Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 25, Problem 25.16P
Interpretation Introduction
Interpretation: The structure of enalapril is to be determined.
Concept introduction: The conversion of
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One step in the synthesis of sitaglipitin (Problem 17.14, a drug used to treat type 2 diabetes) involves reaction of the mixed anhydride A with B to form C. Draw a stepwise mechanism for this reaction.
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22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone
is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an
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5
3
6
CH₂O
CI
acetoacetic
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synthesis
HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
Nabumetone
(a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at
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(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
etone is completed.
16.51 Propose a plausible mechanism for the following transformation:
Heat
Chapter 25 Solutions
Organic Chemistry
Ch. 25 - Prob. 25.1PCh. 25 - Draw the structure of a compound of molecular...Ch. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Arrange the compounds in order of increasing...Ch. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Problem 25.7
Draw the product of each...Ch. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Draw the products of each acidbase reaction....Ch. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Problem 25.22
Which nitrogen atom in each compound...Ch. 25 - Which N atom in each drug is more basic? a. b. c.Ch. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.28
Draw the major product formed in...Ch. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Problem 25.31
Devise a synthesis of each compound...Ch. 25 - Prob. 25.35PCh. 25 - Problem 25.33
What starting materials are needed...Ch. 25 - Problem 25.34
(a) What two components are needed...Ch. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Prob. 25.44PCh. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Decide which N atom in each molecule is most basic...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - How would you prepare 3-phenyl-1-propanamine...Ch. 25 - Prob. 25.55PCh. 25 - Prob. 25.56PCh. 25 - Prob. 25.57PCh. 25 - Prob. 25.58PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.61PCh. 25 - Prob. 25.62PCh. 25 - Prob. 25.63PCh. 25 - Prob. 25.64PCh. 25 - Prob. 25.65PCh. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.72PCh. 25 - Tertiary (3) aromatic amines react with NaNO2 and...Ch. 25 - Prob. 25.74PCh. 25 - Devise a synthesis of each compound from benzene....Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78PCh. 25 - Prob. 25.79PCh. 25 - Synthesize each compound from benzene. Use a...Ch. 25 - Prob. 25.81PCh. 25 - Devise a synthesis of each compound from benzene,...Ch. 25 - Prob. 25.83PCh. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.86PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.88PCh. 25 - Prob. 25.89PCh. 25 - Prob. 25.90P
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- Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide.arrow_forwardReaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.arrow_forward16.48 D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions. CHO D omoss rosiglitazone Harrow_forward
- Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxibarrow_forwardThe analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.arrow_forward18.65 Propose a plausible synthesis for the following trans- formation. CH3 CH3 CH3arrow_forward
- Devise a synthesis of anastrozole, a drug used to reduce the recurrence of breast cancer (Section 22.18), from the given compounds. You may use any other needed organic compounds or inorganic reagents. CN Br Br HN- NC. anastrozolearrow_forwardReaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal anti-inflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.arrow_forward18.4 Characteristic Reactions of Anhydrides, Esters, and Amides 4 What product forms when ethyl benzoate is treated with each of the following sets? (a) H₂O, NaOH, heat H(b) H₂O, HCl, heatarrow_forward
- Reaction of X and phenylacetic acid forms an intermediate Y, which undergoes an intramolecular reaction to yield rofecoxib. Rofecoxib is a nonsteroidal antiinflammatory agent once marketed under the trade name Vioxx, now withdrawn from the market because of increased risk of heart attacks from long-term use in some patients. Identify Y and draw a stepwise mechanism for its conversion to rofecoxib.arrow_forwardDraw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach, Blattella germanica.arrow_forward19.54 Predict the major product(s) from the treatment of acetone with the following: (d) [H], (CH3)2NH, (-H2O) (e) [H], NH2NH2, (-H2O) (f) [H], NH2OH, (-H2O) (g) NaBH4, MeOH (h) RCO3H (i) HCN, KCN (j) EtMgBr followed by H₂O (k) (C6H5)3P=CHCH2CH3 (1) LIAIH, followed by H2Oarrow_forward
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