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Orgo > Chap 13: Alcohols, Phenols, Thiols, and Ethers > Flashcards

Chap 13: Alcohols, Phenols, Thiols, and Ethers Flashcards

1
Q

What is the functional group of alcohols?

A

hydroxyl, -OH

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2
Q

What is an alcohol?

A

carbon chain with an -OH attached

can by cyclic

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3
Q

What is a phenol?

A

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

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4
Q

What is a thiol?

A

a carbon chain with an -SH attached

can be cyclic

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5
Q

What is the IUPAC naming method for alcohols?

A

change -ane to -anol

e.g. methane into methanol

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6
Q

How to name alcohol with 3+ carbons?

A

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

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7
Q

Naming alcohol with 2 or 3 hydroxyl group?

A

diol
triol
e.g. 1,2-butanediol

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8
Q

Naming cyclic alcohols?

A

named cycloalkanol

if more than one substituent need to # the C

C1 is where the -OH is

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9
Q

Naming phenols?

A

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

after name as usual

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10
Q

What is distinct about thiols?

A

have distinct odors

used to detect gas leaks

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11
Q

Thiols are also known as what?

A

mercaptans

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12
Q

Naming thiols?

A

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

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13
Q

What is an ether?

A

O attached by single bonds to two C atoms

O between two C’s

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14
Q

Can an ether be between alkyls and aromatic rings?

A

yes

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15
Q

Naming ethers?

A

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

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16
Q

How are alcohols classified?

A

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

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17
Q

What are the classifications of alcohols?

A

primary
secondary
tertiary

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18
Q

What is a primary alcohol?

A

only has one alkyl group on -OH C

or has 2 H’s on -OH C

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19
Q

What is a secondary alcohol?

A

has two alkyl groups on -OH C

or has one H on -OH C

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20
Q

What is a tertiary alcohol?

A

has three alkyl groups attached to -OH C

of has no H on -OH C

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21
Q

Which has higher MP/BP alcohols or ethers?

A

alcohols

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22
Q

Why do alcohols have higher MP/BP than ethers?

A

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

23
Q

Ethers have similar MP/BP to what?

A

alkanes

24
Q

Why do alkanes and ethers have similar MP/BP?

A

they are unable to form hydrogen bonds

25
Q

Are alcohols soluble in water?

A

sometimes

26
Q

When are alcohols soluble in water?

A

when it has 1-3 Carbons

27
Q

When are alcohols not soluble in water?

A

when it has 4+ Carbons

28
Q

What makes some alcohols soluble in water?

A

the polar -OH group

29
Q

Are ethers soluble in water?

A

sometimes, but only slightly

30
Q

When are ether able to be soluble in water?

A

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

31
Q

When are ethers never soluble in water?

A

when it has 5+ Carbons

32
Q

What makes some ethers slightly soluble in water?

A

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

33
Q

Are phenols soluble in water?

A

only slightly

34
Q

What allows phenols to be slightly water soluble?

A

the -OH group can form hydrogen bonds with water

35
Q

Phenols can react with water to form what?

A

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

36
Q

What happens in the dehydration of alcohols?

A

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

37
Q

What does the dehydration of an alcohol produce?

A

alkene and H2O

38
Q

What happens in the dehydration of a secondary alcohol?

A

a major and minor product are formed

39
Q

What is the rule for dehydration of secondary alcohols?

A

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

40
Q

What is oxidation?

A

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

41
Q

What is reduction?

A

reduce the number of bonds b/w C-O

42
Q

Which alcohols can be oxidized?

A

primar and secondary

43
Q

Why can’t tertiary alcohols be oxidized?

A

because there is no -H to remove

44
Q

What is the product of oxidizing a primary alcohol?

A

aldehyde which further oxidizes into a carboxylic acid

45
Q

What is the functional group for a carboxylic acid?

A

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

46
Q

What is the functional group of an aldehyde?

A

C-O double bond

47
Q

What happens in the oxidation of a primary alcohol?

A

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

48
Q

What is the product of oxidizing a secondary alcohol?

A

a ketone

49
Q

What is the functional group for a ketone?

A

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

50
Q

What happens in the oxidation of a secondary alcohol?

A

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

51
Q

What is the product of oxidizing a tertiary alcohol?

A

can’t oxidize a tertiary alcohol

52
Q

What is the product of oxidizing a thiol?

A

disulfide and H2O

53
Q

What happens in the oxidation of thiols?

A

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

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