PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 22, Problem 22.30P
Glucosamine is a dietry supplement available in many over-the-counter treatments for osteoarthritis. Reaction of acetyl
glucosamine
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Digitalis is a preparation made from the dried seeds and leaves of the purple foxglove,
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talis is used in medicine to increase the force of myocardial contraction and as a conduction
depressant to decrease heart rate (the heart pumps more forcefully but less often).
HC
OH
H,C
H
CH3
H.
H.
(a) Describe this glycosidic bond
OCH, H
A (b) Draw an open-chain Fischer projection
of this monosaccharide
CH3
H.
(e) Describe this glycosidic bond
OCH, HA
H.
HO H)
H.
OH
НО
(d) Name this monosaccharide unit
H.
OH
Digitalin
1. Glucosamine is a dietary supplement available in many over-the-counter treatments for osteoarthritis. Reaction ofacetyl CoA with glucosamine forms NAG, N-acetylglucosamine, the monomer used to form chitin, the carbohydratethat forms the rigid shells of lobsters and crabs. Given the following reaction, draw the structure of NAG.
Piracetam undergoes hydrolysis due to the presence in the structure:
A) lactone ring
B) lactam ring
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D) ester group.
Chapter 22 Solutions
PKG ORGANIC CHEMISTRY
Ch. 22 - Prob. 22.1PCh. 22 - Draw the three possible resonance structures for...Ch. 22 - Prob. 22.3PCh. 22 - Give an IUPAC or common name for each compound. a....Ch. 22 - Problem 22.5 Draw the structure corresponding to...Ch. 22 - Problem 22.6 Explain why the boiling point of is...Ch. 22 - Problem 22.7 How would the compounds in each pair...Ch. 22 - Problem 22.8 Deduce the structures of compounds ...Ch. 22 - Problem 22.9 Without reading ahead in Chapter 22,...Ch. 22 - Rank the compounds in each group in order of...
Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Problem 22.15 Draw the products of each...Ch. 22 - Problem 22.16 Draw the products of each reaction.
...Ch. 22 - Prob. 22.17PCh. 22 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.19PCh. 22 - Problem 22.20 Fenofibrate is a...Ch. 22 - Problem 22.21 What product is formed when the...Ch. 22 - How would you synthesize olestra from sucrose?
Ch. 22 - Problem 22.23 What is the composition of the soap...Ch. 22 - Problem 22.24 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.25PCh. 22 - Problem 22.26 Some penicillins cannot be...Ch. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Problem 22.30 Glucosamine is a dietry supplement...Ch. 22 - Draw the products of each reaction. a. c. b.Ch. 22 - Draw a tautomer of each compound.
a. b. c.
Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Prob. 22.35PCh. 22 - Problem 22.36 Outline two different ways that can...Ch. 22 - 22.37 Rank the following compounds in order of...Ch. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - 22.40 Give the IUPAC or common name for each...Ch. 22 - 22.41 Give the structure corresponding to each...Ch. 22 - Prob. 22.42PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - (a) Propose an explanation for the difference in...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - 22.47 Draw the organic products formed in each...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - 22.54 Draw a stepwise mechanism f or the following...Ch. 22 - 22.55 When acetic acid () is treated with a trace...Ch. 22 - Prob. 22.56PCh. 22 - Prob. 22.57PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - 22.64 What carboxylic acid and alcohol are needed...Ch. 22 - Problem 22.65 Devise a synthesis of each compound...Ch. 22 - Prob. 22.66PCh. 22 - Prob. 22.67PCh. 22 - Prob. 22.68PCh. 22 - Prob. 22.69PCh. 22 - 22.70 What polyester or poly amide can be prepared...Ch. 22 - 22.71 What two monomers are needed to prepare each...Ch. 22 - Prob. 22.72PCh. 22 - 22.73 How can IR spectroscopy be used to...Ch. 22 - 22.74 Rank the following compounds in order of...Ch. 22 - 22.75 Identify the structures of each compound...Ch. 22 - 22.76 Identify the structures of A and B, isomers...Ch. 22 - Prob. 22.77PCh. 22 - 22.78 Identify the structure of compound C...Ch. 22 - 22.79 Identify the structures of D and E, isomers...Ch. 22 - 22.80 With reference to amides A and B, the...Ch. 22 - Prob. 22.81PCh. 22 - Prob. 22.82PCh. 22 - Prob. 22.83PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
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- Digitalis is a preparation made from the dried seeds and leaves of the purple foxglove, Digitalis purpurea, a plant native to southern and central Europe and cultivated in the United States. The preparation is a mixture of several active components, including digitalin. Digitalis is used in medicine to increase the force of myocardial contraction and as a conduction depressant to decrease heart rate (the heart pumps more forcefully but less often).arrow_forwardFats belong to the class of organic compounds represented by the general formula, RCOOR', where R and R' represent hydrocarbon groups; therefore, fats are: a. ethers. b. soaps. c. esters. d. lipases.arrow_forwardDraw the structure of cyclopentanamine.arrow_forward
- Explain the meaning of the following: (a) Esterification (b) Saponification (c) Enantiomersarrow_forwardExplain amine catalysis in urethane bond formationarrow_forwardOxaloacetic acid (or 2‑ketosuccinic acid) is a very important intermediate in metabolism. The compound is involved in the citric acid cycle for energy production within the cell. However, the compound is unstable and slowly decomposes spontaneously. Draw the decomposition products.arrow_forward
- draw the structure of sodium fluoroacetate (Compound 1080, a controversial coyote poison)arrow_forwardd-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compounds by reacting with them in the liver to form glucuronides. Glucuronides are water soluble and, therefore, readily excreted. After ingestion of a poison such as turpentine or phenol, the glucuronides of these compounds are found in urine. Draw the structure of the glucuronide formed by the reaction of beta-d-glucuronic acid and phenol.arrow_forwardNAD is: B E) . Amines can be produced by: A) B) Oxidation of nitro compounds Reduction of nitro compounds Acidification of nitro compounds Hydrolysis of nitro compounds IUPAC name of the following compound is The reduced form of NADH A dehydrating coenzyme A hydrating coenzyme A methylating coenzyme The oxidized form of NADH A) 3-methylhexanoic acid 3-methylbenzoicacid 3-methylcyclohexanoic acid. 1-methylcyclohexanoic acid A) B) Peptide bonds are: A) B D) The compound 4-hydroxyhexanedioc acid has following functional groups (s) 2 Carboxylic acids alcohol and carboxylic acid ester and alcohol alcohol and aromatic group ක COOH Esters Amines Amides Carboxylic acids and amines CH₁ 3-metnyl кустоarrow_forward
- Kindly answer this questionarrow_forwardd-Glucuronic acid is found widely in plants and animals. One of its functions is to detoxify poisonous HO-containing compounds by reacting with them inthe liver to form glucuronides. Glucuronides are water soluble and, therefore, readily excreted. After ingestion of a poison such as turpentine or phenol, theglucuronides of these compounds are found in urine. Draw the structure of the glucuronide formed by the reaction of β-d-glucuronic acid and phenol.arrow_forwardDrinking methanol can cause blindness in humans, as well as a severe acidosis that may be life threatening. Methanol is toxic because it is converted in the liver to formaldehyde and formic acid by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase. Methanol poisoning is treated with dialysis and infusions of bicarbonate and ethanol. Explain why each treatment is used.arrow_forward
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