Leila Sample Questions Week 5

Leila Sample Questions Week 5 - Chemistry 35: Organic...

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Chemistry 35: Organic Monofunctional Compounds Prof. Huestis, Fall 2008 TA: Leila Yeh Beach Section 5: October 27, 2008 Practice Problems 1. Compound A (C 4 H 9 NO) is soluble in water at any pH. Compound A also proves positive for a DNP and Tollens test but proves negative for an iodoform test. At pH 4 – 5, Compound A reacts to form Compound B (C 4 H 7 N). Adding water hydrolyzes Compound B back to Compound A . When reacted with H 2 / Ni, Compound B becomes Compound C (C 4 H 9 N) which is soluble in water at any pH. What are the structures of A , B , and C ? 2. Compound P (C 7 H 14 ) reacts with excess KMnO 4 to give two products, Compounds Q and R . Both Compounds Q and R are generally soluble in water at any pH. Also, both Compounds Q and R will react with excess methanol in acid to give two different products; Compound Q gives Compound S (C 4 H 8 O 2 ) and Compound R gives Compound T (C 6 H 14 O 2 ). When Compound R reacts with iodine and base, Compound Q is made along with colored crystals. What are the structures of P , Q , R , S , and T ?
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This note was uploaded on 02/13/2009 for the course CHEM 35 taught by Professor Dubois,j during the Fall '07 term at Stanford.

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Leila Sample Questions Week 5 - Chemistry 35: Organic...

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