C17 Organic Chem 2 Flashcards
Optical isomerism point
- chiral centre with 4 different groups attached to it
- forms 2 enantiomers which rotate plane polarised monochromatic light in different directions and are mirror images
- optically active
What is a racemic mixture
Contains 50:50 ratio of both enantiomers of a chiral compound
Do racemic mixtures rotate plane polarised light?
No duh
Optical activity can affect which reaction
Nucleophilic substitution SN2 only though cos in SN1 the nucleophile always attacks the opposite side to the leaving group
Can aldehydes and ketones form hydrogen bonds with themselves?
No
Can aldehydes and ketones form hydrogen bonds with water
Yes, but only if small because when large, the H bonds between water would be stronger than between aldehyde/ketone and water
Tests for aldehyde
Tollen’s Reagent
Fehling’s/ Benedicts
Acidified Dichromate
Tollen’s Reagent
Silver mirror
Heat
Fehling’s / Benedict’s
Blue to Brick red precip.
Acidified dichromate
Orange to Green
Aldehyde to primary alcohol
LiAlH4 in dry ether
Nucleophilic addition
Ketone to secondary alcohol
LiAlH4 in dry ether
Nucleophilic addition
Aldehyde/Ketone to Hydroxynitrile
KCN in HCN/ just HCN
Nucleophilic addition
Why is KCN used instead of HCN often in nucleophilic addition
Because HCN is a highly toxic gas so we do this to reduce risk
Test for a carbonyl group in Aldehyde and Ketone
Add 2,4 DNPH
Forms an orange precipitate
Recrystallise to purify the precipitate
Measure the melting point and compare with the data booklet values
Test for Ketone
(+ ethanal)
Add iodine and alkali
Yellow precipitate and antiseptic smell
Carboxylic acid + Water
Carboxylate ion and H+
Can carboxylic acids dissolve in water
Yes, but not large ones
Nitrile to Carboxylic acid
Dilute HCl and water
Reflux, distillation
Hydrolysis
Carboxylic acid + Base
Salt + water
Acid + Carbonate
Salt + CO2 + H2O
Carboxylic acid to Alcohol
LiAlH4 in dry ether
Reduction
Carboxylic acid to Acyl Chloride
PCl5
CH3-C - O - CH2 CH2 CH3
||
O
Propyl ethanoate
Carboxylic acid to Ester
Alcohol in acid catalyst e.g. H2SO4
Reflux
Distillation just before 80 degrees Celsius
Reversible
Esterification
Ester to Carboxylic Acid + Alcohol
Water
Dilute NaOH
Reflux
Ester to —oate
Dilute alkali
Reflux
Polyester
Dicarboxylic acid and diol
Acyl chloride to Carboxylic Acid
Water
RTP
Acyl chloride to Ester
Alcohol
RTP
Acyl chloride to N substituted amine
Primary Amine
RTP
Acyl chloride to Amide
Conc. ammonia
RTP