Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Instructions: Complete the questions in the space provided. Show all your work 1. You are trying to determine the rate law expression for a reaction that you are completing at 25°C. You measure the initial reaction rate and the starting concentrations of the reactions for 4 trials. BrO³¯ (aq) + 5Br¯ (aq) + 6H* (aq) → 3Br₂ (l) + 3H2O (l) Initial rate Trial [BrO3] [H*] [Br] (mol/L) (mol/L) | (mol/L) (mol/L.s) 1 0.10 0.10 0.10 8.0 2 0.20 0.10 0.10 16 3 0.10 0.20 0.10 16 4 0.10 0.10 0.20 32 a. Based on the above data what is the rate law expression? b. Solve for the value of k (make sure to include proper units) 2. The proposed reaction mechanism is as follows: i. ii. BrО¸¯ (aq) + H+ (aq) → HBrO3 (aq) HBrO³ (aq) + H* (aq) → H₂BrO3* (aq) iii. H₂BrO³* (aq) + Br¯ (aq) → Br₂O₂ (aq) + H2O (l) [Fast] [Medium] [Slow] iv. Br₂O₂ (aq) + 4H*(aq) + 4Br‍(aq) → 3Br₂ (l) + H2O (l) [Fast] Evaluate the validity of this proposed reaction. Justify your answer.
е. Д CH3 D*, D20
C. NaOMe, Br Br

Chapter 22 Solutions

Organic Chemistry (9th Edition)

Ch. 22.2A - Prob. 22.2PCh. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8PCh. 22.4 - Prob. 22.9PCh. 22.5A - Prob. 22.10PCh. 22.5A - Prob. 22.11PCh. 22.5B - Prob. 22.12PCh. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...
Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
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