Question: When 2-methyl-2, 5-pentanediol is treated with sulfuric acid, dehydration occurs and 2, 2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two

When 2-methyl-2, 5-pentanediol is treated with sulfuric acid, dehydration occurs and 2, 2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two oxygen atoms is most likely to be eliminated, andwhy?

CH 2,2-Dimethyltetrahydrofuran "C

Step by Step Solution

★★★★★

3.28 Rating (183 Votes )

There are 3 Steps involved in it

1 Expert Approved Answer

Step: 1 Unlock

HC CH CH3 CH3 HO H HOSO3H HCCH CH3 180 CH3 2 HO HO 2 HCCH H2O CH3 CH3 HCCH HC H 3 H... 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-E (71).docx

120 KBs Word File

Students Have Also Explored These Related Organic Chemistry Questions!

When ethylene glycol is treated with sulfuric acid, 1, 4-dioxane is obtained. Propose a mechanism for this transformation: H,SO, Ethylene glycol 1,4-Dioxane

Which sources of growth are most likely to be pro-trade? Which sources of growth are most likely to be antitrade? Which types of commodities are most likely to result in protrude consumption?...

Suggest a mechanism for thisreaction: CH,Br Br2 CH2=CHCH CH,CH,OH H,O

Background: In this experiment, you will synthesize a mixture of 2-methyl-1-butenes by acid catalyzed dehydration of 2-methyl-2-butanol (tert-Amyl alcohol). The product is separated by distillation...

In this experiment, you will synthesize a mixture of 2-methyl-1-butenes by acid catalyzed dehydration of 2-methyl-2-butanol (tert-Amyl alcohol). The product is separated by distillation from the...

Review Questions 1. Explain how a polymer and its monomers are similar 7. Your friend is going to try to follow a "no-fat" diet. to a freight train and its cars. 2. Identify each of the following...

Refer to Exercise 126. Iron(II) sulfate heptahydrate formed in the processing of ilmenite ore cannot be released into the environment. Its further treatment involves dehydration by heating to produce...

Regarding to the end point and equivalence point: End point is located very close to the equivalence point. All of above. End point: point where is the sudden change of physico- chemical property of...

In a chemical analysis experiment, an organic compound 'H' with the molecular formula C5H10O2 undergoes several diagnostic tests. Firstly, 'H' does not react with 2,4-Dinitrophenylhydrazine...

1. Jack Strong has $50,000 of wealth. He is participating in a Jujitsu competition. The prize is $10,000. He is guaranteed to win it (he had black belt) unless he breaks his arm. If his arm is...

[The following information applies to the questions displayed below.] Felix & Company reports the following information. Period Units Produced Total Costs 1 0 $ 4,680 2 3,988 3 4,380 4,980 *** 10 580...

Solve problem and graph. -10 8 -3u -6

What does an interperiod tax allocation account for? A . Temporary differences B . Permanent differences C . Error in prior tax years D . Change in service lives of depreciable assets

Saguenay Limited reports the following information: sales $1,110,000; sales returns and allowances $22,000; sales discounts $18,000; cost of goods sold $658,000; administrative expenses $160,000;...

Ramirez Inc., a publishing company, is preparing its December 31, 2017 financial statements and must determine the proper accounting treatment for the following situations. Ramirez has retained your...

The following is a manufacturing cost report of Marching Ants Inc. Evaluate and correct this report. Marching Ants Inc. Manufacturing Costs For the Quarter Ended June 30 Materials used in production...

Julie Company came into existence with a $2,000 cash investment by owners on January 1, 2011, and entered into the following transactions during 2011: Sales . . . . . . . . . . . . . . . . . . . . ....

Prepare the journal entries to record the following sales transactions in Fundy Corp.'s books. Fundy uses a perpetual inventory system. Jan. 2 Fundy sold $45,000 of goods to Xtra Inc., terms 2/10,...

Did the Federal Court in DCT v PM Developments Pty Ltd (2008) ATC 20-078; [2008] FCA 1886 rely on intrinsic materials to assist in the interpretation of the A New Tax System (Goods and Services Tax)...

Predict the bond angles of (a) F2C==CF2 (b) CH3Ci==CCH3 (c) HCi==N

Which of the following ions possess the electron configuration of a noble gas? (a) Na+ (b) Cl- (c) F+ (d) H- (e) Ca2+ (f) S2- (g) O2-

Write a Lewis structure for each of the following: (a) SOCl2 (b) POCl3 (c) PCl5 (d) HONO2 (HNO3)

Give the formal charge (if one exists) on each atom of the following: (a) (b) (c) (d) CH3-S CH3 CH-S-O:

Add any unshared electrons to give each element an octet in its valence shell in the formulas below and indicate any formal charges. All of the hydrogen atoms that are attached to heteroatoms have...

Dennis wants to determine if the discount rate really makes any difference in the net present value of a project. He feels that if a project is acceptable at one rate of return, it will be acceptable...