Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 23, Problem 23.75P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction is to be devised.
Concept introduction: The organic compound having conjugated diene and keto group are classified as dienone. The dienone undergoes rearrangement in presence of acid to form stable phenol derivative. This rearrangement is known as dienone-phenol rearrangement.
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Experiment 1
Data Table 1: Conservation of Mass - Initial Mass
Data Table 1
Data Table 2
Data Table 3
Data Table 4
Panel 1
Photo 1
Data Table 5
Reaction Mass of test tube and 5.0% HC₂H₂O2 (g)
#
(A)
(B)
Mass of NaHCO, (g) Mass of balloon and NaHCO, (g)
(C)
0.10
1
0829
14.38g
0.20
2
0.929
14.29g
0.35
1.00g
3
14.25g
0.50
1.14g
14.29
Experiment 1
Data Table 2: Moles of HC2H3O2
Reaction Volume of Mass of
Moles of HC₂H₂O₂
5.0%
Vinegar
(g)
(ML)
5.0
0.25
0042 mol
2
5.0
0.25
0042 mol
3
5.0
0.25
0042 mol
5.0
0.25
0042 mol
Experiment 1
Data Table 3: Moles of NaHCO3
Reaction Mass of NaHCO (g)
10g
20g
35g
50g
Experiment 1
Data Table 4: Theoretical Yield of CO₂
Reaction #
1
2
3
Experiment 1
Total mass before reaction (g)
(D=A+C)
15.29
15.21g
15.25g
15.349
Exercise 1
Data Table 1
Data Table 2
Data Table 3
Data Table 4
Panel 1
Photo 1
Data Table 5
Exercise 1-
Data Table 1
Data Table 2
DataTable 3
Data Table 4
Panel 1
Photo 1
Data Table 5
Exercise 1-
Moles of NaHCO
0012 mol
0025 mol
0044 mol
0062 mol…
The chemical reaction you investigated is a two-step reaction. What type of reaction occurs in each step? How did you determine your answer?
Chapter 23 Solutions
Organic Chemistry-Package(Custom)
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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