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C Core and Organic Chemistry > Y2 Carbonyls (O) > Flashcards

Y2 Carbonyls (O) Flashcards

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1
Q

Nucleophile definition

A

An electron pair donor

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2
Q

Electrophile definition

A

An electron pair acceptor. Attracted to areas of high electron density

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3
Q

Why do acyl chlorides undergo nucleophilic addition reactions?

A
  • The oxygen and chlorine atoms attached to the carbonyl carbon are electronegative. - - They pull the electrons in the covalent bonds toward them, leaving the carbonyl carbon positive
  • This makes it available for attack by nucleophiles.
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4
Q

What type of reactions do acyl chlorides undergo?

A

Nucleophilic addition elimination

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5
Q

What acyl chloride reactions do you need to know?

A

Reactions with:
- water,
- alcohol (ethanol),
- ammonia,
- a primary amine

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6
Q

What is the product of acyl chloride and each reactant?

A

with water —> carboxylic acid
with alcohol —> ester
with ammonia —> primary amide
with primary amine —> secondary amide (N-subsituted amide)

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7
Q

What is the mechanism for the reduction of a ketone or aldehyde?

A

Nucleophilic addition with NaBH4 (with methanol and water) or LiAlH4 (with dry ether)

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8
Q

ketones and aldehydes can also undergo nucleophilic addition with…?

A
  • A cyanide ion
  • chain length +1
  • hydroxy nitrile formed
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9
Q

What is the nucleophile of nucleophilic addition reactions

A

H(-) /hydride /hydrogen anion

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10
Q

Solubility of carbonyls

A
  • as the length of the chain increases
  • carbonyls become less soluble in water
  • the significance of the polar C=O bond decreases
  • aren’t then dissolved in a polar solvent
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11
Q

Why does ‘like’ dissolve ‘like’?

A

-polar compounds are dissolved by polar solvents as small intermolecular forces between the molecules will be created e.g dipole-dipole bonding and hydrogen bonding.

  • non polar compounds will be disolved in non polar solvents depending on chain length creating v.d.w imf.
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12
Q

Why won’t a non-polar compound dissolve in a polar solvent? e.g hexane in a water solvent

A

as water is polar it is far more likely to undergo hydrogen bonding with other water molecules than bond to hexane.

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13
Q

How many H does one reduction require?

A

2 [H+]

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14
Q

Reactant for oxidation

A

Potassium dichromate (K2Cr2O7) and dilute H2SO4

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15
Q

colour change of potassium dichromate

A

orange Cr(6+) to green Cr(3+) colour change

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16
Q

Reactant for reduction

A

NaBH4 (sodium borohydride) or LiAlH4 (lithium aluminium hydride)

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17
Q

What to Tollen’s and Fehlings solution indicate?

A

aldehyde is present ( as can be partially oxidised further but ketones can’t)

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18
Q

Fehling’s solution colour change

A

Blue Cu(2+) ions –> brick red ppt Cu2O

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19
Q

Tollen’s reagent colour change

A

colourless –> silver mirror
[Ag(NH3)2]+ complex ions form metallic Ag+ (silver)

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20
Q

What two Nucleophilic addition reactions happen with ketones and aldehydes?

A

Reduction with cyanide or hydride ion

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21
Q

If undergoing Nucleophilic addition of a carbonyl with cyanide ion

A

Hydroxy nitrile produced will be an optically active isomer. And form two enantiomers with a chiral carbon.
- Watch out for it! Think

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22
Q

Why are racemates formed in equimolar ratios (50:50)?

A
  • Attacks onto a planar molecule at the carbon
  • There is equal opportunity of the cyanide ion attacking above or below the plane
  • Therefore, enantiomers and racemates are formed
  • Results in a trigonal planar molecule
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23
Q

What are all reducing sugars?

A

Aldehydes

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24
Q

What are all non-reducing sugars?

A

Ketones

25
Q

Glucose

A
26
Q

Mechanism for Nucleophilic addition elimination reaction of cyanide with ketones and aldehydes

A
27
Q

Mechanism for Nucleophilic addition elimination reaction of hydride with ketones and aldehydes

A
28
Q

Oxidation of primary secondary tertiary alcohols

A
29
Q

Solubility of carboxylic acids

A
30
Q

What is a dimer?

A
31
Q

Acidity of carboxylic acids

A
32
Q

Test for carboxylic acids

A
33
Q

Carboxylic acid with carbonates

A
34
Q

Why do Carboxylic acids dissolve in water?

A
35
Q

Reduction of carboxylic acids

A
36
Q

Estérification

A
37
Q

What are the reactants in estérification?

A

Carboxylic acid and alcohol

38
Q

Naming esters

A
39
Q

Uses of esters

A
40
Q

Hydrolysis (reverse estérification)

A
41
Q

Why are esters good solvents

A

They have low boiling points and are good polar solvents

42
Q

Glycerol

A
43
Q

Glycerol IUPAC name

A

Propane-1,2,3-triol

44
Q

Triglyceride esters

A
45
Q

Saponification of oils and fats makes

A

Glycerol and sodium carboxylate salts

46
Q

What is the most important part to remember in production of vegetable oils and fats

A

The THREE molecules of water produced!!

47
Q

What is biodiesel

A
48
Q

How do soaps work?

A
49
Q

Transesterification

A
50
Q

Carboxylic acid derivatives

A
51
Q

Acid anhydride NAE reactions reactants and products

A

Alcohol —> Ester + c. Acid
Water —> 2 c. Acid
Ammonia —> primary amide + c. Acid
Primary amine —> N. Sub amide + c. Acid

52
Q

Conditions for Nucleophilic addition elimination of acyl chlorides and acid anhydrides

A

Room temp and anhydrous except for when reacting with water, obviously

53
Q

Acyl chloride Nucleophilic addition elimination reactions

A
54
Q

3 possible reactions in the manufacturing of aspirin

A
55
Q

Which is the best reactant to use with salicylic acid in the manufacturing of aspiring? And reasons

A

Ethanoic anhydride

56
Q

Aspirin

A
57
Q

Nucleophilic addition elimination mechanism

A
58
Q

Acid anhydrides

A

C Core and Organic Chemistry (19 decks)

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