Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 12, Problem 6PP
Interpretation Introduction
Interpretation:
The mechanism of the given reaction is to be provided.
Concept introduction:
Carbonyl groups of esters react with two equivalents of Grignard reagents and followed by hydrolysis to produce tertiary alcohols. The initial product formed between Grignard reagent and carbonyl ester is unstable. This complex structure loses magnesium, bromine, and alkoxide to form a ketone. The ketone is highly reactive with Grignard reagent, compared to esters. The ketone reacts immediately with the remaining Grignard reagent. This intermediate product is hydrolyzed to form tertiary alcohols.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Practice Problem 13.36b
Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the
following epoxide from acetylene:
H"
'Et
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) 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
B
C
D
DMP or PCC
На, Pt
EtBr
PHCH2BR
E
F
H
H2SO4, H20, HgSO4
МСРВА (RCO3зН)
Na, NH3 (/)
H2, Lindlar's cat.
I
K
TSCI, py
PhBr
NANH2
1) EtMgBr; 2) H30+
12.25 Propose an efficient
synthesis for asah of the
following transformations.
Br→
(b) Br
✓
효율적인 합성을 제안하라(여러 다
Don't provide handwritten solution.
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 1PPCh. 12 - Prob. 2PPCh. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 5PPCh. 12 - Prob. 6PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 8PPCh. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...
Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 12PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 14PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 20PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 22PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 24PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 27PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Predict the major organic product from each of the...Ch. 12 - 34. Synthesize the following compound using...Ch. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 39PCh. 12 - The problem below is directed toward devising a...
Knowledge Booster
Similar questions
- Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.(a) benzoic acid - phenyl cyclopentyl ketone (b) 1-bromohept-2-ene - oct-3-enalarrow_forward8.23 In each of the following indicate which reaction will occur faster. Explain your reasoning. (D) Solvolysis of 1-bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol (E) Solvolysis of isobutyl bromide or sec-butyl bromide in aqueous formic acid (F) Reaction of 1-chlorobutane with sodium acetate in acetic acid or with sodium methoxide in methanolarrow_forward16. Show how you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and any other necessary reagents. (a) cyclopentylphenylmethanol from benzaldehyde motor o (b) 아애 -OH fromarrow_forward
- 5.2. Provide the reagents needed to accomplish the following sequence of reactions. OH 1) Single stereoisomer 2)arrow_forwardStartting with benzene and using any other necessary reagents of your choice, design a synthesis for the following compound.arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forward
- When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forwardAcid-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_forwardProvide a stepwise synthesis for benzyl chloride to benzyl alcohol with reagents Na2CO3 and H2O.(including arrow-pushing mechanisms) Please show all the arrow pusharrow_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
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole