
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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The given question was incorrectly answered, please identify what the errors made were. Then correctly answer and explain the given the question.

Transcribed Image Text:Question 2
Compound A, CSH10, is reacted with Br2 in H20. The product is then reacted with acetylide anion, C2H,
followed by Lindlar's catalyst. The resulting alkene is reacted with BH3 followed by NaOH and hydrogen
peroxide and finally Jones reagent to give final Compound B, C,H14O3. Using the provided spectral data, draw
the structure of B and label all provided spectral data. You may show the intermediate products for partial
credit.
NOTE: Ignore the side reaction that occurs in step 2. You don't know the reaction that would prevent it so I
didn't include it.
1. Br2/H20
2.
C7H14O3
3. Lindlar's cat.
4. BH3
5.H2O2, NaOH
6. Jones reagent
CSH10
Compound A
Compound B
IR (cm-1):
2745 & 1679
13CNMR (ppm, splitting):
132, s; 119, d; 26, q; 17, q; 13, q
1HNMR (ppm):
5.19, 1H, q; 1.64, 6H, s; 1.56, 3H, d
IR (cm 1):
3200 (broad), 1712 (strong)
13CNMR (ppm, DEPT):
179/none; 77/none; 42/same; 35/invert;
27/same; 8/same
HNMR (ppm):
11.8, 1H, s (exchanges w/ D2O); 4.5, 1H, s
(exchanges with D20); 2.1, 2H, d; 1.7, 1H,
sextet; 1.2, 6H, s; 0.9, 3H, d

Transcribed Image Text:IR (cm-1):
3200 (broad)- OHstretch
1712 (strong)-CEogtretch
13CNMR (ppm, DEPT):
179/none e
77/nonea
42/same
35/invertC
27/same
a
to
8/sameca
1HNMR (ppm):
11.8, 1H, s (exchanges w/ D20)
4.5, 1H, s (exchanges with D20) q
p"
2.1, 2H, de
1.7, 1H, sextgt b
1.2, 6H, sC
0.9, 3H, dC
0:
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