Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
Book Icon
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.

Expert Solution & Answer
Check Mark

Want to see the full answer?

Check out a sample textbook solution
Blurred answer
Previous
Chapter 22.7B, Problem 22.21P
Next
Chapter 22.8, Problem 22.24P
Students have asked these similar questions
5. Use the MS data to answer the questions on the next page. 14.0 1.4 15.0 8.1 100- MS-IW-5644 26.0 2.8 27.0 6.7 28.0 1.8 29.0 80 4.4 38.0 1.0 39.0 1.5 41.0 1.2 42.0 11.2 43.0 100.0 44.0 4.3 79.0 1.9 80.0 2.6 Relative Intensity 40 81.0 1.9 82.0 2.5 93.0 8.7 20- 95.0 8.2 121.0 2.0 123.0 2.0 136.0 11.8 0 138.0 11.5 20 40 8. 60 a. Br - 0 80 100 120 140 160 180 200 220 m/z Identify the m/z of the base peak and molecular ion. 2 b. Draw structures for each of the following fragments (include electrons and charges): 43.0, 93.0, 95.0, 136.0, and 138.0 m/z. C. Draw a reasonable a-fragmentation mechanism for the fragmentation of the molecular ion to fragment 43.0 m/z. Be sure to include all electrons and formal charges. 6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium ion (CsH6N) and show your work.
None
Stereochemistry: Three possible answers- diastereomers, enantiomers OH CH₂OH I -c=0 21108 1101 41745 HOR CH₂OH IL Но CH₂OH TIL a. Compounds I and III have this relationship with each other: enantiomers b. Compounds II and IV have this relationship with each other: c. Compounds I and II have this relationship with each other: d. *Draw one structure that is a stereoisomer of II, but neither a diastereomer nor an enantiomer. (more than one correct answer)

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
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
SEE MORE TEXTBOOKS