Loose Leaf for Organic Chemistry
10th Edition
ISBN: 9781259626548
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education (edition 10)
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 21, Problem 55P
The
tumors. A key step in the synthesis of sarkomycin is the reaction of lactone ester A with potassium tert-butoxide in tetrahydrofuran to give the bicyclic compound B. Write a mechanism for this reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
When phenylacetaldehyde (C6H5CH2CHO) is dissolved in D2O with added DCl, the hydrogen atoms a to the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.
The following compound undergoes Benzilic Acid Rearrangementto yield a hydroxyacid salt. Propose a mechanism for the reaction, write the major product, and provide an explanation as to the preference of migration of one R group over the other.
In the presence of a trace of acid, d@hydroxyvaleric acid forms a cyclic ester (lactone).HO¬CH2CH2CH2CH2¬COOHd@hydroxyvaleric acid(a) Give the structure of the lactone, called d@valerolactone.(b) Propose a mechanism for the formation of d@valerolactone.
Chapter 21 Solutions
Loose Leaf for Organic Chemistry
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
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
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forward
- Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forwardFollowing is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardBrevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan- 2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.arrow_forward
- Predict the products of reactions of ethers and epoxides, including the following:(a) Cleavage and autoxidation of ethers(b) Acid- and base-promoted opening of epoxides(c) Reactions of epoxides with organometallic reagents(d) Cleavage of silyl ethersarrow_forwardPropylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule. A. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H2SO4/H2O), showing the correct stereochemistry. B. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water (base-catalyzed hydrolysis), showing the correct stereochemistry. C. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with a rotation in the opposite direction from the product of the base catalyzed hydrolysis.arrow_forward1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents. 2. Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.arrow_forward
- Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardBrevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acidcatalyzed cyclization of 6,7-dihydroxy-nonan-2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2- one. You may also use three-carbon alcohols and any required organic or inorganic reagents.arrow_forwardPhenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthetic route for this compound starting from 4-nitrosalicylic acid. The synthesis involves multiple steps. Specify all the reagents and the reaction conditions it may require in each step.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License