Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 19, Problem 19.36P
Interpretation Introduction
Interpretation:
The chemical equation for the formation of acetaminophen should be written.
Concept introduction:
Reaction of a phenol with an acetic anhydride in presence of acid catalyst gives an acetyl product. This reaction is known as acetylation.
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The analgesic acetaminophen is synthesized by treating 4-aminophenol with one equivalent of acetic anhydride. Draw a structural formula for acetaminophen.
Aspirin is the common name for the compound acetylsalicylic acid, widely used as a
fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the
willow family of plants, was derived from willow bark extracts. In folk medicine, willow
bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid
is administered in the form of aspirin which is less irritating to the stomach than salicylic
acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride.
A small amount of a strong acid is used as a catalyst which speeds up the reaction. In
this experiment, phosphoric acid will be used as the catalyst. The excess acetic acid
will be quenched with the addition of water. The aspirin product is not very soluble in
water so the aspirin product will precipitate when water is added. The synthesis
reaction of aspirin is shown below:
Actic anhydride
5 ml.
Acetic acid
Salicylic acid
28
Acetylsalicylie acid
Procedure
1)
Mix salicylic…
Why is methyl salicylate so easily absorbed through the skin?
Chapter 19 Solutions
Introduction to General, Organic and Biochemistry
Ch. 19.1 - Prob. 19.1PCh. 19.4 - Problem 19-2 Complete the equation for each...Ch. 19.4 - Prob. 19.3PCh. 19 - Prob. 19.4PCh. 19 - Write the IUPAC name for each compound.Ch. 19 - Prob. 19.6PCh. 19 - Prob. 19.7PCh. 19 - Prob. 19.8PCh. 19 - Prob. 19.9PCh. 19 - 0 Complete the equations for these reactions.
Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - 6 Why are Dacron and Mylar referred to as...Ch. 19 - 7 What type of structural feature do the...Ch. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - 0 Show how triphosphoric acid can form from three...Ch. 19 - 1 Write an equation for the hydrolysis of...Ch. 19 - 2 (Chemical Connections 19A) Locate the ester...Ch. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - 8 (Chemical Connections 19C) Once it has been...Ch. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - 4 (Chemical Connections 19F) Why do Lactomer...Ch. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - 8 In Chapter 22, we will discuss a class of...Ch. 19 - Prob. 19.39PCh. 19 - Prob. 19.40PCh. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49P
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- 18-31 Formic acid is one of the components responsible for the sting of biting ants and is injected under the skin by bee and wasp stings. The pain can be relieved by rubbing the area of the sting with a paste of baking soda (NaHCO3) and water, which neutralizes the acid. Write an equation for this reaction.arrow_forward17-35 Suppose that you take a bottle of benzaldehyde (a liquid, bp 179°C) from a shelf and find a white solid in the bottom of the bottle. The solid turns litmus red; that is, it is acidic. Yet aldehydes are neutral compounds. How can you explain these observations?arrow_forward18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forward
- 17-28 Show how acetaldehyde can form hydrogen bonds with water.arrow_forwardWrite an equation for the acid-base reaction between 2,4-pentanedione and sodium ethoxide and calculate its equilibrium constant, Keq. The pKa of 2,4-pentanedione is 9; that of ethanol is 15.9.arrow_forwardWith reference to the structures of acetylsalicylic acid (aspirin) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin tablets slowly decompose over time.arrow_forward
- A student is given a mixture of benzoic acid, 3-nitroaniline acid and naphthalene to separate. The student dissolves the mixture in an organic solvent and adds HCl to the solution. Two layers form. Which component(s) of the mixture remain in the organic solvent? Group of answer choices -naphthalene and benzoic acid -benzoic acid and 3-nitroaniline -naphthalene and 3-nitroaniline -naphthalenearrow_forwardWhen trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels,at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forwardComplete equations for the hydrolysis of the amides in Example 18.4 in concentrated aqueous NaOH. Show all products as they exist in aqueous NaOH and the number of moles of NaOH required for hydrolysis of each amide.arrow_forward
- Using molecular structures, what will happen in the following situations: 1) Benzoic acid is dissolved in diethyl ether and then 1 M HCl (aq) is added: 2) Ethyl 4-aminobenzoate is dissolved in dichloromethane and then 1 M NaOH (aq) is addedarrow_forwardCarboxylic acids are acidic enough to dissolve in both 10% NaOH and NaHCO3. Phenols, ArOH, are weak acids and most phenols will not dissolve in 10% NaHCO3. How would you separate a mixture of a carboxylic acid (RCOOH), an amine (RNH2), a phenol (ArOH) and a hydrocarbon (RH) using chemically active extraction? Draw a flow chart to illustrate your separation. Show each species in the aqueous and organic layers.arrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forward
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