chapter 26 Flashcards

(66 cards)

1
Q

secondary alcohols are oxidized to? and under what conditions

A

ketones
refluxed under acidified conditions

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2
Q

the oxidizing agent in the oxidization of secondary alcohols

A

potassium dichromate

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3
Q

primary alcohols are oxidized to what, and under what conditions
oxidizing agent?

A

aldehydes
distilled under acidic conditions
potassium dichromate

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4
Q

can tertiary alcohols be oxidised

A

no

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5
Q

what group is present in the structure of both aldehydes and ketones

A

a carbonyl group

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6
Q

the position of the carbonyl group in a ketone and aldehyde

A

in a ketone, the carbonyl group is joined to two different carbons in the chain, while in aldehydes, the carbonyl group is found at the end of the carbon chain

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7
Q

the ending of a molecular structure of an aldehyde

A

CHO

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8
Q

aldehydes are oxidized to

A

carboxylic acids

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9
Q

conditions for the oxidization of aldehydes and the oxidizing agent

A

reflux under acidic conditions
potassium dichromate

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10
Q

when an aldehyde is oxidized, there is a color change in the dichromate solution from

A

orange to green

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11
Q

do ketones undergo oxidization

A

nope

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12
Q

why is the C=O bond polar

A

because of the difference in electronegativity values of O and C

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13
Q

nucleophile

A

a electron donor

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14
Q

aldehydes and ketones can be reduced to
the reducing agent for such reactions?

A

alcohols
sodium tetrahydridoborate (III) (NaBH4)

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15
Q

in nucleophilic addition, the C=O pie bond breaks in a ……………. manner forming a …………….. charged intermediate

A

heterolytic
negatively

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16
Q

in nucleophilic addition, the hydride ion is provided by

A

the NaBH4

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17
Q

Describe what happens in nucleophilic addition

A

lone pair on the hydride ion is attracted and donated to the partially positive carbon atom of the C=O bond. This forms a dative covalent bond

in nucleophilic addition, the C=O pie bond breaks in a heterolytic manner forming a negatively charged intermediate

the oxygen atom in C-O bond in the intermediate donates a lone pair of electrons to a hydrogen atom in a water molecule.

An alcohol is formed as a result

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18
Q

an aldehyde reacts with hydrogen cyanide to form
under what conditions
where do we get the hydrogen cyanide from

A

a hydroxynitrile
acidic conditions
NaCN

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19
Q

why is the reaction between an aldehyde and hydrogen cyanide important

A

it provides a way to extend the carbon chain length

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20
Q

on which atom is the lone pair in CN on

A

on C

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21
Q

brady’s reagent

A

a solution of 2,4-DNP dissolved in methanol and sulfuric acid

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22
Q

describe a test to identify a carbonyl group in either an aldehyde and a ketone

A

add a 5cm depth of a solution of 2,4-DNP to a clean test tube
add 3 drops of the unknown compound. leave to stand
a yellow/orange precipitate forms if there is a carbonyl group(aldehyde or ketone) present

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23
Q

if no crystals form when brady’s reagent is added to a solution containing a ketone or an aldehyde

A

add more sulfuric acid

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24
Q

how do we identify whether a carbonyl group is exactly in a certain molecule

A

the precipitate formed after adding Brady’s reagent is filtrated
then it is recrystallized
the melting point is then measured and compared with known values

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25
tollen's reagent
a solution of silver nitrate in aqueous ammonia
26
in the tollen's reagent, what acts as the oxidizing reagent
Silver ions
27
an aldehyde is oxidized to
a carboxylic acid
28
if an aldehyde is present in the tollen's reagent test, what happens
a silver mirror is formed
29
will the tollen's reagent be able to identify ketones and why
no, because ketones cannot be oxidized further
30
if there are two carboxylic acids in a compound, the name changes to the corresponding alkane, with a............ added at the end
dioic acid
31
carboxylic acids can form hydrogen bonds with two compounds, what are these
water and other carboxylic acids
32
name the factor that decreases the solubility of carboxylic acids
an increase in the number of atoms in the non polar carbon chain
33
what happens to the solubility of carboxylic acids as the acid group(COOH) increases
the solubility increases further
34
carboxylic acids with up to 4 carbon atoms are all soluble in water, true or false
true
35
are carboxylic acids strong acids?
no they are rather weak acids
36
products formed when carboxylic acids react with metals
salt and hydrogen gas
36
products formed when carboxylic acids react with metals
salt and hydrogen gas
37
carboxylic acids react with metal carbonates to form
salt, water and carbon dioxide
38
carboxylic acid derivatives
compounds that can be hydrolysed to form the parent carboxylic acid
39
in hydrolysis, which bond breaks in a carboxylic acid derivative
the single bond between the carbon in the acyl group and a different group
40
suffix for acyl chlorides
oyl chlorides
41
how are acyl chlorides prepared
by reacting carboxylic acids with thionyl chloride
42
molecular formula of thionyl chloride
SOCl2
43
what are the products formed from the reaction of carboxylic acids with thionyl chloride
an acyl chloride, Sulphur dioxide and HCl gas Both gases are toxic
44
acyl chlorides are very unreactive, true or false
false they are very reactive
45
acyl chlorides react by losing ....?
their chloride ion while retain the C=O bond
46
nucleophile
an electron pair donor
47
condensation reaction
a reaction in which two molecules react together to form a larger molecule with the elimination of a small molecule
48
acyl chlorides react with alcohols or phenols to form
an ester and HCl
49
acyl chlorides react with water to form
an carboxylic acid and HCl
50
why should the reaction between acyl chlorides and water be carried out under anhydrous conditions
because if not, the acyl chloride will react violently with water to form the carboxylic acid
51
acyl chlorides react with ammonia to form
Primary amide
52
acyl chlorides react with amines to form
a secondary amide
53
how are acid anhydrides formed
from the condensation reaction between two molecules of carboxylic acid
54
which is more reactive, an acyl chloride, or an acid anhydride
acyl chlorides therefore acid anhydrides are more likely to be used in lab preparations while acyl chlorides might be too reactive
55
acid anhydrides react with alcohols to form
an ester and a carboxylic acid
56
functional group of esters
RCOOR R stands for a carbon group
57
esters are named from backwards to forwards, true or false
true
58
esterification
the reaction of a carboxylic acid with an alcohol to form an ester and water
59
can carboxylic acids react with phenols to form esters
no they cannot, because they are not reactive enough to do so. instead acyl chlorides and acid anhydrides are used
60
do esters react with acyl chlorides
no
61
acid hydrolysis of esters is the reverse of
esterification
62
in acid hydrolysis, the ester is heated under .................. with ..........................
reflux dilute aqueous acid
63
in acid hydrolysis, the ester reacts slowly with water. but the reaction is sped up by ........................ what acts as the catalyst
catalysis the dilute aqueous acid
64
alkaline hydrolysis is also known as
saponification
65
in alkaline hydrolysis, the ester is heated under............... with .................. to form a ......................... and an ...................
reflux aqueous hydroxide ions carboxylate ion alcohol