Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 21, Problem 21.52SP
An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57 °C. The IR spectrum of trimyristin shows a very strong absorption at 1733 cm−1. Basic hydrolysis of trimyristin gives 1 equivalent of glycerol and 3 equivalents of myristic acid (tetradecanoic acid).
- a. Draw the structure of trimyristin.
- b. Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Illustrate the Separation of cyclohexanamine and cyclohexanol by an extraction procedure ?
What reagents would you use to convert methyl propanoate to the following compounds? a. isopropyl propanoate b. sodium propanoate c. N-ethylpropanamide d. propanoic acid
1. Compare the acidity of alcohols, phenols, and carboxylic acid of comparable molecularweights.2. Compare the acidities of same concentrations of acetic acid, chloroacetic acid, cantrichloroacetic acid.3. Explain the structural effect influencing the acidity of phenol4. Compare the basicity of n-butylamine and diethylamine.
Chapter 21 Solutions
Organic Chemistry (9th Edition)
Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2PCh. 21.4A - Prob. 21.3PCh. 21.4A - Prob. 21.4PCh. 21.5C - Prob. 21.7PCh. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15PCh. 21.7B - Prob. 21.16PCh. 21.7C - Prob. 21.19P
Ch. 21.7C - Prob. 21.20PCh. 21.7C - Prob. 21.21PCh. 21.7D - Prob. 21.22PCh. 21.7D - The mechanism for acidic hydrolysis of a nitrile...Ch. 21.8A - Prob. 21.24PCh. 21.8C - Prob. 21.25PCh. 21.9 - Prob. 21.26PCh. 21.9 - Prob. 21.27PCh. 21.9 - Prob. 21.28PCh. 21.10 - Draw a mechanism for the acylation of anisole by...Ch. 21.10 - Prob. 21.30PCh. 21.11 - Prob. 21.31PCh. 21.11 - Prob. 21.32PCh. 21.12 - Problem 21-33 Propose a mechanism for the...Ch. 21.12 - Suggest the most appropriate reagent for each...Ch. 21.12 - Show how you would synthesize each compound,...Ch. 21.13 - Prob. 21.36PCh. 21.13 - Prob. 21.37PCh. 21.14 - Prob. 21.38PCh. 21.14 - Prob. 21.39PCh. 21.16 - Prob. 21.40PCh. 21.16 - Prob. 21.41PCh. 21 - Prob. 21.42SPCh. 21 - Give appropriate names for the following...Ch. 21 - Predict the major products formed when benzoyl...Ch. 21 - Predict the products of the following reactions....Ch. 21 - Prob. 21.46SPCh. 21 - Prob. 21.47SPCh. 21 - Prob. 21.48SPCh. 21 - Propose mechanisms for the following reactions.Ch. 21 - Prob. 21.51SPCh. 21 - An ether extraction of nutmeg gives large...Ch. 21 - Prob. 21.53SPCh. 21 - Show how you would accomplish the following...Ch. 21 - Prob. 21.55SPCh. 21 - Prob. 21.56SPCh. 21 - Prob. 21.57SPCh. 21 - Prob. 21.58SPCh. 21 - Prob. 21.59SPCh. 21 - Explain this curious result. What does this...Ch. 21 - Prob. 21.61SPCh. 21 - Prob. 21.62SPCh. 21 - Prob. 21.63SPCh. 21 - A chemist was called to an abandoned aspirin...Ch. 21 - Prob. 21.67SPCh. 21 - The IR spectrum, 13ONTVTR spectrum, and 1HNMR...Ch. 21 - Prob. 21.69SPCh. 21 - Prob. 21.70SPCh. 21 - Prob. 21.71SP
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
- a. Explain why N-methylethanamine has a higher boiling point than trimethylamine even though they have the same molecular weight b. Explain the observed trend in the melting points for four isomers of molecular formula C7H16arrow_forwardgive the reagents used in the following: 1. What was the reagents used in the chromic acid test of ethyl alcohol? 2. What was the reagents used in the chromic acid test of isopropyl alcohol? 3. What was the reagents used in testing for methanol of methanol? 4. What was the reagents used in sodium xanthate tes of ethyl alcohol? 5. What was the reagents used in sodium xanthate tes of isopropyl alcohol?arrow_forward5. Draw the structure of following compounds: a. methyl butanoate b. propyl ethanoate c. ethyl propanoate d. ethyl 3-methylhexanoate e. butyl hexanoate f. methyl 2-hexyl-3-oxocyclopentanecarboxylatearrow_forward
- What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid? a. ethyl butanoate c. methyl benzoate b. benzoic acid d. pentanoic acidarrow_forwardPropose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.arrow_forwardp-toluic acid is prepared from 3.42 grams of p-Bromotoluene. When p-Bromotoluene was mixed with dry ether, the mixture was warmed until the ether begins to boil (34.6 °C). When the reaction is almost complete, dry ice (3-4 mL in a beaker) was prepared and the mixture was poured into it. After some time, 5 mL of 6 N HCl was added. The solvent used for the recrystallization is 100 mL of 30% ethanol. The reaction equation is given on the figure. What is the actual yield? What is the theoretical yield? How many moles of p-toluic acid was produced?arrow_forward
- Acetal and Hemiacetal formation: c. Acetal/hemiacetal CH 3 ty CH H3C [ a. hemiacetal H3C d. Cyclic hemiacetal Gyertych OH Esterification/Amidation: e. Fisher esterification OH + CH₂OH + H3C CH3 H OH + CH3OH H [H*] H₂SO4 H™ a. hemiacetal b.acetal + H₂Oarrow_forwardDraw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.arrow_forwardExamine the compounds and then select all the following statements that are correct. موالي 1 2 له 3 4 A. Compound 1 can be distinguished from Compound 2 using the lodoform test. B. Compound 2 can be distinguished from Compound 3 using the Schiff test. C. Compound 3 can be distinguished from Compound 4 using the Tollens' test. D. Compound 2 can be distinguished from Compound 4 using the Tollens test. E. Compound 1 cannot be distinguished from Compound 3 using either the Tollens', the Schiff, or the lodoform test.arrow_forward
- The ionones are fragrant substances present in the scent of iris and are used in perfume. A mixture of α- and β-ionone can be prepared by treatment of pseudoionone with sulfuric acid.Write a stepwise mechanism for this reaction.arrow_forwardPhosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents? a. one equivalent of methanol b. excess methanol c. excess propylamine d. excess waterarrow_forward11. Write chemical equations for the reaction of propanamide with each reagent below. a) Dil. H2SO4/heat b) Dil. NaOH/heatarrow_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 LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY