![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_largeCoverImage.gif)
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 22, Problem 22.62P
A newer generation of antipsychotics, among them clozapine, are now used to treat the symptoms of schizophrenia. These drugs are more effective than earlier drugs in improving patient response in the areas of social withdrawal, apathy, memory, comprehension, and judgment. They also produce fewer side effects such as seizures and tardive dyskinesia (involuntary body movements). In the following synthesis of clozapine, Step 1 is an Ullmann coupling, a type of nucleophilic
- (a) Show how you might bring about formation of the amide in Step 2.
- (b) Propose a reagent for Step 3.
- (c) Propose a mechanism for Step 4.
- (d) Is clozapine chiral? If so, how many of the possible stereoisomers are formed in this synthesis?
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Trending nowThis is a popular solution!
![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known
as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes
fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of
the neurotransmitter serotonin in the synapses of the central nervous system follow-
ing release of serotonin during excitation of individual nerve cells. Between firings, the
serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of
reuptake has the effect of increasing the time serotonin molecules remain in the syn-
apses following excitation, leading to a therapeutic effect. In one synthesis of parox-
etine, the following reagents are used. Draw the structures of synthetic intermediates A
and B.
F
НО
SOCI,
A
B
HO
Pyridine
Cromolyn sodium, developed in the 1960s, has been used to prevent allergic reactions primarily affecting the lungs, as, for example, exercise-induced emphysema. It is thought to block the release of histamine, which prevents the sequence of events leading to swelling, itching, and constriction of bronchial tubes. Cromolyn sodium is synthesized in the following series of steps. Treatment of one mole of epichlorohydrin with two moles of 2,6-dihydroxyacetophenone in the presence of base gives I. Treatment of I with two moles of diethyl oxalate in the presence of sodium ethoxide gives a diester II. Saponification of the diester with aqueous NaOH gives cromolyn sodium.
Q. Is cromolyn sodium chiral? If so, which of the possible stereoisomers are formed in this synthesis?
5 The compounds labeled benzophenone-3 (CH,O,) and benzophenone-5 (CHNAO,S) are found in certain sunscreens.
Would you expect a sunscreen made with benzophenone-3 or benzophenone-5 to be more waterproof? Explain your choice.
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 22.1PCh. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3PCh. 22.2 - Prob. 22.4PCh. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...
Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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
- Terpin, prepared commercially by the acid-catalyzed hydration of limonene, is used medicinally as an expectorant for coughs. (a) Propose a structural formula for terpin and a mechanism for its formation. (b) How many cis, trans isomers are possible for the structural formula you propose?arrow_forward2. a-pinene is one of the constituents of turpentine. It can be found in many essential oils, such as that of rosemary, eucalyptus oil, and orange peels. Another common place to find a-pinene is cannabis plants. The concentration in marijuana is believed to contribute significantly to the side effects felt (such as memory impairment). H+ Propose a facile synthesis route for one of the diastereomers HBr Br2 CCl4 Br2 H₂O NaOEt EtOH LOH O3, -78°C (CH3)2S H2SO4 Aarrow_forwardPropose a mechanism for Step 4.arrow_forward
- Nicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nico- tinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide. COH COET CNH, Nicotinic acid Ethyl nicotinate Nicotinamide (Niacin)arrow_forwardTaxol is a powerful anticancer agent that was first isolated from the bark of the Pacific yew tree (Taxus brevifolia) in 1967 The structure of Taxol, shown below wasn't elucidated until 1971. Taxol prevents tumor growth by inhibiting the division C cells, or mitosis, in some types of cancer cells; and in other types of cancer cells, it induces cell death. or apoptosis. Taxol is now commonly prescribed as a treatment for breast and ovarian cancers. What functional groups are NOT present in taxol? NH OH .0.... Taxol (paclitaxel) HO Select one: O a. Aldehyde and Alcohol O b. Amide and Aldehyde Oc. Ester and Alcohol O d. Ketone and Ether O e. Carboxylic Acid and Amine OHarrow_forwardPropranolol binds to beta-adrenergic receptors with a Kj of 8.9 x 10-9M. What concentration of propranolol would be required to achieve a 50% reduction in the binding of the receptor agonist isoproterenol if the agonist concentration is 10ONM and its dissociation constant for the receptor is 4.8 x 10-8 M?arrow_forward
- Why are azo compounds good building blocks for organic dyes because aromatic azo compounds have alternating C-C and C=C bonds azo coupling removes the N-N triple bond azo coupling generates new C=C bonds O Azo coupling makes a longer conjugation systemarrow_forwardPropose a mechanism for the conversion of E to F. The reagent used in this synthesis is ethyl chloroformate. The other product of this conversion is chloromethane, CH3Cl. Your mechanism should show how the CH3Cl is formed.arrow_forwardAcid-catalyzed dehydrarion of 3-hydroxy-3-phenylcyctohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the IR spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm', what is its structure ?arrow_forward
- A solution of acetone [(CH3)2C=O] in ethanol (CH3CH2OH) in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm−1, and the 1H NMR spectrum is given here. What is the structure of the product?arrow_forwardIdentify the reagents you would use to convert 1-bromopentane into pentanamide. 1-bromopentane → pentanamide The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A. excess NH3 D. H3O+, heat G. Na₂Cr₂O7, H₂SO4, H₂O B. NaCN E. SOCI2 H. 1) LIAIH4; 2) H3O+ C. Mg F. NaOH I. PCC or DMParrow_forwardCiprofloxacin is a member of the fluoroquinolone class of antibiotics.(a) Which of its rings are aromatic?(b) Which nitrogen atoms are basic?(c) Which protons would you expect to appear between d 6 and d 8 in the proton NMR spectrum?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 LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY