Question: Ketones react with alcohols to yield products called acetals. Why does the allcis isomer of 4-tert-butyl-l, 3-cyclohexanediol react readily with acetone and an acid catalyst

Ketones react with alcohols to yield products called acetals. Why does the allcis isomer of 4-tert-butyl-l, 3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal while other stercoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal. Use molecular models for help.

H CICH3)3 CICH)3 H3C CH3 Acid catalyst H20 H3C- An acetal

Step by Step Solution

★★★★★

3.32 Rating (158 Votes )

There are 3 Steps involved in it

1 Expert Approved Answer

Step: 1 Unlock

Draw the four possible isomers of 4tertbutylcyclohexane13diol Make models of these isomers als... View full answer

Question Has Been Solved by an Expert!

Get step-by-step solutions from verified subject matter experts

Step: 2 Unlock

Step: 3 Unlock

Document Format (1 attachment)

22-C-O-O-C (161).docx

120 KBs Word File

Students Have Also Explored These Related Organic Chemistry Questions!

Draw the more stable chair conformation for each of the following compounds: CI Cl Cl

Draw the more stable chair conformation for each of the following compounds: (a) -d-Galactopyranose (b) -d-Glucopyranose (c) -d-Glucopyranose

Draw the more stable chair conformation of -daltropyranose and label all substituents as axial or equatorial.

Suppose a state was trying to decide whether to fund primary and secondary education with a property tax or an income tax. What implications might this choice have for land use in the state?

Three years ago you purchased a Heinz corporate bond that pays 3.125 percent annual interest. The face value of the bond is $1,000. What is the total dollar amount of interest that you received from...

Let f: R2 R be C2 on R2 and set u(r, Î¸) = f(r cos Î¸, r sin Î¸). If f satisfies the Laplace equation; that is, if prove for each r Î¸ that ax2 ay 1au...

The main plot of disaster movies (which depict the antecedents, occurrence, consequences and usually solution of a catastrophe) such as Jurassic Park, King Kong, Airport and The Towering Inferno...

Lockheed, one of the largest defense contractors in the United States, reported EBITDA of $1,290 million in a recent financial year, prior to interest expenses of $215 million and depreciation...

For the entire year, the company sells 440 units of inventory for $60 each. Required: 1. Using FIFO, calculate (a) ending inventory, (b) cost of goods sold, (c) sales revenue, and (d) gross profit....

X Ltd. has 10 lakhs equity shares outstanding at the beginning of the accounting year 2016. The appropriate P/E ratio for the industry in which D Ltd. is 8.35. The earnings per share is Rs. 15 in the...

Imagine a unit circle in which a point is rotated A radians counterclockwise about the origin from the positive x-axis. Copy this table and record the x-coordinate and y-coordinate for each angle....

CP8-10-submit in Canvas (round all answers to the nearest dollar) n PV$1 FV$1 PVA FVA 5 6% 0.747258 4.212364 1.338226 5.637093 60 0.50% 0.741372 1.348850 51.725561 69.770031 1. You want to buy a...

Assume a budget for City has been approved and the following information is available: . Estimated inflow from revenue $900,000. Estimated inflow from general long-term debt $100,000. Transfer from...

You notice several adult guests playing in the pool. Their play is getting slightly more aggressive and loud and several guests who were near them have moved away. How would you respond?

Kubin Companys relevant range of production is 18,000 to 22,000 units. When it produces and sells 20,000 units, its average costs per unit are as follows: Average Cost per Unit Direct materials $...

1. You are developing a multimedia product to be sold on CD-ROM. You wish to use the following media assets within this product. How would copyright and intellectual property laws affect your use of...

Which one of the following is most likely a reason to not use fiscal deficits as an expansionary tool? A. They may crowd out private investment. B. They may facilitate tax changes to reduce...

In 1995 Miguel purchased a home for $130,000. In 2000 he sold it for $170,000 and immediately purchased another one for $180,000, which he sold in 2007 for $235,000. How much taxable capital gain, if...

For each of the following substances describe the importance of dispersion (London) forces, dipoledipole interactions, and hydrogen bonding: (a) HCl; (b) Br 2 ; (c) ICl; (d) HF; (e) CH 4 .

Azulene has an appreciable dipole moment. Write resonance structures for azulene that explain this dipole moment and that help explain its aromaticity.

(a) The iSH group is sometimes called the mercapto group. 6-Mercaptopurine is used in the treatment of acute leukemia. Write its structure. (b) Allopurinol, a compound used to treat gout, is...

Explain how 13C NMR spectroscopy could be used to distinguish the ortho-, meta-, and para-dibromobenzene isomers one from another.

Four benzenoid compounds, all with the formula C7H7Br, gave the following IR peaks in the 680-860-cm-1 region: A, 740 cm-1 (strong) B, 800 cm-1 (very strong) C, 680 cm-1 (strong) and 760 cm-1 (very...

Write structural formulas for each of the following: (a) 3-Nitrobenzoic acid (b) p-Bromotoluene (c) o-Dibromobenzene (d) m-Dinitrobenzene (e) 3,5-Dinitrophenol (f) p-Nitrobenzoic acid (g)...

Please explain and write readable When sorting through the payroll documents that Mr. Castle gave you, you find the following unentered timesheets for Dan Miller and Gregg Schneider. Timesheet Dec 16...