HW03 - Propose structures for the unknown compounds A , B ,...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #03 Deadline : 3:00 p.m., Monday, 2/4/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Compound A , a hydrocarbon having molecular formula C 6 H 12 , has the IR and 1 H NMR spectra shown below (on the left). When A is treated with BH 3 followed by H 2 O 2 /NaOH/H 2 O, Compound B (C 6 H 14 O) is isolated. Treatment of B with K 2 Cr 2 O 7 /H 2 SO 4 /H 2 O yields Compound C (C 6 H 12 O 2 ). The IR and 1 H NMR spectra of C are also given below (on the right).
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Unformatted text preview: Propose structures for the unknown compounds A , B , and C . Write each answer in the appropriate box below. It is not necessary to provide an explanation. 1H (s) disappears upon D 2 O shake 1H (quintet) 1H (broad s) Spectra for Compound A : Spectra for Compound C : 2H (q) 3H (t) 4H (m) 6H (t) 4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500 1) BH 3 2) H 2 O 2 , NaOH, H 2 O K 2 Cr 2 O 7 , H 2 SO 4 , H 2 O A B C...
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This note was uploaded on 09/04/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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