Explore BrainMass
Share

Organic Chemistry: Synthesizing

This content was STOLEN from BrainMass.com - View the original, and get the already-completed solution here!

I am looking for an explanation to this question so that i can use them to review for my test. I have a vague idea of what is going on, i think i am just overwhelmed and need someone to simplify. Thanks.

Synthesizing ethers via acid-catalyzed condensation reactions has limited usefulness. The conditions (sulfuric acid and heat) are also conducive to elimination products. Primary alcohols will undergo dehydration to ethers at lower temperatures than dehydration to alkenes. Secondary and tertiary alcohols will give predominantly alkene products at the same temperature primary alcohols condense to give ethers. Primary alcohol condensation to ethers is also only useful when the ether is symmetric. The following question is to demonstrate the mess you would get if you tried to synthesize an asymmetric ether via acid-catalyzed dehydration. What two alcohols would you use if your goal was to synthesize butyl pentyl ether via acid-catalyzed dehydration of two alcohols?

(a) What is the skeletal structure of the alcohol with the least number of carbons.

(b) What is the skeletal structure of the desired ether.

Two other ethers will also be produced.
(c) What is the skeletal structure of the undesired ether with the least number of carbons.

Two elimination products will also need to separated out of the product mixture.
(d) What is the skeletal structure of the undesired elimination product with the least number of carbons.

© BrainMass Inc. brainmass.com October 17, 2018, 12:41 am ad1c9bdddf
https://brainmass.com/chemistry/acid-and-base-organic-chemistry/organic-chemistry-synthesizing-305710

Solution Summary

This solution assists with the organic chemistry problems attached.

$2.19
Similar Posting

Organic Chemistry Exercises

Please help with the following Organic Chemistry exercises.

Please see the attachment for the full questions.

1. Write a structural formula for each of the following compounds:
a. isopropyl methyl ether
b. trans-2-pentene oxide
c. 3-ethoxyhexane
d. ethylene glycol dipropyl ether

2. Name each of the following compounds.

3. Ethers and alcohols can be isomeric. Write the structures, and give the names for all possible isomers with the molecular formula C4H10O.

4. Write equations for the reaction of each of the following with (1) Mg in ether followed by (2) addition of D2O to the resulting solution.
a. (CH3)2CH CH2Br
b. CH3CH2OCH2CBr(CH3)2

5. Write equations for the best method to prepare each of the following ethers:
a. CH3CH2CH2OCH2CH3
b. (CH3)2CHCH2OCH2CH(CH3)2

6. Write an equation for each of the following reactions. If no reaction occurs, say so.

7. Write equations to show how 1-pentanol can be synthesized from bromopropane and ethylene oxide, using a Grignard reagent.

View Full Posting Details