(Og) Chapter 7: Alcohols And Ethers

Front 1

Formula for alcohol

Back 1

-ROH

Front 2

Naming Alcohols

Back 2

As a general note, since the hydroxyl group is ranked very highly, when counting the carbon back bone you want to give it the lowest number you can

Front 3

Aromatic Alcohols

Back 3

One example is phenol in which you combine a benzene ring with an alcohol

Front 4

Why do alcohols have such high boiling points?

Back 4

Because they are capable of hydrogen bonding

Front 5

What are the three elements that are capable of hydrogen bonding?

Back 5

Flourine, Oxygen, and Nitrogen. This is because the strong electronegativity of each and the fact that each atom is capable of rendering a molecule very polar

Front 6

Physical Properties of phenol groups.

Back 6

The pheol group is very acidic. It has this property given its ability to give off protons easily.

Front 7

Electrons and Acidity

Back 7

--The more electrons donating group that are present, the less acidic a compound becomes. The reason being that as you donate more and more electrons, the anion becomes less and less stable and is less likely to give off its electrons.
--Something becomes more acidic when the molecule is capable of spreading out the negative charge and remaining stable despite the negative charge

Front 8

Caboxylic Acid + LiAlH4/H3O

Back 8

This reaction will create an alcohol by reducing and remove the double bonded oxygen and just alcohol

Front 9

Aldehyde + NaBH4/H30

Back 9

This will lead to the creation of an alcohol by reducing the double bonded oxygen and turning it into a hydroxy group

Front 10

How do you create a phenol?

Back 10

Take a benzene with an NH2 on one end and a Br on the other end. Treat it with HNO2/H2SO4. The HSO2 will undergo an ion exchange reaction with the HSO4 in which there will be a N2+HSO4- group and that end. Then treating the compound with acid will turn that group into an OH group

Front 11

Alcohols + H2SO4

Back 11

This will lead to an elimination reaction in which the alcohol will be removed and a double bond will be placed instead

Front 12

Three ways to turn an OH group into a good leaving group.

Back 12

Protonate, Tosylate, or form inorganic ester

Front 13

Alcohol + HBr

Back 13

The H+ will protonate the OH group making it a water. The water will leave the group and the negatively charged Br group will attack the positively charged carbocation

Front 14

Tosyl Chloride + Alcohol

Back 14

The tosyl chloride will attach to the alcohol. Then if you treat it with NaI, the I will displace the Tosyl group and create a haloalkane

Front 15

Thionly Chloride + Alcohol

Back 15

The thionly chloride will attack the alcohol and create a haloalkane. SOCL will attach to the O group of the alcohol creating an inorganic ester and then the negative Cl- group attack that ester and create a haloalkane

Front 16

PCC + Alcohol

Back 16

PCC will turn the hydroxy group of the alcohol into a carbonly group on the terminal end which is an aldehyde

Front 17

Na2Cr2O7 + Alcohol

Back 17

This will turn a hydroxy group into a carbonyl group

Front 18

CrO3, H2SO4/Acetone + Alcohol

Back 18

Will turn a primary alcohol in a carboxylic acid and secondary alcohol into a ketone.

Front 19

PBr3 + Alcohol

Back 19

This will create an alkyl bromide.

Front 20

Physical Properties of Ether

Back 20

Ethers are generally aprotic and as such lack the capability to hydrogen bond.

Front 21

Williamson ether synthesis

Back 21

In this reaction, the alkoxide anion will react with an alkyl bromide. Negative charge of the alkoxide will attack the alkyl group of the alkyl bromide. The Br will be displaced and the oxygen will attach to the alkyl group which creates the ether

Front 22

Phenol William Ether Synthesis

Back 22

The hydroxy group of the phenol will attack a haloalkane. The halogen will be displaced and the oxygen will attach to the alkyl group

Front 23

What occurs between an ether an oxygen?

Back 23

Ethers and oxygen will react to form peroxides

Front 24

Cleavage of Ether

Back 24

Ethers will be cleaved in the presence of HBr of HI

Front 25

Two types of epoxide opening

Back 25

Acid catalyzed and Base catalyzed

Front 26

Base catalyzed epoxide opening

Back 26

If an epoxide is exposed to a base, the less substituted carbon will be attacked which means the O will end up on the less sub carbon

Front 27

Acid catalyzed epoxide opening

Back 27

If an epoxide it exposed to an acid, the acid will attack the more substituted carbon which means that the O will end up on the more sub carbon