Chapter 5 - Alcohol

Question 1

How do you make a alcohol when the alcohol isn’t the highest priority ?

Answer 1

Hydroxy

Question 2

What is a aromatic group with a hydroxyl group attached to it called ?

Answer 2

Phenol

Question 3

What makes the hydroxyl hydrogen particularly acidic?

Answer 3

Resonance I’m the phenol ring

Question 4

What are the three relative positions that must be indicated when a benzene contains two substituents ?

Answer 4

Ortho - adjacent carbon
Meta- two groups separated by one carbon
Para - two groups on opposite ends of a ring

Question 5

How does increasing the hydroxyl groups in a compound affect the boiling and melting points ?

Answer 5

Boiling point and melting points increase significantly

Question 6

How does hydrogen bonding occur ?

Answer 6

Hydrogen atoms are highly attracted to very electronegative atoms such as F,O and N
The slightly positive charge or the hydrogen attracts one of the slightly negative atoms to form a hydrogen bond

Question 7

How does the presence of alkyl branches on aromatic alcohol affect the acidity of a molecule ?

Answer 7

Decrease acidity

Question 8

What oxidant is used to to oxidize primary alcohols into anhydrides ? Why does the reaction stop after this conversion ? If another oxidant was used , aldehydes are hydrated to form what which are further oxidized into what ?

Answer 8

PCC
PCC lacks the water necessary to hydrate the aldehyde
Germinal diols ( 1,1-diols ), carboxylic acid

Question 9

What can secondary alcohols be oxidized into and by what oxidant ?

Answer 9

Ketones , by PCC or any other oxidant

Question 10

Can tertiary alcohols be oxidized ? Why ?

Answer 10

It is rare because they are as oxidized as possible and don’t have any H attached to the carbon group to which the hydroxyl group is attached to so that H group can’t participate in hydrogen binding

Question 11

What are examples of oxidizing agents that are stronger than PCC ?

Answer 11

Chromium containing oxidizing agents such as sodium and potassium dichromate

Question 12

What is the strongest oxidizing agent ?

Answer 12

CrO3 -chromium trioxide

Question 13

What is Jones oxidation ?

Answer 13

Chromium trioxide is dissolved in acetone , and a primary alcohol is oxidized into a carboxylic acid , a secondary alcohol is oxidized to ketone

Question 14

Since hydroxyl groups of alcohol make poor leaving groups what two compounds have been generated to cope with this ? What are their structures like ? What other function do they serve ?

Answer 14

Mesylate and tosylate because the make the hydroxyl group a stronger leaving group

Mesylate: - SO3 CH3
Tosylate : - SO3C6H4CH3

Mesyl and tosyl act as protective groups when you don’t want alcohol to react

Question 15

How are aldehyde and ketals prevented from reacting ?

Answer 15

They are converted to acetal and ketal by reacting with alcohols which prevents them from reacting with strong reducing agents such as LiAlH4

Question 16

What is the process called when acetal and ketal are returned to their reactive carbonyl form using an aqueous acid ?

Answer 16

Deprotection

Question 17

How are quinone produced ?

Answer 17

Treat,end of phenol with oxidizing agent

Question 18

What is the structure of quinone ?

Answer 18

6 carbon ring with double bonds on C2 and C5 and carbonyl groups on C1 and C4

Question 19

How are hydroxyquinones formed ?

Answer 19

When quinones are further oxidized ; gain variable number of OH

Question 20

What chemical properties allow ubiquinone to carry out its biological functions ?

Answer 20

Oxidation and reduction capacity

Long alkyl chain which allows it to be lipid soluble and act as a electron carrier within the phospholipid bilayer

Question 21

Why do longer alkane chains with a hydorxyl group have a higher boiling point ?

Answer 21

Increase in van der waal forces

Question 22

How does ubiquinone form ubiquinol?

Answer 22

Reduction