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Organic Molecules and Reactions

I have 6 (sample) organic chemistry problems I need help with please (see attached as well). Short answer - please help.

1. Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order:
a. Cyclohexanol
b. 4-chlorophenol
c. 2-fluorocyclohexanol
d. 2-nitrophenol

2. Show the structure of all possible acid-catalyzed dehydration products of the following. If more than one alkene is possible, predict which ones will be formed in the largest amounts:
a. 1-ethylcyclohexanol
b. 3-methyl-1-3hexanol

3. Write an equation for each of these reactions:
a. 3-methyl-2-hexanol + CrO3-, H+ ?
b. 1-pentanol + aqueous NaoH ?
c. (CH3)2CHOH + Na?

4. Write equations for the best method to prepare each of the following ethers:
a. (CH3)2CHCH2OCH2CH2CH3
b. CH3CH2OCH2CH3

5. Give the structure of this product:
CH2=OCCH3 1. ? LialH4 2. ? H2O, H+

6. Complete the following equations:
a. CH3CH2=oCNHCH2CH3 ? LialH4
b. CH3CH2I+(CH3)2NH ?

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1. Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order:
a. Cyclohexanol
b. 4-chlorophenol
c. 2-fluorocyclohexanol
d. 2-nitrophenol
First, between cyclohexanol and phenol derivatives, in C6H5O- ion,one of the lone pairs on the oxygen atom overlaps with the delocalised electrons on the benzene ring. In other words, the lone pair becomes redistributed into the phenyl ring. This makes phenol derivatives more acidic than cyclohexanol derivatives.

For a and c, since in the 2-fluorocyclohexanol ion the halogen (F) can stabilize the conjugate anion via inductive delocalization, this makes c more acidic than a.

between b and d, since in the d ion the ...

Solution Summary

The solution discusses organic molecules an reactions.

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