Base-promoted hydrolysis of methyl mesitoate occurs through an attack on the alcohol carbon instead of the acyl

Question:

Base-promoted hydrolysis of methyl mesitoate occurs through an attack on the alcohol carbon instead of the acyl carbon:

(a) Can you suggest a reason that accounts for this unusual behavior?
(b) Suggest an experiment with labeled compounds that would confirm this mode of attack.

Fantastic news! We've Found the answer you've been seeking!

Step by Step Answer:

Related Book For book-img-for-question

Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

See More Books

Question Posted: Apr 19, 2016 09:18 AM

See More Questions

Write the mechanism of the last step in the Gabriel amine synthesis, the base-promoted hydrolysis of a phthalimide to yield an amine plus phthalate ion.
Propose a mechanism for the base-promoted hydrolysis of g-butyrolactone:
The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of the ester group. Propose a mechanism for the reaction. - 213 H20 N 0 CH CH 0 N o CH3
In Exercises 7192, find and simplify the difference quotient f(x +h)-f(x) h -, h = 0
Missoula Railroad decided to use the high-low method and operating data from the past six months to estimate the fixed and variable components of transportation costs. The activity base used by...
4. An electronic plants production function is Q=5LK, where Q is its output, L is the amount of labor, and K is the amount of capital. The price of labor is $1 per unit of labor, and the price of...
Table B. 25 contains the golf data on strokes gained. Use all possible regressions to build a model for these data. Perform a residual analysis on the final model and comment on model adequacy. SG:...
Recall exercise 3 from Chapter 4 in which a country imposes an import fee on the crude oil it imports. Imagine that all the crude oil imports to the country are made by ships owned by its nationals....
Write a job advertisement for an External Auditor. Be sure to include the necessary skills and qualifications, duties and responsibilities for the auditor.
Consider a particle is confined in a three-level system. The probability of finding the particle in first level is 0.38, for second level 0.36, and for third level it is 0.26. What is the entropy of...
(a) Write stereochemical formulas for compounds A-F: 1. 2. 3. 4. (b) Which of the last two methods, 3 or 4, would you expect to give a higher yield of F? Why? cis-3-Methylcyclopentanol CoHSO2CIA...
What products would you obtain from acidic and basic hydrolysis of each of the following amides? (a) N, N-Diethylbenzamide (b) (c) NH2 HO (a dipeptide) CeHs
Using the chart of accounts numbering system, develop a chart of accounts that assigns an account number to each of the following accounts: a. Buildings b. Interest Revenue c. Bob Norton, Withdrawals...
States can generate revenue either by becoming the sole producer of a good or service and retaining the monopoly profits as revenue or by taxing goods or services provided by private competitive...
Suppose that you live in a house with a market and taxable value of $100,000 in a community with a property tax rate of $30 per $1,000 of taxable value. (a) What is your property tax amount? (b) What...
Suppose that your local school district wants to implement a program to assess teacher quality and success and to use that assessment as part of the evaluation of teachers that may affect their...
If all states offer essentially the same economic development incentives, then no state gains an advantage. Yet this is exactly what seems to happen in many cases. Why might states continue to offer...
If localities offer incentives such as tax breaks or taxexempt financing to firms that provide new investment in the community, a common complaint is that this disadvantages existing firms that...
Identify those situations in which a delegation of duties is not permitted.
Select a mass spectrometric technique with the highest mass resolution for identifying an unknown compound being eluted from a liquid chromatography column
Vinylidene chloride, H2C = CCl2, does not polymerize in isotactic, syndiotactic, and atactic forms. Explain.
Polymers such as polypropylene contain a large number of chirality centers. Would you therefore expect samples of isotactic, syndiotactic, or atactic polypropylene to rotate plane-polarized light?...
Draw the structure of an alternating segment of butyl rubber, a copolymer of isoprene (2-methyl-1, 3-butadiene) and isobutylene (2-methylpropene) prepared using a cationic initiator.
16. Nickel Inc. bought $500,000 of 3-year, 9% bonds as an investment on December 31, 2015 for $545,000. Nickel uses straight-line amortization. On May 1, 2016, $100,000 of the bonds were redeemed at...
5. Recursive method; what is printed if we call mystery (6, 12); public static void mystery (int x, int y) { if (x > y) { System.out.print ("/"); else if (x = y) { } else { System.out.print ("=" + y...
Simmonds Products has spent $158,500 (sunk cost) on research to develop low-fat imitation wine. The firm is planning to spend $210,000 on a machine to produce new wine. Shipping cost of $60,000 and...

Base-promoted hydrolysis of methyl mesitoate occurs through an attack on the alcohol carbon instead of the acyl

Question:

0-CH3 + OH- OCHOH Methyl mesitoate

Step by Step Answer:

a Steric hindrance presented by the diortho methyl group...View the full answer

Organic Chemistry

Students also viewed these Organic Chemistry questions