Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305864504
Author: Brent L. Iverson, Sheila Iverson
Publisher: Cengage Learning
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Question
Chapter 16, Problem 16.61P
(a)
Interpretation Introduction
Interpretation:
The given structural formula is
The given compound has to be synthesized from the below given starting materials.
(b)
Interpretation Introduction
Interpretation:
The given structural formula is
The given compound has to be synthesized from the below given starting materials.
(c)
Interpretation Introduction
Interpretation:
The given structural formula is
The given compound has to be synthesized from the below given starting materials.
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-AG|F=2E|V
3. Before proceeding with this problem you may want to glance at p. 466 of your textbook
where various oxo-phosphorus derivatives and their oxidation states are summarized.
Shown below are Latimer diagrams for phosphorus at pH values at 0 and 14:
Acidic solution
-0.93
+0.38
-0.51 -0.06
H3PO4 →H4P206 H3PO3 H3PO2 → P→ PH3
-0.28
-0.50
→
-0.50
Basic solution
3-1.12
-1.57
-2.05 -0.89
PO HPO →→H2PO2 P PH3
-1.73
a) Under acidic conditions, H3PO4 can be reduced into H3PO3 directly (-0.28V), or via the
formation and reduction of H4P2O6 (-0.93/+0.38V). Calculate the values of AG's for both
processes; comment.
(3 points)
0.5 PH,
0.0
-0.5-
2 3 9 3
-1.5
-2.0
Pa
H,PO
H,PO
H,PO
-3
-1 0
2
4
Oxidation state, N
2
b) Frost diagram for phosphorus under acidic
conditions is shown. Identify possible
disproportionation and comproportionation processes;
write out chemical equations describing them. (2 points)
c) Elemental phosphorus tends to disproportionate under basic conditions. Use data in…
These two reactions appear to start with the same starting materials but result in different products. How do the chemicals know which product to form? Are both products formed, or is there some information missing that will direct them a particular way?
What would be the best choices for the missing reagents 1 and 3 in this synthesis?
1. PPh3
3
1
2
2. n-BuLi
• Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like.
• Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is.
• Note: if one of your reagents needs to contain a halogen, use bromine.
Explanation
Check
Click and drag to start drawing a structure.
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Chapter 16 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Prob. 16.4PCh. 16.6 - Prob. 16.5PCh. 16.7 - Prob. 16.6PCh. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Prob. 16.8PCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...
Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
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