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CH310M-POW-11-KEY - CH 310/318M_POW-11 Williams Fall 2010...

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Unformatted text preview: CH 310/318M_POW-11 Williams Fall 2010 Due Date: NOON Mon, 11/15/10 Name (print): Signature: Do Homework in PEN! Please write the first three letters of your last name in the boxes CH 310/318M_POW-11 Williams Fall 2010 Due Date: NOON Mon, 11/15/10 1. Compound V is optically inactive. When it is treated with potassium tert-butoxide in tert- butanol, hydrocarbon W is obtained. When W is submitted to hydrogenation conditions (hydrogen gas with a palladium catalyst) Hydrocarbon X is obtained. When W is treated with ozone, followed by triphenylphosphine, only two products are yielded, aldehyde Y and glyoxal. Propose structures for V — Y and also write in the reaction conditions over each arrow that yield each product. (3 pt) CH 310/318M_POW-11 Williams Fall 2010 Due Date: NOON Mon, 11/15/10 2. (15)-2-methylcyclohexanol slowly racemizes on standing in the presence of dilute sulfuric acid. Use the arrow pushing formalism to propose a mechanism to account for this, being sure to include all lone pairs and charges. Show the active acid species and how it is regenerated (this reaction is catalytic in acid). Also, show why it is possible for both enantiomers to form in the stereochemical determining step of this mechanism (draw both enantiomers of the intermediates for this step, but you only need to proceed with one enantiomer to complete the mechanism.) FYI, the squiggle line here is another way of representing racemization at that carbon. (3pt) 0H dilute H2804 H30 slow dime ”38M mms m Mao l E? .. CD ltofisfoeirlflwb’rll ,0 H935 {'3 acme. .# > DKUC’ _____.__.— , Pf—-—:_-__:—.__ ———-—--—,_#——-—-— "'1‘ __ If ., fl .t . “w“ m» w. l a /\\ T: 0H; (‘3) 7i; -- _ (3) (TD hr L Mg» H 6) , {M96441 ., “l ”L" Li c RED/l “3H OK l “b \ 1%:ij H30 .4, \ Vi A, (j c (.3 . ls) ”l“? 0&1“th ibéétw two/up bid” © alerN/lt ' 7' ‘ Ham RovLimkp 4. M ‘9 (M‘tktlc mamas 72° CH 310/318M_POW-11 Williams Fall 2010 Due Date: NOON Mon, 11/15/10 3. Fill in the box. Predict the products for the given reactions. If a box is also placed under a reaction arrow, fill in what type of reaction you expect it to be (5N2, 5N1, E1 or E2) based on the reaction conditions. (2pts) V N—Br (NBS) the other enantiomer o H O is also formed here, . 2 but you were able to m CCI4 SN l separate them. .. or ( N'QS \ CLQJr ?Vififi\dr CK 1“) NaNHm NH NaSCH , , 3 WP 3 gal Br C7,. one enantiomer H2, Pd 1) 03, 2) (Meizs Draw as most stable chair CH 310/318M_POW-11 Williams Fall 2010 Due Date: NOON Mon, 11/15/10 4. Fill in the box. Predict the products for the given reactions. If a box is also placed under a reaction arrow, fill in what type of reaction you expect it to be (5N2, 5N1, E1 or E2) based on the reaction conditions. (2pts) '— warm2 KCN omso Nal. I _*_ acetone [Ar OH l’ cu—s—cna [I 1) NaH ...
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