Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 21, Problem 21.64P
Following 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?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Don't used Ai solution
Are lattice defects and crystal defects the same thing?
Don't used Ai solution
Chapter 21 Solutions
Organic Chemistry
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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
- A gas following mole compositions at 120 \deg F, 13.8 psia. N2% 2, CH 4% 79C2H6 % 19. Volume fractionn?arrow_forwardPlease correct answer and don't used hand raitingarrow_forwardOrder-disorder phenomenaa) do not have conductive properties.b) are cooperative.c) have few industrial implications.arrow_forward
- Unshared, or lone, electron pairs play an important role in determining the chemical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. CH. H₂ fo H2 H The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is HC HC HC CH The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c isarrow_forwardDraw curved arrows for the following reaction step. Arrow-pushing Instructions CH3 CH3 H H-O-H +/ H3C-C+ H3C-C-0: CH3 CH3 Harrow_forward1:14 PM Fri 20 Dec 67% Grade 7 CBE 03/12/2024 (OOW_7D 2024-25 Ms Sunita Harikesh) Activity Hi, Nimish. When you submit this form, the owner will see your name and email address. Teams Assignments * Required Camera Calendar Files ... More Skill: Advanced or complex data representation or interpretation. Vidya lit a candle and covered it with a glass. The candle burned for some time and then went off. She wanted to check whether the length of the candle would affect the time for which it burns. She performed the experiment again after changing something. Which of these would be the correct experimental setup for her to use? * (1 Point) She wanted to check whether the length of the candle would affect the time for which it burns. She performed the experiment again after changing something. Which of these would be the correct experimental setup for her to use? A Longer candle; No glass C B Longer candle; Longer glass D D B Longer candle; Same glass Same candle; Longer glassarrow_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 Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
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
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