Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 18.1, Problem 3P
Interpretation Introduction
Interpretation: Remove a proton from the alpha carbon of
Concept introduction: The electrons left behind when a proton is removed from the alpha carbon of an amide are not readily delocalized. This is because the nitrogen of the
Thus the lone pair on the alpha carbon and the lone pair on the nitrogen compete for the delocalization onto the same oxygen.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Please indicate which is the most acidic compound in each of the following pairs: thank you
p-Nitrophenol and m-nitrophenol
4-Methylbenzoic acid and 4-chlorobenzoic acid
Benzoic acid and 4-nitrobenzoic acid
Draw the structure for the following compounds
It organic
1: 2,2 diiodo-3-pentenoic acid
2: N,N-diethylpropanamide
3: 2-pentanone
4: phenoxy benzene
5: N,N-diethylpropanamide
Draw the major organic product for the acid hydrolysis of cyclohexanimine.
"NH
Hgo+
HO
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
- Explain why a base can remove a proton from the alpha-carbon of N,N-dimethylethanamide but not from the alpha-carbon of either N-methylethanamide or ethanamide.arrow_forwardWhy is methyl salicylate so easily absorbed through the skin?arrow_forwardWhich one of the following compounds has the lowest pka? O 2,3-dimethylheptanoic acid 3,3-dichlorohexanoic acid 4-bromo-3-iodohexanoic acid O 4-bromo-3-chloroheptanoic acid 4-bromo-2-fluorohexanoic acidarrow_forward
- Two reactions occur when sodium hydroxide is added to methyl salicylate. One is immediate and one only occurs with reflux over time. What type of reaction occurs immediately and with which functional group on methyl salicylate does it react? What type of reaction occurs with reflux over time and with which functional group on methyl salicylate does it react?arrow_forwardN-(2-hydroxyphenyl) acetamide N-(3-hydroxyphenyl) acetamide N-(4-hydroxyphenyl) acetamide what are the physical descriptionarrow_forwardExplain why m-nitroaniline is a stronger base than p-nitroaniline.arrow_forward
- What are the derivate reagents for the following compound: MDMA (N-methyl-N-trifluoroacetyl-3,4-methylenedioxyamphetamine)?arrow_forwardUse the priority system to draw the structure of the following molecule: 2-methoxy-3-methyl-5-oxoheptanoic acidarrow_forwardCardiolipins are found in heart muscles. Draw the products formed when a cardiolipin undergoes complete acid-catalyzed hydrolysis.arrow_forward
- What is the IUPAC name for the following compound? CH₂CH₂CH -N–CHỊCH,CHỊCH, CH₂CH₂CH₂CH₂CH₂CH, Propylheptylcyclobutylamine Dibutylheptylamine None of the answers are true ON-cyclobutyl-N-heptyl-1-butanamine O N-butyl-N-cyclobutyl-1-heptanaminearrow_forwardRank the compounds in order of electrophilicity. (X > Y means X is more electrophilic than Y). Acyl chlorides > Anhydrides > Amides > Aldehydes Amides > Acyl chlorides > Anhydrides > Aldehydes Aldehydes > Acyl chlorides > Anhydrides > Amides O Acyl chlorides > Anhydrides > Aldehydes > Amidesarrow_forward9,10-Dihydroxyoctadecanoic acidarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning