid) HO CHCH3 1) Na 2) CH3CH2CH2Br c) Br d) CH3CH2CH2SNa
SN2 reaction Show stereochemistry 10 1) NBS, Peroxide, hn e) 2) Mg, ether OH 1) SOCl2 f) 2) CH3CH2SNa SN2 Show Stereochemistry OH NaH Intramolecular SN2 g)
Br 11 CH2Ph h) 1) Ts-Cl 2) CH3NH2 SN2 H OH CH3 O H3C S O Cl Show Stereochemistry = Ts-Cl para-toluenesulfonyl chloride Br (CH3CH2CH2)2CuLi i) ...
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- Fall '07