![EBK ORGANIC CHEMISTRY](https://www.bartleby.com/isbn_cover_images/8220103151757/8220103151757_largeCoverImage.jpg)
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
expand_more
expand_more
format_list_bulleted
Question
Chapter 25, Problem 25.31AP
Interpretation Introduction
Interpretation:
The mechanism for the formation of a racemic mixture of tert-butyl phosphate by heating the tetrabutylammonium salt of isotopically chiral phenyl phosphate in the
Concept introduction:
The tetrabutylammonium salt of isotopically chiral phenyl phosphate on heating in the polar aprotic solvent acetonitrile containing excess of tert-butyl alcohol first forms planar metaphosphate ion which is gets trapped by the solvent acetonitrile from either side which racemizes the phosphate by nucleophilic attack of tert-butyl alcohol.
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
(a) Which is more reactive towards Electrophilic aromatic substitution (EAS)?
(b) Which of the following is a a meta-substituted compound?
(c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)?
(d) Which is an ortho-substituted compound?
(a) Which is the correct structure of the alkyl halide substrate?
(b) Which is the correct structure of the nucleophile?
From the given structures which is(a) an acid halide? (b) a secondary amide (c) an aldehyde incapable of self-aldol consensation?
Chapter 25 Solutions
EBK ORGANIC CHEMISTRY
Ch. 25 - Prob. 25.1PCh. 25 - Prob. 25.2PCh. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 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 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21APCh. 25 - Prob. 25.22APCh. 25 - Prob. 25.23APCh. 25 - Prob. 25.24APCh. 25 - Prob. 25.25APCh. 25 - Prob. 25.26APCh. 25 - Prob. 25.27APCh. 25 - Prob. 25.28APCh. 25 - Prob. 25.29APCh. 25 - Prob. 25.30APCh. 25 - Prob. 25.31APCh. 25 - Prob. 25.32APCh. 25 - Prob. 25.33APCh. 25 - Prob. 25.34APCh. 25 - Prob. 25.35APCh. 25 - Prob. 25.36APCh. 25 - Prob. 25.37APCh. 25 - Prob. 25.38APCh. 25 - Prob. 25.39APCh. 25 - Prob. 25.40AP
Knowledge Booster
Similar questions
- Consider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forwardThe saccharide shown here is present in some plant-derived foods. (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s). (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not? (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not? (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not? (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.arrow_forwardthe following reaction scheme leads to the formation of compound C. give the structure of the final product C and of the intermediate products A and B and justify, using the mechanism, the formation of the product A. Give the serereochemistry of the final product obtainedarrow_forward
- Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?arrow_forward(i) Explain with the aid of a reaction mechanism why the synthesis is highly diastereoselective. (ii) Draw the structures of the enantiomer, and one epimer of J, and give definitions of these terms.arrow_forward22:43 10. Provide the following: the resonance structure of the intermediate that can resonate into the other intermediate that is given the product that results from the given resonance structure Specify which product is the kinetic product and which is the thermodynamic product . OH 50% H₂SO4 H~arrow_forward
- Experimental control is most clearly facilitated by means of…arrow_forwardWill the oxirane formed in either sequence rotate the plane of polarized light? Explain.arrow_forward(a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forward
- (a) Isoleucine has been prepared by the following sequence of reactions. Give the structure of compounds A through D isolated as intermediates in this synthesis.(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide would you choose as the starting material for this synthesis?arrow_forwardgive explanation in detailarrow_forwardCompare isoquinoline and quinoline..Explain their basicity.Which of them will be more susceptible to nucleophilic attack and electrophilic attack ? Explain the reason?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9780618974122/9780618974122_smallCoverImage.gif)
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning