Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Textbook Question
Chapter 19, Problem 19.61P
Following are the steps in one of the several published syntheses of frontalin, a pheromone of the western pine beetle.
- (a) Propose reagents for Steps 1–8.
- (b) Propose a mechanism for the cyclization of the ketodiol from Step 8 to frontalin.
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Obtain 2-methylbutanoic acid by malonic or acetylacetic synthesis (indicate the formulas of the compounds involved).
EFFICIENTS
SAMPLE READINGS
CONCENTRATIONS
Pigiadient)
TOMATO SAUCE (REGULAR)
TOMATO (REDUCED SALT)
TOMATO SAUCE (REGULAR)
TOMATO (REDUCED SALT)
58
6.274
3.898
301.7
151.2
14150
5.277
3.865
348.9
254.8
B
5.136
3.639
193.7
85.9
605
4.655
3.041
308.6
199.6
05
5.135
3.664
339.5
241.4
0139
4.676
3.662
160.6
87.6
90148
5.086
3.677
337.7
242.5
0092
6.348
3.775
464.7
186.4
PART3
5.081
3.908
223.5
155.8
5.558
3.861
370.5
257.1
4.922
3.66
326.6
242.9
4.752
3.641
327.5
253.3
50
5.018
3.815
336.1
256.0
84
4.959
3.605
317.9
216.6
38
4.96
3.652
203.8
108.7
$3
5.052
3.664
329.8
239.0
17
5.043
3.767
221.9
149.7
052
5.058
3.614
331.7
236.4
5.051
4.005
211.7
152.1
62
5.047
3.637
309.6
222.7
5.298
3.977
223.4
148.7
5.38
4.24
353.7
278.2
5
5.033
4.044
334.6
268.7
995
4.706
3.621
305.6
234.4
04
4.816
3.728
340.0
262.7
16
4.828
4.496
304.3
283.2
0.011
4.993
3.865
244.7
143.6
AVERAGE
STDEV
COUNT
95% CI Confidence Interval (mmol/L)
[Na+] (mg/100 mL)
95% Na+ Confidence Interval (mg/100 mL)
If we have two compounds: acetone (CH₃COCH₃) and acetic acid (CH₃COOH), applying heat to them produces an aldol condensation of the two compounds. If this is correct, draw the formula for the final product.
Chapter 19 Solutions
Organic Chemistry
Ch. 19.2 - Prob. 19.1PCh. 19.2 - Prob. 19.2PCh. 19.2 - Prob. 19.3PCh. 19.3 - Prob. 19.4PCh. 19.3 - Prob. 19.5PCh. 19.3 - Prob. 19.6PCh. 19.5 - Prob. 19.7PCh. 19.5 - Prob. 19.8PCh. 19.5 - Prob. 19.9PCh. 19.6 - Prob. 19.10P
Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
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