Ochem - t>f\L CDI Y Your name Your 10 I Chemistry 1088...

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I t>f\L CDI Y Your name ....................................... Your 10 #.......................................... . Chemistry 1088 First Midterm August 4 , --~ \ ~+ M\ frc<c{Ui. ... UJ / 'f!-Q.Y score 1 (140) Problem . 2 (300) 3 (170) 4 (200) 5 (200) 6 (160) 7 (180) 8 (200) total (1550) oercentaae , \ ,
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Problem 1 (1 4 points) How many types of hydrogens does each of the following molecules have? Predict the spin-spin splitting pattern that you would expect for each type of hydrogen in the 1H- NMR spectrum. ! i ---Y0-< o Problem 2 (30 points) .In the following transformations, the product or the reagents are missing. Complete the reactions by writing the structures of the missing chemicals in the boxes, o OH Jones 6 o 1) NaBH 4 cr o
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HBr heat + two organic pro'ducts 2) NaBH 4 ¢ ° r0 ° H 1) A9 20, NH 3 ,H 20 .. BiU
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e OOH ------ ... I cx # eOOH Problem 3 (17 points) Compound X (CSHlO) reacts with H2S04, HgS04, H20 and gives a single compound Y (CSH120). Y reacts with LiA1H4 followed by hydrolysis and yields Z (CSH140). Compound Z is a racemic mixture. The 1H-NMR of X, shows only two signals: one is a triplet and the other a quartet. a) Propose a structure for X, Y, and Z. (12 points) b) Assign the NMR signals to the corresponding Hs in X. (5 points) f\10+ .se~11 -Hu' J krlM. ..- "V\. .- CizeMA. 10f'l3
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Problem 4 (20 points) a) A useful method for obtaining aldehydes labeled with 18 0 is the reaction with water containing 18 0, in the presence of an acid catalyst. Propose an arrow-pushing mechanism for this transformation. (1 2 points)
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Ochem - t>f\L CDI Y Your name Your 10 I Chemistry 1088...

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