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semester 2 chemistry revisions > Lecture 11 > Flashcards

Lecture 11 Flashcards

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1
Q

What reaction do Aldehydes/ Ketones undergo?

A

Nucleophilic Addition

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2
Q

Which one Aldehydes/ Ketones can be further oxidised?

A

Aldehydes

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3
Q

What is the functional group on an aldehyde? Where is it located?

A

CHO

End of Carbon Chain

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4
Q

What is the functional group on an ketone? Where is it located?

A

C–O

Middle of Carbon Chain

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5
Q

What is Formaldehdye?

What can it be used todo? (2)

A

Manufactured for Methanol- Methanal
Changes the structure of proteins via crosslinking.
Used to form polymers

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6
Q

What is acetaldehyde?

A

Ethanal
Prepared from ethyl alcohol
Detoxification of alcohol in liver (hangover).

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7
Q

What is acetone? When is it formed in the human body?

A

Simplest ketone- Propanone

by product of lipid metabolism,. Excreted in urine and breath.

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8
Q

In carbonyl compounds what hybridisation is the Carbon and Oxygen?
How is the sigma bond formed?
How is the pie bond formed?

A

Sp2 hybridised.
OVERLAP of sp2 ORBITALS of Carbon and Oxygen.
OVERLAP of UNHYBRIDIZED P ORBITALS.

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9
Q

What is the bond angel at carbon?

A

120o

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10
Q

How do you name aldehydes?

  • IUPAC
  • COMMON
A

IUPAC: Alkane name with ‘e’ removed and replaced with ‘al’.

COMMON NAMING: Deprived from the names of carboxylic acids by replacing ‘ic acid’ by ‘aldehyde’.

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11
Q

BUTANAL

A

Butyraldehyde

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12
Q

How do you name ketones?

  • IUPAC
  • COMMON
A

Alkane name with ‘e’ removed and replaced with ‘one’. The location of the group in the chain is indicated by the number before the -one.
The word ketone is added after the alkyl groups attached to the carbonyl group.

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13
Q

BUTAN-2-ONE

A

Methyl ethyl ketone (MEK)

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14
Q

When oxidising primary alcohols what is in excess? Why?

A

EXCESS alcohol- There is not enough oxidising agent to oxidise the primary alcohol to a carboxylic acid, so will be oxidised to an aldehyde instead.

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15
Q

Reagents/ Conditions for oxidising primary alcohols to an aldehyde?

A

Acidified K2Cr2O7 under distillation or Pyridinium Chlorochromate (PCC).

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16
Q

How do you know when PCC has oxidised the reaction?

A

Goes from an orange powder to a black sticky gunk.

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17
Q

Reagents for oxidising primary alcohols to an aldehyde in the body?

A

Alcohol dehydrogenases + NAD(P)+ (accepts H- and Zinc factor is needed to hold everything together in the active site).

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18
Q

What reagent is needed in the oxidation of methylarmotic to an alkylbeneze.

A

H+/ Na2Cr2O7

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19
Q

What are the reagents used in the reduction of acid chlorides?
Why are acid chlorides used in this reduction reaction?

A

LiAlH(OtBu)3 or H2, Pd-BaSO4

Derivative of a carboxylic acid. Carboxylic acid would reduce straight to alcohol.

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20
Q

Oxidation or secondary alcohols- product?

Reagent/ Conditions?

A

Ketone
Acidified K2Cr2O7
Conditions make no difference to the product.

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21
Q

What reaction type is FRIEDEL CRAFTS ACYLATION?

A

ELECTROPHILIC SUBSTITUTION

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22
Q

What is the reagent needed in FRIEDEL CRAFTS ACYLATION?

A

AlCl3

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23
Q

What organometallic reagent is needed to couple with a carboxylic acid derivative? Why is this reagent used?

A

Organocuprate- C-Cu (Ionic bond).

Less reactive so needs to be a controlled reaction to get a ketone instead of a tertiary alcohol.

24
Q

What is the biological equivalent of a thioester?

A

Acyl Chloride

25
Q

What affects the boiling point of a carbonyl compound?

A

Carbon- Oxygen double bond- POLAR

26
Q

Boiling point of carbonyl compounds are HIGHER than .. and LOWER than …. Why?

A

HIGHER than ethers (C-O bonds).

LOWER than alcohols (hydrogen bonding). Aldehydes/ Ketones cannot make hydrogen bonds with themselves.

27
Q

What does carbonyl compounds have which are characteristic of them?

A

Strong Smells

28
Q

Carbonyl compounds have similar solubilities to what?

A

Alcohols

29
Q

Why are short chain aldehydes/ ketones soluble in water?

What happens with longer chain aldehydes/ ketones?

A

Short chain aldehydes and ketones are soluble in water because they are able to make Hydrogen bonds. When the length of chain grows HYDROPHOBIC LONDON DISPERSION forces grow so difficult to break these, with only a few Hydrogen bond.

30
Q

Name the 3 reactions which carbonyl compounds can undergo?

A
  1. Nucleophilic Addition
  2. Alpha- Substitution
  3. Condensation
31
Q

Describe Nucleophilic Addition with a Cyanide ion.

A
  1. Cyanide ion attacks the slightly positive Carbon.
  2. The Carbon- Oxygen double bond breaks
  3. Pair of electrons goes to Oxygen.
  4. A pair of electrons is used to form a bond with Hydrogen.
  5. Overall there has been addition of HCN across the double bond.
32
Q

What is a Cyanohydrin?

A

HO-C-C—N

33
Q

What happens in a Cyanohydrin because the C-C is less stable than a normal C-C bond?

A

Spontaneous breakdown of the C-C to release the CN.

34
Q

What is hydration?

A

Addition of water.

35
Q

Name 2 aldehydes which dissolve in

A

Formaldehyde and Acetaldehyde.

36
Q

What forms a hydrate?

A

Dissolving Acetaldehyde.

37
Q

What is a Hydrate?

A

2 OH groups on the same Carbon.

38
Q

When is the reagent needed to produce a semi- acetal/ ketal and acetal/ketal from aldehyde and ketones?
What reaction is this?

A

ROH

Nucleophilic Addition

39
Q

How do you recognise an ‘Atal’?

A

Oxygen cannot be bonded to hydrogen instead bonded to R group (Ether).

40
Q

What is a mixed acetal?

A

Bond between ‘oxygen and nitrogen’ rather than ‘oxygen and oxygen.’

41
Q

What is a tautomer?

A

2 or more ISOMERS of a compound together in an equilibrium mixture.

42
Q

Oxidation of a primary alcohol and secondary alcohol into ….

A

Primary alcohol to aldehyde to carboxylic acid.

Secondary alcohol to ketone to no more oxidation.

43
Q

What is the chemical reagent for the oxidation of primary/ secondary alcohols?

A

H+/ K2Cr2O7 or permanganate oxidising agent.

44
Q

What is the biological reagent for the oxidation of primary/ secondary alcohols?

A

Aldehyde dehydrogenase (ALDH) + NAD(P)+.

45
Q

What reaction is used when testing for sugars? (Reactants/ Products)

A

Aldehyde to Carboxylic Acid

46
Q

What is the Silver Mirror Test made of?

What happens in this test?

A

Tollens Reagent= Silver Nitrate, Aqueous Ammonia, NaOH.

Aldehyde is oxidised so reduced silver.

47
Q

What is Benedicts Solution and Fehling Solution made of?

What happens in this test?

A

Benedict’s Reagent= CuSO4 + alkaline citrate.
Fehling’s= CuSO4 + alkaline tartrate.
Cu2+ is reduced to Cu+.

48
Q

What is a positive result for Benedict’s/ Fehlings Solution?

A

Blue Solution to Brick- Red precipitate

49
Q

What is the chemical reagent for the reduction of an aldehyde/ ketone?

A

Need source of H2 or H+/H-

NaBH4, LiAlH4, Diisobutyaluminimum hybride; H2 and Pd/Pt/ Ni

50
Q

What is the biological reagent for the reduction of an aldehyde/ ketone?

A

NAD(P)H

51
Q

What does the a-substitution involve?

A

Enol or enolate.

52
Q

Describe the a-substitution mechanism.

A
  1. Addition
  2. Condensation
    Aldehyde to aldol to alkene
53
Q

How do you test for ketones?

A

Using a dip stick.

54
Q

What is a positive result?

A

Colourless to Purple (Darkness how many ketones present).

55
Q

In alpha substitution what is the enzyme for carbohydrate metabolism?

A

Aldolases.

semester 2 chemistry revisions (12 decks)

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