Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6.3, Problem 5P
Would you expect the
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H₂C
ཏཱཏི 1 ནི
OH
1. Br2, PBг3
2. H₂O
H3C
OH
Br
The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can
be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the
acid bromide completes the reaction.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
:0:
H3C
Br
Br
+
:::OH2
Br
H₂O
H3C
Br
за
What would be the product if (S)-2-bromobutane underwent an S№1 reaction with
water in the presence of sodium carbonate (a weak base)?
(R)-2-butanol
(S)-2-butanol
A mixture of (R)- and (S)-2-butanol
Amantadine is effective in preventing infections caused by the influenza A virus and in
treating established illnesses. It is thought to block a late stage in the assembly of the
virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in
sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine.
CH,C=N
in H,SO,
Br
NHCCH3
NH2
1-Bromoadamantane
Amantadine
(a) Propose a mechanism for the transformation in Step 1.
(b) Describe experimental conditions to bring about Step 2.
Chapter 6 Solutions
Organic Chemistry - Standalone book
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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