Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18, Problem 13PP
PRACTICE PROBLEM 18.13
The antiepileptic drug valproic acid is 2-propylpentanoic acid (administered as the sodium salt). One commercial synthesis of valproic acid begins with ethyl cyanoacetate. The penultimate step of this synthesis involves a decarboxylation, and the last step involves hydrolysis of a nitrile. Outline this synthesis.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
• PRACTICE PROBLEM 18.14 Show how you could employ enamines in syntheses of the following compounds:
Een önös
(c)
(a)
(b)
(d)
OEt
Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4.
The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.
Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) aniline
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
Additional Science Textbook Solutions
Find more solutions based on key concepts
141. Design a device that uses as electrochemical cell to determine amount of
in a sample water Describe, in...
Chemistry: Structure and Properties (2nd Edition)
3.1 The reaction between reactant A (blue spheres) and reactant B (red spheres) is shown in the
following diag...
Chemistry: The Central Science (14th Edition)
The balance chemical reaction of given skeleton equation needs to be determined. Lithium(s) + Gold chloride (aq...
Chemistry: Matter and Change
If a compound has a molecular ion with an odd-numbered mass, then the compound contains an odd number of nitrog...
Organic Chemistry (8th Edition)
49. A 25.00-mL sample of an solution of unknown concentration is titrated with a 0.1322 M KOH solution. A volu...
Introductory Chemistry (5th Edition) (Standalone Book)
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
- Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, where as pyrrole is unreactive. What is the best explanation for this observed reactivity.arrow_forwardShow how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials.(a) anilinarrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forward
- Draw a complete arrow pushing mechanism for the specific Friedel Crafts acylation which involves the acylation of 1,3-benzodioxole using propionyl chloride as the acylating agent in the presence of zinc oxide nanoparticles as a catalyst. This reaction results in the formation of a propionylated product. The reaction is facilitated by the Lewis acid catalysis provided by zinc oxide nanoparticles.arrow_forwardProvide reagentsarrow_forwardPredict the major organic product of each of the following reactions.arrow_forward
- N-Methylbenzamide, an isomer of acetanilide, when allowed to react with HNO3/H2SO4 gives a different product from what is obtained from acetanilide. What is the structure of the mononitrated product? Why is it produced?arrow_forwardShow how Gabriel syntheses are used to prepare the following amines.(a) benzylaminearrow_forwardNifedipine (Procardia and Adalat) belongs to a class of drugs called calcium channel blockers and is effective in the treatment of various types of angina, including that in- duced by exercise. Show how nifedipine can be synthesized from 2-nitrobenzaldehyde, methyl acetoacetate, and ammonia. (Hint: Review the chemistry of your answers to Problems 19.43 and 19.54 and then combine that chemistry to solve this problem.) NO COOME MEOOC, acid + 2 `NO2 OMe +NH3 СНО H Nifedipinearrow_forward
- Provide reagentsarrow_forwardEach of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forwardAs a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?arrow_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
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY