Chap 13: Alcohols, Phenols, Thiols, and Ethers

Question 1

What is the functional group of alcohols?

Answer 1

hydroxyl, -OH

Question 2

What is an alcohol?

Answer 2

carbon chain with an -OH attached

can by cyclic

Question 3

What is a phenol?

Answer 3

a hydroxyl group (-OH) attached to a benzene ring

Question 4

What is a thiol?

Answer 4

a carbon chain with an -SH attached

can be cyclic

Question 5

What is the IUPAC naming method for alcohols?

Answer 5

change -ane to -anol

e.g. methane into methanol

Question 6

How to name alcohol with 3+ carbons?

Answer 6

need to give the C# where -OH and any substituents are

Question 7

Naming alcohol with 2 or 3 hydroxyl group?

Answer 7

diol
triol
e.g. 1,2-butanediol

Question 8

Naming cyclic alcohols?

Answer 8

named cycloalkanol

if more than one substituent need to # the C

C1 is where the -OH is

Question 9

Naming phenols?

Answer 9

if a second substituent is present C1 is where the -OH is

after name as usual

Question 10

What is distinct about thiols?

Answer 10

have distinct odors

used to detect gas leaks

Question 11

Thiols are also known as what?

Answer 11

mercaptans

Question 12

Naming thiols?

Answer 12

add thiol to the alkane name of longest chain
methanethiol
2-propene-1-thiol

Question 13

What is an ether?

Answer 13

O attached by single bonds to two C atoms

O between two C’s

Question 14

Can an ether be between alkyls and aromatic rings?

Answer 14

yes

Question 15

Naming ethers?

Answer 15

smaller alkyl group = alkoxy
larger alkyl group = alkane
number C of the larger chain where the O is attached
1-ethoxybutane

Question 16

How are alcohols classified?

Answer 16

by number of alkyl groups attached to C bonded to the -OH

Question 17

What are the classifications of alcohols?

Answer 17

primary
secondary
tertiary

Question 18

What is a primary alcohol?

Answer 18

only has one alkyl group on -OH C

or has 2 H’s on -OH C

Question 19

What is a secondary alcohol?

Answer 19

has two alkyl groups on -OH C

or has one H on -OH C

Question 20

What is a tertiary alcohol?

Answer 20

has three alkyl groups attached to -OH C

of has no H on -OH C

Question 21

Which has higher MP/BP alcohols or ethers?

Answer 21

alcohols

Question 22

Why do alcohols have higher MP/BP than ethers?

Answer 22

the -OH forms a hydrogen bond which is harder to break

Question 23

Ethers have similar MP/BP to what?

Answer 23

alkanes

Question 24

Why do alkanes and ethers have similar MP/BP?

Answer 24

they are unable to form hydrogen bonds

Question 25

Are alcohols soluble in water?

Answer 25

sometimes

Question 26

When are alcohols soluble in water?

Answer 26

when it has 1-3 Carbons

Question 27

When are alcohols not soluble in water?

Answer 27

when it has 4+ Carbons

Question 28

What makes some alcohols soluble in water?

Answer 28

the polar -OH group

Question 29

Are ethers soluble in water?

Answer 29

sometimes, but only slightly

Question 30

When are ether able to be soluble in water?

Answer 30

when it has 1-3 Carbons, but it is only slightly soluble

Question 31

When are ethers never soluble in water?

Answer 31

when it has 5+ Carbons

Question 32

What makes some ethers slightly soluble in water?

Answer 32

they can form hydrogen bonds with water (but it is fewer hydrogen bonds than occurs between alcohols and water)

Question 33

Are phenols soluble in water?

Answer 33

only slightly

Question 34

What allows phenols to be slightly water soluble?

Answer 34

the -OH group can form hydrogen bonds with water

Question 35

Phenols can react with water to form what?

Answer 35

phenoxide ions (-OH ionizes slightly to make a weak acid)

Question 36

What happens in the dehydration of alcohols?

Answer 36

loose -H and -OH from adjacent carbon atoms forming a double bond

Question 37

What does the dehydration of an alcohol produce?

Answer 37

alkene and H2O

Question 38

What happens in the dehydration of a secondary alcohol?

Answer 38

a major and minor product are formed

Question 39

What is the rule for dehydration of secondary alcohols?

Answer 39

major product is removing H from C that has the smaller # of H atoms and forming the double bond b/w that C and and the C with the -OH minor product is removing the H from C that has the larger # of H atoms and forming a double bond b/w that C and the C with the -OH known as Saytzeff's rule

Question 40

What is oxidation?

Answer 40

increases the number of C-O bonds by adding -O or losing -H

Question 41

What is reduction?

Answer 41

reduce the number of bonds b/w C-O

Question 42

Which alcohols can be oxidized?

Answer 42

primar and secondary

Question 43

Why can't tertiary alcohols be oxidized?

Answer 43

because there is no -H to remove

Question 44

What is the product of oxidizing a primary alcohol?

Answer 44

aldehyde which further oxidizes into a carboxylic acid

Question 45

What is the functional group for a carboxylic acid?

Answer 45

C-O double bonds with -OH bonded to C aswell (COOH)

Question 46

What is the functional group of an aldehyde?

Answer 46

C-O double bond

Question 47

What happens in the oxidation of a primary alcohol?

Answer 47

the -OH loses the H and double bonds with the C making the O-C double bond making an aldehyde an -O is then added to the remaining -H making an -OH on the C with the double bonded C-O making a carboxylic acid

Question 48

What is the product of oxidizing a secondary alcohol?

Answer 48

a ketone

Question 49

What is the functional group for a ketone?

Answer 49

C double bonded to O, that C is also single bonded to two other C's

Question 50

What happens in the oxidation of a secondary alcohol?

Answer 50

the -OH loses an -H and the -O forms a double bond with the C, which has two other C-C bonds

Question 51

What is the product of oxidizing a tertiary alcohol?

Answer 51

can't oxidize a tertiary alcohol

Question 52

What is the product of oxidizing a thiol?

Answer 52

disulfide and H2O

Question 53

What happens in the oxidation of thiols?

Answer 53

and -H is lost from each of two -SH groups forming S-S bond and H2O (H from thiols and O from oxidation)