Ochem Chapter 7 Alcohols And Ethers

Front 1

OH-

Back 1

hydroxyl

Front 2

alcohols can end with -ol or
"alcohol"

Back 2

know

Front 3

phenols =

Back 3

alcohols attached to aromatic rings

Ring-OH

Front 4

physical properties of alcohols

Back 4

high BP > hydrocarbons
hydrogen bonding
-increase the number of alcohols on a molecule = significant increase in BP

Front 5

hydrogen bonding occurs between H and...

Back 5

N, O, F

Front 6

hydroxyl atom of OH is weakly acidic/basic

Back 6

acidic

Front 7

hydroxyl hydrogens of phenols are >/</= hydroxyl hydrogens of alcohols?

Back 7

>

more acidic than hydroxyl hydrogens of alcohols

Front 8

phenol is slighty soluble in H2O

Back 8

know

Front 9

phenols are more/less acidic than aliphatic(non-aromatic) alcohols and can form salts with inorganic bases(NaOH)

Back 9

more

Front 10

with aliphatic alcohols, the more alkyl groups, the more/less acidic the molecule is

Back 10

less

Front 11

alkyl groups donate electron density and stabilize a + charge and destabilize a negative charge

Back 11

know

Front 12

more alkyl groups = decreased acidity

Back 12

know

Front 13

nucleophilic substitutions SN1/SN2

R-Br + OH- -->

Back 13

R-OH + Br-

Front 14

electrophilic addition

H2O + double bond

Back 14

adds H and OH- to d. bond

Front 15

nucleophilic addition

CH3-MgBr + R-(C=O)-H

Back 15

adds CH3 to carbon and makes Oxygen into alcohol

R-CH(OH)CH3

Front 16

oxidation
primary alcohols --> aldehydes --> carboxylic acids

2ndary alcohols --> ketones

Back 16

opposite direction = reduction

Front 17

synthesis of alcohols

Back 17

addition
substitution
reduction
phenol

Front 18

addition rxn
H2O + double bond

Back 18

alcohol

Front 19

substitution

CH3-Br + OH- -->

Back 19

CH3-OH + Br-

Front 20

reduction

aldehyde or carboxylic acid + LiAlH4 or NaBH4 and H+(acid) -->

Back 20

alcohol

Front 21

phenol synthesis

Ring-N2 +
H3O+ -->

Back 21

Ring-OH

Front 22

elimination rxns and alcohols

R-OH + H2SO4/Heat -->

Back 22

forms two products...the more stable one(more substituted double bond placement) will make up the majority of the product

Front 23

elimination and E2 = form primary or 2/3 substituted
E1 would generate...

Back 23

E2 = primary

E1 = 2ndary and tertiary substituted d. bond

Front 24

elimination reactions require an acidic solution

Back 24

know

Front 25

elimination reactions result in 2 products, the more stable one results in the majority

Back 25

know

Front 26

POCl3 can be used in elimination reactions with primary and secondary alcohols

Back 26

know

Front 27

substitution reactions

Back 27

hydroxide is AWFUL leaving group...must add a proton to the hydroxide to make it better leaving group

--> becomes SN1 reaction = h20 = leaving group

Front 28

subtitution rxn ex)

R-OH + HBr -->

Back 28

R-OH2+ + Br- -->

R-Br + H2O
`

Front 29

R-OH + SOCl2 -->

Back 29

R-Cl + SO2 + Cl-

Front 30

phenols undergo electrophilic aromatic substitution rxns since lone pairs on O donate e- density to the ring

Back 30

makes -Oh strongly activating
--ortho/para directing

Front 31

oxidation of alcohols

Cr or PCC

R-C-OH + PCC -->

Back 31

R-COH (double bonded O)

Front 32

PCC forms ketones from 2degree alcohols

PCC forms aldehydes from 1degree alcohols

Back 32

know

Front 33

Na2Cr2O7 oxidizes
1. 1degree alcohols to c. acids
2. 2degree alcohols to ketones

Back 33

know

Front 34

jones oxidation

CrO3 + H2SO4

R-OH -->

Back 34

C. acid

Front 35

ethers

Back 35

R-O-R
name larger chain, then smaller chain then "ether"
OR
smaller-oxy-larger

Front 36

ethers can form rings, so more angle strain = more reactivity

Back 36

know

Front 37

ethers are aprotic and unreactive

Back 37

know

Front 38

ethers do not undergo hydrogen bonding

Back 38

know

Front 39

ethers boil lower than alcohols because of absence of H-bonding

Back 39

know

Front 40

ethers are slightly polar and only slightly soluble in water

Back 40

know

Front 41

synthesis
R-O-Na + R-Br -->

Back 41

R-O-R + NaBr

Front 42

Ring-OH + R-Br + NaOH/H2O
--->

Back 42

Ring-O-R

Front 43

HO-(C2H2)-Br + Base/-H+ -->

Back 43

cyclic ether ring (2 carbons attached to oxygen)

Br is kicked off

Front 44

ringed ethers can be formed using RCOOOH structures that attack double bonds on the ring to form it...

Back 44

know pg 125

Front 45

ethers react with O2 to form peroxides

Back 45

know = ROOR

Front 46

ethers can be cleaved by addition of higher temperatures coupled with HBr or HI

Back 46

proceeds as SN1 or SN2
produce alkyl halides!!!