Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 17.8, Problem BQ
Interpretation Introduction
Interpretation: The correct sterochemical descriptor for the substitution pattern of the cyclopropane ring in permethrin and bifentrin has to be determined.
Concept introduction:
Cis compounds are the geometrical isomers with the organic groups on the same side of the double bond.
The double bond of
In a cis isomer, groups are attached on the same side of the double bond while in the Trans isomer the groups are attached on the opposite sides.
Simple representation of cis and Trans isomer is as follows,
Permethrin and bifenthrin are the synthetic pyretherenoids now in common use in household and agricultural products.
Their structures are given below,
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- Rank the following groups of compounds from most acidic (1) to least acidic (4). Place the number
corresponding to the compound's relative rank in the blank below the structure.
a.
NO₂
NO₂
CH2CH2CH2CH2OH
CH3 CH3CH2CHOH
CH3CH2CH2CH2OH
NO₂
CH3CHCH2CH2OH
b.
OH
OH
CH₂OH
CO₂H
HC
CN
CN
CN
Give the major organic product(s) of the following reactions or sequences of reactions. Show all
relevant stereochemistry
a.
H
MgBr
1. ether
2. H₂O*
4
COH
b.
1. LIAIH, ether
2. H₂O
Choose the best reagent(s) for carrying out the following conversions from the list provided below.
Place the letter of the best choice in the blank to the left of the conversion. Reagents may be used
more than once.
a. 1.
CH3MgBr, ether
2. H3O+
NaOH
b. 1.
PBr3
2.
C.
2.
1. (CH3)3SiCl, (CH3CH2)3N
CH3MgBr, ether
3. H₂O*+
2. H3O+
e. 1. p-TosCl, pyridine
f.
نها
g.
2. NaOH
CrO3, H₂SO4, H₂O
1.
NaBH4, ethanol
2. H30*
h. PCC, CH2Cl2
Ovoldo-6
a.
b.
OH
OH
H
OH
O
any organic
Determine the rate law for sodium thiosulfate from the following data:
[Na2S2O3] Time (s)
0.0318 230.
0.0636 57.5
Chapter 17 Solutions
Organic Chemistry
Ch. 17.2 - Prob. 17.1PCh. 17.4 - Which is the stronger acid in each pair?Ch. 17.4 - Prob. 17.3PCh. 17.7 - Prob. 17.4PCh. 17.8 - Prob. 17.5PCh. 17.8 - Prob. AQCh. 17.8 - Prob. BQCh. 17.8 - Prob. CQCh. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.9 - Prob. 17.6P
Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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