Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18, Problem 12PP
PRACTICE PROBLEM 18.12
Outline all steps in a malonic ester synthesis of each of the following:
(a) pentanoic acid,
(b) 2-methylpentanoic acid, and
(c) 4-methylpentanoic acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenol
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.
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 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...Ch. 18 - Prob. 1QCh. 18 - Prob. 2QCh. 18 - Prob. 3QCh. 18 - Prob. 4QCh. 18 - Prob. 5Q
Additional Science Textbook Solutions
Find more solutions based on key concepts
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Use electronegativities to predict the direction of the dipole moments of the following bonds. a. CCl b. CO c. ...
Organic Chemistry (9th Edition)
Categorize the following reactions as synthesis, decomposition, or exchange reactions in the forward direction:...
General, Organic, and Biological Chemistry (3rd Edition)
For the reaction shown, calculate the theoretical yield of the product in grams for each of the initial quantit...
Introductory Chemistry (6th Edition)
77. Write a molecular equation for the precipitation reaction that occurs (if any) when each pair of aqueous so...
Chemistry: A Molecular Approach (4th Edition)
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
- Provide reagentsarrow_forward(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forward• PRACTICE PROBLEM 18.14 Show how you could employ enamines in syntheses of the following compounds: Een önös (c) (a) (b) (d) OEtarrow_forward
- Give clear handwritten solarrow_forwardSafrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, "Ecstasy") by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine. NHCH9 MDMA safrolearrow_forwardProvide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forward
- Provide a two step method to distinguish between the following compounds. (Propanal, butanal, butanone, propanone). Explain your choice of reagents and your expected results.arrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forwardShow how Gabriel syntheses are used to prepare the following amines.(a) benzylaminearrow_forward
- One of the following esters cannot undergo the Claisen condensation. Which one? Write structural formulas for the Claisen condensation products of the other two.arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardPropose a synthesis for each of the following compounds. (a) OH (b) (c)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
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY