Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Textbook Question
Chapter 18.8, Problem DQ
The following sequence of steps is used to create the
- 1. Step 1 would best be performed at a pH below the pKa of ammonium.
- 2. Step 1 would create an imine that undergoes nucleophilic attack by cyanide in Step 2.
- 3. The hydrolysis of the nitrile created in Step 2 would be better performed in base rather than the acid shown.
- 4. Step 4 is a resolution of a racemic mixture that results from Steps 1–3 and does not require a chiral reagent.
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The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles.
Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following
electrophile followed by acid workup when relevant:
Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed.
Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector
tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the
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бль
EtO
OEt
Edit Drawing
The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is
formed when the conjugate base of diethyl malonate reacts with the following electrophile followed by acid workup when relevant:
Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed. Note: the eraser tool can
be used to erase bonds, and atoms can be moved by selecting them with the selector tool and then dragging the selected atom(s) to a
new position. If you make a mistake, you can use Ctrl-Z or the Undo tool.
OH
-CH₂
CH₂
Edit Drawing
Amidation Reactions
Part A
Learning Goal:
To identify characteristics common to all amidation reactions, and to apply these generalities in drawing specific amidation reactants
or products.
Part B
Amidation reactions are condensation reactions. In a condensation reaction, two molecules join with a new covalent bond, and this
results from the removal of a small molecule such as a water molecule. The reactants in amidation are a carboxylic acid and an
amine, and the products are an amide and a water molecule. The carboxylic acid reactant can be of any type. The amine can be
simple ammonia (NH₂). a primary amine. or a secondary amine. It cannot be a tertiary amine because tertiary amines lack the N-H
Aspartame, an amide, is the sweetener commonly used in diet cola.
COOH
CH2
<
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Review | Constants | Periodic Table
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Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 18.1PCh. 18.2 - Prob. 18.2PCh. 18.4 - Prob. 18.3PCh. 18.4 - Prob. 18.4PCh. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - Prob. AQCh. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - Prob. CQ
Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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