Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 16, Problem 16.45P
Draw a stepwise mechanism for the following reaction.
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A small artisanal cheesemaker is testing the acidity of their milk
before it coagulates. During fermentation, bacteria produce lactic
acid (K₁ = 1.4 x 104), a weak acid that helps to curdle the milk and
develop flavor. The cheesemaker has measured that the developing
mixture contains lactic acid at an initial concentration of 0.025 M.
Your task is to calculate the pH of this mixture and determine whether
it meets the required acidity for proper cheese development. To
achieve the best flavor, texture and reduce/control microbial growth,
the pH range needs to be between pH 4.6 and 5.0.
Assumptions:
Lactic acid is a monoprotic acid
H
H
:0:0:
H-C-C
H
:0:
O-H
Figure 1: Lewis Structure for Lactic Acid
For simplicity, you can use the generic formula HA to represent the acid
You can assume lactic acid dissociation is in water as milk is mostly water.
Temperature is 25°C
1. Write the K, expression for the dissociation of lactic acid in the space provided. Do not forget to
include state symbols.…
Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product
structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s).
Be sure to account for all bond-breaking and bond-making steps.
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Select to Edit Arrows
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H
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Rotation
Select to Edit Arrows
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:0:
:0:
S:
3:48 PM Fri Apr 4
K
Problem 4 of 10
Submit
Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product
structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s).
Be sure to account for all bond-breaking and bond-making steps.
Mg.
:0:
Select to Add Arrows
:0:
:Br:
Mg
:0:
:0:
Select to Add Arrows
Mg.
Br:
:0:
0:0-
Br
-190
H
0:0
Select to Add Arrows
Select to Add Arrows
neutralizing workup
H
CH3
Chapter 16 Solutions
Organic Chemistry
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Draw a second resonance structure for each...Ch. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Determine the hybridization of the labeled atom in...Ch. 16 - Problem 16.10 Draw the structure consistent with...Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...
Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.17PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Rank the following dienophiles in order of...Ch. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.27PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Explain each statement using resonance theory. a....Ch. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Draw and name all dienes of molecular formula...Ch. 16 - Prob. 16.39PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.41PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.43PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.46PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.58PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Draw the products of each reaction. Indicate the...Ch. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Rank the following compounds in the order of...Ch. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74P
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