Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 18.13, Problem 28P
Interpretation Introduction
Interpretation: The given following esters which cannot undergo claisen condensation has to be predicted.
Concept introduction: When two molecules of an ester undergo condensation is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.
A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.
The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
€
+
Suppose the molecule in the drawing area below were reacted with H₂ over a platinum catalyst. Edit the molecule to show what would happen to it. That is, turn
it into the product of the reaction.
Also, write the name of the product molecule under the drawing area.
Name: ☐
H
C=0
X
H-
OH
HO-
H
HO-
-H
CH₂OH
×
Draw the Haworth projection of the disaccharide made by joining D-glucose and D-mannose with a ẞ(1-4) glycosidic bond. If the disaccharide has more than
one anomer, you can draw any of them.
Click and drag to start drawing a
structure.
X
Epoxides can be opened in aqueous acid or aqueous base to produce diols (molecules with two OH groups). In this question, you'll explore the
mechanism of epoxide opening in aqueous acid.
2nd attempt
Be sure to show all four bonds at stereocenters using hash and wedge lines.
0
0
Draw curved arrows to show how the epoxide reacts with hydronium ion.
100 +1:
1st attempt
Feedback
Be sure to show all four bonds at stereocenters using hash and wedge lines.
See Periodic Table
See Hint
H
A
5
F
F
Hr
See Periodic Table See Hint
Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.1 - Prob. 3PCh. 18.1 - Prob. 4PCh. 18.1 - PROBLEM 5♦
List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8PCh. 18.4 - Prob. 9PCh. 18.4 - Prob. 10P
Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
Knowledge Booster
Similar questions
- 03 Question (1 point) For the reaction below, draw both of the major organic products. Be sure to consider stereochemistry. > 1. CH₂CH₂MgBr 2. H₂O 3rd attempt Draw all four bonds at chiral centers. Draw all stereoisomers formed. Draw the structures here. e 130 AN H See Periodic Table See Hint P C Brarrow_forwardYou may wish to address the following issues in your response if they are pertinent to the reaction(s) you propose to employ:1) Chemoselectivity (why this functional group and not another?) 2) Regioselectivity (why here and not there?) 3) Stereoselectivity (why this stereoisomer?) 4) Changes in oxidation state. Please make it in detail and draw it out too in what step what happens. Thank you for helping me!arrow_forward1) Chemoselectivity (why this functional group and not another?) 2) Regioselectivity (why here and not there?) 3) Stereoselectivity (why this stereoisomer?) 4) Changes in oxidation state. Everything in detail and draw out and write it.arrow_forward
- Calculating the pH at equivalence of a titration 3/5 Izabella A chemist titrates 120.0 mL of a 0.7191M dimethylamine ((CH3)2NH) solution with 0.5501 M HBr solution at 25 °C. Calculate the pH at equivalence. The pk of dimethylamine is 3.27. Round your answer to 2 decimal places. Note for advanced students: you may assume the total volume of the solution equals the initial volume plus the volume of HBr solution added. pH = ☐ ✓ 18 Ar Boarrow_forwardAlcohols can be synthesized using an acid-catalyzed hydration of an alkene. An alkene is combined with aqueous acid (e.. sulfuric acid in water). The reaction mechanism typically involves a carbocation intermediate. > 3rd attempt 3343 10 8 Draw arrows to show the reaction between the alkene and hydronium ion. that 2nd attempt Feedback 1st attempt تعمال Ju See Periodic Table See Hint F D Ju See Periodic Table See Hintarrow_forwardDraw the simplified curved arrow mechanism for the reaction of acetone and CHgLi to give the major product. 4th attempt Π Draw the simplified curved arrow mechanism T 3rd attempt Feedback Ju See Periodic Table See Hint H -H H -I H F See Periodic Table See Hintarrow_forward
- Select the correct reagent to accomplish the first step of this reaction. Then draw a mechanism on the Grignard reagent using curved arrow notation to show how it is converted to the final product. 4th attempt Part 1 (0.5 point) Select the correct reagent to accomplish the first step of this reaction. Choose one: OA Mg in ethanol (EtOH) OB. 2 Li in THF O C. Li in THF D. Mg in THF O E Mg in H2O Part 2 (0.5 point) Br Part 1 Bri Mg CH B CH, 1 Draw intermediate here, but no arrows. © TE See Periodic Table See Hint See Hint ין Harrow_forwardSelect the product for the following reaction. HO HO PCC OH ○ OH O HO ○ HO HO HOarrow_forward5:45 Х Select the final product for the following reaction sequence. O O 1. Mg. ether 2.D.Oarrow_forward
- Based on the chart Two similarities between the molecule with alpha glycosidic linkages. Two similarities between the molecules with beta glycosidtic linkages. Two differences between the alpha and beta glycosidic linkages.arrow_forwardplease help fill in the tablearrow_forwardAnswer F pleasearrow_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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning