C17 Organic Chem 2 Flashcards

1
Q

Optical isomerism point

A
  • 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
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2
Q

What is a racemic mixture

A

Contains 50:50 ratio of both enantiomers of a chiral compound

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3
Q

Do racemic mixtures rotate plane polarised light?

A

No duh

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4
Q

Optical activity can affect which reaction

A

Nucleophilic substitution SN2 only though cos in SN1 the nucleophile always attacks the opposite side to the leaving group

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5
Q

Can aldehydes and ketones form hydrogen bonds with themselves?

A

No

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6
Q

Can aldehydes and ketones form hydrogen bonds with water

A

Yes, but only if small because when large, the H bonds between water would be stronger than between aldehyde/ketone and water

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7
Q

Tests for aldehyde

A

Tollen’s Reagent
Fehling’s/ Benedicts
Acidified Dichromate

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8
Q

Tollen’s Reagent

A

Silver mirror
Heat

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9
Q

Fehling’s / Benedict’s

A

Blue to Brick red precip.

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10
Q

Acidified dichromate

A

Orange to Green

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11
Q

Aldehyde to primary alcohol

A

LiAlH4 in dry ether
Nucleophilic addition

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12
Q

Ketone to secondary alcohol

A

LiAlH4 in dry ether
Nucleophilic addition

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13
Q

Aldehyde/Ketone to Hydroxynitrile

A

KCN in HCN/ just HCN
Nucleophilic addition

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14
Q

Why is KCN used instead of HCN often in nucleophilic addition

A

Because HCN is a highly toxic gas so we do this to reduce risk

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15
Q

Test for a carbonyl group in Aldehyde and Ketone

A

Add 2,4 DNPH
Forms an orange precipitate
Recrystallise to purify the precipitate
Measure the melting point and compare with the data booklet values

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16
Q

Test for Ketone
(+ ethanal)

A

Add iodine and alkali
Yellow precipitate and antiseptic smell

17
Q

Carboxylic acid + Water

A

Carboxylate ion and H+

18
Q

Can carboxylic acids dissolve in water

A

Yes, but not large ones

19
Q

Nitrile to Carboxylic acid

A

Dilute HCl and water
Reflux, distillation
Hydrolysis

20
Q

Carboxylic acid + Base

A

Salt + water

21
Q

Acid + Carbonate

A

Salt + CO2 + H2O

22
Q

Carboxylic acid to Alcohol

A

LiAlH4 in dry ether
Reduction

23
Q

Carboxylic acid to Acyl Chloride

24
Q

CH3-C - O - CH2 CH2 CH3
||
O

A

Propyl ethanoate

25
Q

Carboxylic acid to Ester

A

Alcohol in acid catalyst e.g. H2SO4
Reflux
Distillation just before 80 degrees Celsius
Reversible
Esterification

26
Q

Ester to Carboxylic Acid + Alcohol

A

Water
Dilute NaOH
Reflux

27
Q

Ester to —oate

A

Dilute alkali
Reflux

28
Q

Polyester

A

Dicarboxylic acid and diol

29
Q

Acyl chloride to Carboxylic Acid

30
Q

Acyl chloride to Ester

A

Alcohol
RTP

31
Q

Acyl chloride to N substituted amine

A

Primary Amine
RTP

32
Q

Acyl chloride to Amide

A

Conc. ammonia
RTP