Organic Chemistry: Principles And Mechanisms (second Edition)
Organic Chemistry: Principles And Mechanisms (second Edition)
2nd Edition
ISBN: 9780393630749
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 18, Problem 18.87P
Interpretation Introduction

Interpretation:

The given reaction is believed to proceed through the intermediate shown. The complete and detailed mechanism that leads to the formation of the intermediate is to be drawn.

Concept introduction:

This reaction takes place under mildly acidic conditions, and this is evidenced by the presence of carboxylic acid groups. The aldehyde reacts with NH3 in acidic conditions to form the imine according to the mechanism in equation 18-19, which is in equilibrium with a small amount of its protonated form.

Organic Chemistry: Principles And Mechanisms (second Edition), Chapter 18, Problem 18.87P , additional homework tip  1

For the given reaction we have:

Organic Chemistry: Principles And Mechanisms (second Edition), Chapter 18, Problem 18.87P , additional homework tip  2

The carbon nucleophile will be the enol. The ammonia deprotonates α-hydrogen of β-carboxylic acid to produce the enol that is nucleophilic at C.

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Choose the Lewis structure for the compound below: H2CCHOCH2CH(CH3)2 HH H :d H H H C. Η H H HH H H H H. H H H HH H H H H H- H H H C-H H H HHHH
Each of the highlighted carbon atoms is connected to hydrogen atoms.
く Complete the reaction in the drawing area below by adding the major products to the right-hand side. If there won't be any products, because nothing will happen under these reaction conditions, check the box under the drawing area instead. Note: if the products contain one or more pairs of enantiomers, don't worry about drawing each enantiomer with dash and wedge bonds. Just draw one molecule to represent each pair of enantiomers, using line bonds at the chiral center. More... No reaction. Explanation Check O + G 1. Na O Me Click and drag to start drawing a structure. 2. H + 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility 000 Ar P

Chapter 18 Solutions

Organic Chemistry: Principles And Mechanisms (second Edition)

Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Prob. 18.16PCh. 18 - Prob. 18.17PCh. 18 - Prob. 18.18PCh. 18 - Prob. 18.19PCh. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Prob. 18.25PCh. 18 - Prob. 18.26PCh. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Prob. 18.30PCh. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Prob. 18.36PCh. 18 - Prob. 18.37PCh. 18 - Prob. 18.38PCh. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Prob. 18.41PCh. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Prob. 18.48PCh. 18 - Prob. 18.49PCh. 18 - Prob. 18.50PCh. 18 - Prob. 18.51PCh. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - Prob. 18.55PCh. 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 - Prob. 18.63PCh. 18 - Prob. 18.64PCh. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71PCh. 18 - Prob. 18.72PCh. 18 - Prob. 18.73PCh. 18 - Prob. 18.74PCh. 18 - Prob. 18.75PCh. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79PCh. 18 - Prob. 18.80PCh. 18 - Prob. 18.81PCh. 18 - Prob. 18.82PCh. 18 - Prob. 18.83PCh. 18 - Prob. 18.84PCh. 18 - Prob. 18.85PCh. 18 - Prob. 18.86PCh. 18 - Prob. 18.87PCh. 18 - Prob. 18.88PCh. 18 - Prob. 18.89PCh. 18 - Prob. 18.90PCh. 18 - Prob. 18.91PCh. 18 - Prob. 18.92PCh. 18 - Prob. 18.93PCh. 18 - Prob. 18.94PCh. 18 - Prob. 18.95PCh. 18 - Prob. 18.96PCh. 18 - Prob. 18.97PCh. 18 - Prob. 18.98PCh. 18 - Prob. 18.99PCh. 18 - Prob. 18.100PCh. 18 - Prob. 18.101PCh. 18 - Prob. 18.102PCh. 18 - Prob. 18.103PCh. 18 - Prob. 18.1YTCh. 18 - Prob. 18.2YTCh. 18 - Prob. 18.3YTCh. 18 - Prob. 18.4YTCh. 18 - Prob. 18.5YTCh. 18 - Prob. 18.6YTCh. 18 - Prob. 18.7YTCh. 18 - Prob. 18.8YTCh. 18 - Prob. 18.9YTCh. 18 - Prob. 18.10YTCh. 18 - Prob. 18.11YTCh. 18 - Prob. 18.12YTCh. 18 - Prob. 18.13YTCh. 18 - Prob. 18.14YTCh. 18 - Prob. 18.15YT
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