Carboxylic acids Flashcards

1
Q

What is the prefix for carboxylic acids?

A

anoic acid

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2
Q

What is the prefix for a compound with 2 carboxylic acid func groups?

A

dioc acid

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3
Q

What state are carboxylic acids at room temp?

A

liquid

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4
Q

Which has a higher BP an alcohol or a carboxylic acid? and why?

A

higher in a carboxylic acid = carboxylic acid is more polar than alcohol so permenant d-d forces
and carboxylics have a structure which allows them to form more H bonds

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5
Q

Are carboxylic acids soluble in water?

A

yes = they form H bonds

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6
Q

What affects the solubility of carboxylic acids in water?

A

the longer the hydrocarbon chain, solubility decreases = it is non-polar
this can outweigh the polar OH group

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7
Q

Are carboxylic acids strong or weak acids?

A

weak = only slightly soluble in aq solution

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8
Q

What is a derivative?

A

a compound in which the functional group of a compound is converted into something different

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9
Q

What are all the derivatives of carboxylic acids?

A

esthers
acyl chlorides
acid anhydrides
amides

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10
Q

What is the functional group of esthers?

A

RCOOR

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11
Q

What is the name ending for esthers?

A

anoate

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12
Q

Do esthers have a lower or higher MP and BP than carboxylic acids?

A

lower
esthers only form permanent d-d and induced
carboxylic acids form H bonds

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13
Q

How can you make an esther from a carboxylic acid? What is the process called?

A

Esterification of a carboxylic acid with an alcohol
adding an alcohol to a carboxylic acid
condensation reaction

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14
Q

What is the general reaction of esterification of a carboxylic acid with an alcohol?

A

carboxylic acid + alcohol —> ester + water

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15
Q

What type of reaction is esterification?

A

condensation = water molecule is removed

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16
Q

What are the conditions for esterification?

A

conc H2SO4 and heat
reflux

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17
Q

What are acid anhydrides?

A

compunds formed by the dehydration of carboxylic acids

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18
Q

What is the general formula of acid anhydrides?

A

RCOOCOR

Carbon double bonded to an O with an R group
bonded to an O that is bonded to another Carbon double bonded to an O with an R group

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19
Q

How do you name acid anhydrides?

A

anoic anhydride

20
Q

How is an acid anhydride formed?

A

formed from 2 carboxylic acids by the elimination of water

21
Q

How do you form an ester from an acid anhydride?

A

anhydride and alcohol makes an ester and carboxylic acid

22
Q

what is the equation reacting an acid anhydride with an alcohol?

A

anhydride + alcohol —> ester + carboxylic acid

23
Q

What is the condition for reacting an acid anhydride with an alcohol?

A

gentle heat
no catalyst

24
Q

What are the advantages of producing esters from acid anhydrides rather than carboxylic acids?

A

milder conditions = stong acid catalyst needed for carboxylic reaction which might cause further reaction of other functional groups

reaction with acid anhydrides is irreversible = easier to get a higher yield of ester using anhydride

25
Q

What is a hydrolysis reaction?

A

a reaction which a compound is broken down by addition of a water molecule

26
Q

What reacts with an ester in base catalysed hydrolysis?

A

NaOH - for OH-

27
Q

What does base catalysed hydrolysis form?

A

alcohol and the salt of the carboxylic acid

28
Q

What are the conditions of base hydrolysis of an ester?

A

refulx with aq NaOH

29
Q

Why is base catalysed hydrolysis better than hydrolysing a ester with water?

A

irreversible reaction so it gives higher yields

30
Q

How do you convert the carboxylic salt into its carboxylic acid?

A

neutralise with aq acid
distill off the carboxylic acid

31
Q

What are the 2 types of hydrolysis?

A

acid catalysed
base catalysed

32
Q

What are the products of base catalysed hydrolysis?

A

salt and alcohol

33
Q

Why does acid catalysed hydrolysis produce a lower yield?

A

it is reversible

34
Q

What are the conditions for acid catalysed hydrolysis?

A

reflux with aq HCl

35
Q

What are the uses of esters?

A

simple (low mr) esters are volatile and have pleasant, fruity smells which are used in flavourings and perfumes

36
Q

What are acyl chlorides?

A

carboxylic derivative which the OH group is replaced with a Cl

37
Q

How do you name acyl chlorides?

A

oyl chloride

38
Q

How do you make acyl chlorides?

A

use the parent carboxylic acid with SOCl2

39
Q

What is SOCL2 called?

A

thionyl chloride

40
Q

Why are acyl chlorides used in synthesis?

A

they are very reactive because the chlorine readily leaves as Cl- to be replaced by other groups

41
Q

What are the 2 reactions of acyl chlorides you need to know?

A

Friedel-Crafts acylation - halogen carrier and aromatic compound
adding an alcohol to form an ester

42
Q

How can esters be made from acyl chlorides?

A

add an alcohol to form ester and HCl

43
Q

What are the advanatges of making on ester from acyl chloride than estrifying a carboxylic acid?

A

reaction with acyl chlorides happens more rapidly
no catalyst needed and no heat
high yield
used to esterify phenols which will not directly react with carboxylic acids to form phenol esters6+

44
Q

How can acyl chlorides be converted into carboxylic acids?

A

add water to acyl chloride to produce carboxylic and HCl

45
Q

How can acyl chlorides form amides?

A

acyl chlorides react with ammonia to make amines to make amides

46
Q

How is a carboxylic acid formed from a base hydrolysis of an ester?

A

add H+ to the salt

47
Q

How do you remove a carboxylic acid from a solution?

A

if its a solid = it will precipitate out
if its oil = will form a layer of oil which needs to be separated using a separating funnel
if it’s a liquid = distillation