Carbonyls Flashcards

1
Q

what is the difference between an aldehyde and a ketone

A

an aldehyde has just one carbon bonded to the oxygens carbon ( it is at the end of the chain)

a ketone has 2 carbons bonded to the oxygens carbon (in middle of a chain)

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2
Q

what allows carbonyls to do hydrogen bonding

A

dipole with electronegative oxygen and carbon

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3
Q

why cant carbonyls have a hydrogen bond to them

A

no hydrogens present

(they still can bond to water )

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4
Q

why is mp of carbonyls less than alcohols

A

carbonyls cannot bond with themselves unlike alcohols so less h bonding and also less electrons in molecule means weaker london forces.

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5
Q

how do smaller aldehydes and ketones hydrogen bond

A

lone pairs on oxygen
very electronegative
can form H bonds with the positive hydrogens in water

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6
Q

why cant larger carbonyls hydrogen bond

A

long hydrocarbon chains disrupt hydrogen bonding within water and the hydrocarbons cannot form H bonds themselves

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7
Q

why cant the larger carbonyls dissolve in water

A

no hydrogen bonds can form

in order to dissolve the strength of hydrogen bonds must be higher than the combined strength of all IM forces present.

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8
Q

reaction from aldehyde to carboxylic acid

A

aldehyde and potassium dichromate —–> carboxylic acid

WILL NOT WORK WITH KETONE

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9
Q

why can ketones be oxidised

A

do not have a readily available hydrogen atom
oxidation of a ketone would need a very strong oxidising agent and if this was present it would just break the ketone down anyway.

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10
Q

what colour does aldehyde go upon adding potassium dichromate

A

orange to green

ketone stays orange

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11
Q

what happens when aldehyde heated with tollens

A

oxidised to carboxylic acid

silver complex ion in the tollens is reduced to silver.

producing a silver mirror

no change in ketone

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12
Q

what if an aldehyde is heated with fehlings solution

A

aldehyde will be oxidised
fehlings has copper ions which are reduced to cu2+ from Cu+

brick red colour Cu2+

no change in ketones

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13
Q

aldehydes vs ketones reduction

A

ketones reduced to secondary alcohols, aldehydes primary.

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14
Q

what is reduction of a ketone an example of

A

nucleophilic addition

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15
Q

addition of HCN to carbonyl compound

nucleophilic addition mechanism

A

HCN has hydrogen broken off

CN attacks the carbonyls carbon atom.

breaks double bond and leaves an o- on the carbonyl

the o- bonds with a H+ ion left over from the HCN

results in hydroxynitrile being formed.

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16
Q

what precipitate does iodoform make wwith methyl ketones

A

yellow
because both the iodoform and methyl ketones contain a CH3CO- group

17
Q

halogenation and hydrolysis to heat an iodoform with an alkaline solution of iodine

A

ethanal —> triiodoethanal —–> sodium salt + triiodomethane

1st arrow is halogenation

2nd is hydrolysis

18
Q

what other compound will form a yellow precipitate in iodoform

A

alcohols containing a R-CH(OH)-CH3 group