Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20.4, Problem 4P
Interpretation Introduction
Interpretation:
The major products obtained by the reactions of benzoyl chloride with the given compounds are to be determined.
Concept introduction:
The reaction of acyl chloride with
When acyl chloride reacts with alcohol and pyridine is used as a catalyst, it results in the formation of ester as the final product.
The reaction of acyl chloride with
The reaction of acyl chloride with water results in the formation of carboxylic acid as the final product.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
MeO
22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone
is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an
acetoacetic ester synthesis (Section 19.6).
5
3
6
CH₂O
CI
acetoacetic
ester
synthesis
HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
Nabumetone
(a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at
carbon 5 or 7.
(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
etone is completed.
provide the missing reagents as appropriate
Soved
Select the keyword or phrase that will best complete each sentence.
Key terms:
Compounds that contain a nitrogen atom bonded directly to a carbonyl carbon
are called
amides
amines
carboxyl groups
The conjugate bases of a carboxylic acid are
carboxylate anions
Compounds that conatin an OR group directly bonded to the carbonyl carbon
carboxylic acid
are known as
esters
is the base hydrolysis of an ester.
ethers
Fischer esterification
are salts of long-chain carboxylic acids.
Micelles
primary
Hydrolysis of a secondary amide wil produce a
amine.
and a
Saponification
Soaps
Primary
RCONH.
are compounds that have the general structure
secondary
Chapter 20 Solutions
Organic Chemistry - Standalone book
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.3 - Prob. 3PCh. 20.4 - Prob. 4PCh. 20.5 - Prob. 5PCh. 20.8 - Prob. 6PCh. 20.8 - Prob. 7PCh. 20.8 - Prob. 8PCh. 20.9 - Prob. 9PCh. 20.9 - Prob. 10P
Ch. 20.9 - Prob. 11PCh. 20.9 - Prob. 12PCh. 20.10 - Prob. 13PCh. 20.10 - Prob. 14PCh. 20.11 - Prob. 15PCh. 20.11 - Prob. 16PCh. 20.11 - Prob. 17PCh. 20.12 - Prob. 18PCh. 20.12 - Prob. 19PCh. 20.12 - Prob. 20PCh. 20.12 - Prob. 21PCh. 20.13 - Prob. 22PCh. 20.13 - Prob. 23PCh. 20.14 - Prob. 24PCh. 20.15 - Prob. 25PCh. 20.16 - Prob. 26PCh. 20.17 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Write a structural formula for the principal...Ch. 20 - Prob. 32PCh. 20 - Prob. 33PCh. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - The preparation of the sex pheromone of the...Ch. 20 - Prob. 44PCh. 20 - Suggest a reasonable explanation for each of the...Ch. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - A compound has a molecular formula of C8H14O4, and...Ch. 20 - Prob. 51PCh. 20 - Prob. 52DSPCh. 20 - Prob. 53DSPCh. 20 - Prob. 54DSPCh. 20 - Prob. 55DSPCh. 20 - Prob. 56DSPCh. 20 - Thioesters Thioesters have the general formula ....Ch. 20 - Prob. 58DSP
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
- PROBLEM 23.26 Draw the mechanism for the formation of phenol from bromobenzene and sodium hydroxide shown in the first reaction. Suppose, instead, that the deuterium-labeled bromobenzene shown in the second reaction were used. What percentage of the product would you expect to contain the deuterium atom? Explain. Br d 1. NaOH, A 2. H₂O, HCI OH 6 Br D 1. NaOH, A 2. H₂O, HCIarrow_forwardProblem 22 of 44 Draw the major product of this reaction. Ignore inorganic byproducts. Submit Assume that the water side product is continuously removed to drive the reaction toward products. PhNHNH2, TSOH Select to Drawarrow_forwardThioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?arrow_forward
- 17. Rank the acid derivatives with respect to their reactivity with water. acid halide > ester > acid anhydride > amide acid anhydride > amide > acid halide > ester amide > ester > acid anhydride > acid halide acid halide > acid anhydride > ester > amide A) B) C) D) 18. Disregarding A) 3 stereoisomers, how many different enols can the B-diketone CH3COCH₂COCH₂CH3 form? B) 1 C) 4 D) O E) 2arrow_forward3. Draw a stepwise mechanism for the following reaction. 1) NaH 2₂.8.30-50 2) H₂Oarrow_forwardCarbonyl compounds can be protonated on the carbonyl oxygen. Explain why propanoic acid is more readily protonated than propanone.arrow_forward
- How to prepare the following compound by the synthesis of malonic acidarrow_forwardpredict the organic product formed when BzCl (benzoyl chloride) reacts Dist a) aniline b) benzylamine c) dimethylamine d) isopropyl alcohol De waterarrow_forward1) 0.9 eq. LDA 2) MegSiCI 3) TICI, 4) H2SO4 H20 OH or OH QUESTION 9 what is the major product formed?arrow_forward
- 20. In the reaction of methylamine (CH,NH;) with benzoic anhydride, why is it recommended to use a sacrificial base? A) N-methylbenzamide reacts with methylamine B) N-methylbenzamide reacts with benzoic acid C) methylamine reacts with benzoic acid D) N-methylbenzamide reacts with benzoic anhydride E) Actually, a sacrificial base would not be needed for this reactionarrow_forwardWhich of the following reagents have no peroxy bond in their structure? a) Peroxyphosphoric acid b) Manganese dioxide c) Lead dioxide d) Perchloric acidarrow_forwardThe order of increasing acidity is Phenol < meta-cyanophenol < ortho-cyanophenol 1.how about para-cyanophenol??does it has higher acidicity than both ortho-cyanophenol and meta cyanophenol or lower?? 2.why does ortho-cyanophenol have higher acidicity than meta cyanophenol?? 3. why doesmeta cyanophenol have higher acidicity than Phenolarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you