
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22.13, Problem 22.39P
Interpretation Introduction
Interpretation:
The mechanisms for the two given Dieckmann condensations are to be proposed.
Concept introduction:
An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(4 pts - 2 pts each part) A route that can be taken to prepare a
hydrophobic (water-repellent) aerogel is to start with
trichloromethylsilane, CH3SiCl3 as the silicon source.
a. What is the chemical reaction that this undergoes to form a
product with Si-OH groups? Write as complete of a chemical
equation as you can.
CI
CI-SI-CH3
CI
b. The formation of a byproduct is what drives this reaction - what is the byproduct (if you
didn't already answer it in part (a)) and how/why does it form?
b) Circle the substrate that would not efficiently generate a Grignard reagent upon reaction
with Mg in ether.
CI
Br
ד
c) Circle the Grignard reagents that contain incompatible functional groups.
MgBr
HO
MgBr
MgBr
MgBr
MgBr
HO
MgBr
Q2: Predict all organic product(s), including stereoisomers when applicable.
PCC
OH
a)
CH2Cl2
Page 2 of 5
Chem 0310 Organic Chemistry 1 HW Problem Sets
b)
.OH
Na2Cr2O7, H+
OH
PCC
CH2Cl2
c)
OH
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
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- d) Circle the substrates that will give an achiral product after a Grignard reaction with CH3MgBr. Harrow_forwardQ4: Predict the organic products for the following reactions. Then draw curved arrow electron- pushing mechanism for the reactions. a) NaBH4 EtOH Page 4 of 5 Chem 0310 Organic Chemistry 1 HW Problem Sets b) 요 1. Et₂O H MgBr 2. H+, H₂Oarrow_forward5Helparrow_forward
- (2 Pts) Draw correct Lewis structures for two different molecules that have C3H6 as theirchemical formulaarrow_forwardSynthesize the following:arrow_forwardDid you report your data to the correct number of significant figures? Temperature of cold water (°C) 4.0 Temperature of hot water ("C) 87.0 Volume of cold water (mL) 94.0 Volume of hot water (mL) 78.0 Final temperature after mixing ("C) 41.0 Mass of cold water (g) 94.0 Mass of hot water (g) 78.0 Calorimeter constant (J/°C) 12.44 How to calculate the calorimeter constantarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning

