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Carbonyl/Isomerism

AQA A Level Chemistry

QuestionAnswer
What are the two main types of isomerism? Structural isomerism and stereoisomerism
What are the three types of structural isomerism? Chain isomerism, position isomerism, functional group isomerism
What are the two types of stereoisomerism? Geometric isomerism and optical isomerism
Which organic molecules demonstrate optical isomerism? Ones containing chiral carbons
How can chiral carbons be identified? Carbon atoms with four different groups surrounding them
What are enantiomers? Molecules with the same structural formula but exhibiting optical isomerism
How do enantiomers differ in terms of their mirror images? They are non-superimposable upon their mirror images
How do enantiomers differ in terms of their effect on plane polarized light? They rotate it in opposite directions
What is a racemic mixture? A 50:50 mixture of two enantiomers
Explain the effect of a racemic mixture on plane polarized light One enantiomer rotates the light clockwise and the other anti-clockwise, resulting in no net rotation.
Which homologous series are considered "carbonyls"? Aldehydes and ketones
How can aldehydes and ketones be distinguished? Fehling's solution or Tollen's reagent
How can aldehydes be formed? Oxidation of a primary alcohol or reduction of a carboxylic acid
How can ketones be formed? Oxidation of a secondary alcohol
Name the reagent and conditions for the reduction of carbonyl compounds NaBH₄, aqueous
How is the reductant represented in equations? [H]
What is the name of the mechanism for the reduction of carbonyls? Nucleophilic addition
Draw a mechanism for the reduction of a given carbonyl Draw
Under which conditions are hydroxynitriles formed? Addition of KCN followed by dilute acid to a carbonyl
Draw a mechanism for the reaction of KCN with a given carbonyl Draw
Explain how nucleophilic additions of carbonyls with KCN can result in a racemic mixture Carbonyl is planar, KCN can attack from above or below with equal probability, 50:50 chance of forming each enantiomer
Which hazards are associated with using KCN? It is highly toxic
Write an overall equation for the formation of a given hydroxynitrile with HCN Draw
Why do aldehydes and ketones have higher boiling points than alkanes with the same number of carbon atoms? The carbonyl bond means that there are permanent dipole dipole interactions between the molecules which are not present between the alkane molecule
Why do aldehydes and ketones have lower boiling points than alcohols with the same number of carbon atoms? There is hydrogen bonding between the alcohol molecules. This is a stronger intermolecular force than the dipole dipole attractions between the carbonyl compounds
Why are small carbonyl compounds miscible in water? The formation of hydrogen bonds from the water to the oxygen of the carbonyl compound.
Why is the carbonyl bond polar? The difference in electronegativity between carbon and oxygen
What is the difference in structure between an aldehyde and ketone? "ALDEHYDES have at least one H attached to the carbonyl group. Ketones have two carbons attached to the carbonyl group.
Name this molecule CH3CH2COCH2CH3 "pentan-3-one
Draw the structural formulae of this molecule phenylethanone Draw
Explain in detail the technique recrystallization. Dissolve the solute in the minimum volume of hot solvent, cool the solution to allow the crystals to form, remove the crystals by vacuum filtration, dry the resulting crystals in an oven.
What measurement of a substance is the best measure of its purity Melting Point
Give the name of a suitable reducing agent for the reduction of a carbonyl compound to an alcohol. Lithium Tetrahyridoaluminate, Sodium Tetrahydridoborate
What is the nucleophile produced by NaBH4 and LiAlH4? H-
"Draw the mechanism for the reduction of butanal to butanol Draw
"Why is Propanoyl chloride more easily reduced by Hydride ions than Propanal. Chlorine are more electronegative than carbon, Atoms attached to the carbonyl carbon that are more electronegative than carbon make it more delta positive (1) More delta positive the carbonyl carbon is the more reactive it is, towards nucleophiles such as
What are the reagents for the nucleophilic addition of cyanide ions to aldehydes or ketone? "hydrogen cyanide - HCN in the presence of KCN
What are the conditions for the nucleophilic addition of cyanide ions to aldehydes or ketone? "reflux in alkaline solution
What is the structural formula of the product of the reaction of these two molecules CH3CHO + HCN "CH3CH(OH)CN
Draw out the mechanism for the reaction between these two molecules CH3CHO + HCN Draw
Created by: JBearfield