Optical isomerism and carbonyl compounds

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20 Terms

1
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Define stereoisomers

Same structural formula atoms arranged differently

2
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What is a chiral carbon

Carbon with 4 different atoms/groups attached

Tetrahedral arrangement is possible so that one mirrors another l

3
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How do you distinguish between aldehydes and ketones 

Tollens reagent-colourless silver nitrate dissolved in aqueous ammonia 

[Ag(NH3)2]+

If heated with aldehyde = silver mirror 

Fehlings solution 

Blue complex copper ions dissolved in NAOH 

If aldehyde brick red precipitate

4
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How do you form hydroxy nitriles (two reagents)

Nucleophillic addition 

KCN + aldehyde/ketone 

Followed by dilute acid 

If HCN no acid needed because H+,dangerous slow

5
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Explain why hydroxynitriles produces a racemic mixture 

Carbonyl group is planar

Nucleophile can attack on either side with equal probability 

To produce racemic mixture 

Equal amounts of to enatiomers 

6
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Define racemic mixture

Equal mixture of both enatiomers

7
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Describe how separate samples of each of these enatiomers could be distinguished 

Use plane polarised light 

See if they rotate light in opposite directions 

8
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How do you reduce aldehydes/ketones and what do they produce 

Sodium tetrahydrideoborate

NaBH4

Aldehydes =reduced to primary alcohols 

Ketones = secondary alcohols 

9
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Hazards of KCN

Toxic 

Fume cupboard

Risk of HCN gas released from solution

Heat in water bath as organic compounds flammable

10
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Why does compound NOT show sterioisomerism

No chiral centre

Not 4 different groups attached to carbon 

11
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By considering the mechanism (reduction with NaBH4) explain why the product has no effect on plane polarised light 

Nucleophile attacks compound 

Carbonyl group planar

H- attacks from either side with equal probability 

exists in two chiral forms 

Racemic mixture /equal amounts of each 

Enatiomers rotate plane polarised light equally

So effects cancel 

12
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State relationship between two chiral molecules with the same structural formula 

Non superimposable mirror images 

13
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How to test for carboxylic acid+observations

React with carbonate (caco3/naco3/nahco3)

Effervescence -bubbles of co2

14
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What is the relationship between solubility and carboxyllic acid chain length

R group length increases

Less soluble 

More hydrocarbon chain which is non polar so does not form hydrogen bonds 

15
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What reaction forms an esters 

Esterification 

Reaction between carboxyllic acid and alcohol 

Concentrated H2SO4 catalyst 

Reversible 

16
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Uses of esters 

Solvents 

Plasticiser -weaken IMF polymer chains making them flexible 

Food flavourings +perfume 

17
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What do you form from acid/base hydrolysis  of ester

Acid-carboxylic acid 

Base-carboxylate ions (non reversible higher yield ,reflux

18
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