3.8 Aldehydes and Ketones

1

Propanone can be reduced to form an alcohol. A functional group isomer of the alcohol formed is

CH₃CH₂CH₂OH

CH₃CH₂CHO

CH₃OCH₂CH₃

CH₃COCH₃

3.3.8

3.3.8 & 3.3.7 (part)

1

Which one of the following conversions does not represent a reduction?

propene → propane

propanal → propan-l-ol

propanal → propanoic acid

propanone → propane

3.3.8

3.3.8 & 3.3.7 (part)

1

CH₂O is the empirical formula of

methanol

methyl methanoate

ethane-1,2-diol

butanal

3.1.2.4

3.3.8

1

Which one of the following does not represent an oxidation?

propene → propane

propan-l-ol → propanal

propan-l-ol → propanoic acid

propanal → propanoic acid

3.3.5.2 & 3.3.1.2 (part)

3.3.8

1

Which one of the following reactions involves nucleophilic addition?

CH₃CH = CH₂ + HBr → CH₃CHBrCH₃

CH₃CH₂CH₃ + Cl₂ → CH₃CHClCH₃ + HCl

CH₃CH₂CH₂Br + NaOH → CH₃CH₂CH₂OH + NaBr

CH₃CH₂CHO + HCN → CH₃CH₂CH(OH)CN

3.3.8

3.3.8 & 3.3.7 (part)

1

Which one of the following isomers is not oxidised under mild reaction conditions?

(CH₃)₂CHCH(OH)COCH₃

(CH₃)₂C(OH)CH₂COCH₃

(CH₃)₂CHCH(OH)CH₂CHO

(CH₃)₂C(OH)CH₂CH₂CHO

3.3.5.2 & 3.3.1.2 (part)

1

Which one of the following is not a suitable method for the preparation of ethanol?

oxidation of ethane

hydration of ethene

reduction of ethanal

hydrolysis of bromoethane

3.3.5.1 & 3.3.1.2 (part)

3.3.8

1

How many structural isomers, which are aldehydes, have the molecular formula C₅H₁₀O?

2

3

4

5

3.3.1.3

3.3.8

1

Which one of the following will undergo nucleophilic addition?

hex-3-ene

hexan-3-one

3-bromohexane

hexan-3-ol

3.3.8

3.3.8 & 3.3.7 (part)

1

Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

2-methylbutan-1-ol

2-methylbutan-2-ol

3-methylbutan-1-ol

3-methylbutan-2-ol

3.3.8

3.3.8 & 3.3.7 (part)

1

On reduction, a racemate can be formed by

CH₃CH₂CH₂CH₂CHO

CH₃CH₂CH₂COCH₃

CH₃CH₂COCH₂CH₃

CH₃CH=CHCH₂CHO

3.3.8

3.3.8 & 3.3.7 (part)

1

Which one of the following statements about but-2-enal, CH₃CH=CHCHO, is not true?

It has stereoisomers

It shows a strong absorption in the infra-red at about 1700 cm−1

It will turn an acidified solution of potassium dichromate(VI) green

It can be dehydrated by concentrated sulphuric acid

3.3.8

3.3.8 & 3.3.7 (part)

1

Which one of the following reactions will produce an organic compound that has optical isomers?

dehydration of butan-2-ol by heating with concentrated sulphuric acid

reduction of pentan-3-one by warming with NaBH4

addition of Br₂ to 3-bromopropene

reduction of 2,3-dimethylpent-2-ene with H₂ in the presence of a nickel catalyst

3.3.8

3.3.8 & 3.3.7 (part)

1

In which one of the following mixtures does a redox reaction occur?

ethanal and Tollens’ reagent

ethanoyl chloride and ethanol

ethanal and hydrogen cyanide

ethanoic acid and sodium hydroxide

3.1.7

3.3.8

1

Which one of the following would not reduce an acidified aqueous solution of potassium dichromate(VI)?

CH₃COOH

Zn

CH₃CHO

Fe²⁺_(aq)

3.1.7

3.3.8

1

Which one of the following can act as an oxidising agent but not as a reducing agent?

CH₃CHO

Fe²⁺

I⁻

MnO4^-

3.1.7

3.3.8

1

Part a: Butanone is reduced in a two-step reaction using NaBH₄followed by dilute hydrochloric acid.
Write an overall equation for the reduction of butanone using [H] to represent the reductant.

3.3.8

3.3.8 & 3.3.7 (part)

6

Part B: By considering the mechanism of the reaction, explain why the product has no effect on plane polarised light.

3.3.8

3.3.8 & 3.3.7 (part)

3

Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.
Reagent:
Conditions:
Type of reaction:

3.3.5.2 & 3.3.1.2 (part)

3.3.8

1

Propanal is an isomer of propanone. Draw the structure of propanal

3.3.1.3

3.3.8

3

A chemical test can be used to distinguish between separate samples of propanone and propanal. Give a suitable reagent for the test and describe what you would observe with propanone and with propanal.
Test reagent _______________________________
Observation with propanone _
Observation with propanone _____________________

3.3.6.1

3.3.6.2 (O12)

3.3.8

1

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propanal + NaBH₄ -->

3.3.8

3.3.8 & 3.3.7 (part)

1

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propan-1-ol + H₂SO₄ / K₂Cr₂O₇ distilling off the product

3.3.8

3.3.8 & 3.3.7 (part)

1

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanal + Tollen’s reagent with heating

3.3.8

3.3.8 & 3.3.7 (part)

1

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanone + NaBH₄

3.3.8

3.3.8 & 3.3.7 (part)

1

Outline the mechanism for the reaction between propanone and NaBH₄

3.3.8

3.3.8 & 3.3.7 (part)

1

Outline the mechanism for the reaction between propanal + KCN then acid

3.3.8

3.3.8 & 3.3.7 (part)

1

Which of the following is the correct general equation for the reaction between hydrogen cyanide and an aldehyde?

RCHO(aq) + KCN(aq) --> RCH(OH)CN(aq) + K+ (aq)

RCHO(aq) + HCN(aq) --> RCH(OH)CN(aq)

RCOR’(aq) + KCN(aq) --> RCH(OH)CN(aq) + K+ (aq)

RCOR’(aq) + HCN(aq) --> RCH(OH)CN(aq)

3.3.8

3.3.8 & 3.3.7 (part)

1

Which of the following statements, about working with potassium cyanide, is FALSE?

It is an irritant

It is dangerous if inhaled

It is harmless if ingested

A fume cupboard should be used

3.3.8

3.3.8 & 3.3.7 (part)

1

Outline the mechanism between acidified potassium cyanide and methanal

3.3.8

3.3.8 & 3.3.7 (part)

1

Draw both enantiomers for the reaction between KCN and Butanone

3.3.8

3.3.8 & 3.3.7 (part)

3.8 Aldehydes and Ketones

Propanone can be reduced to form an alcohol. A functional group isomer of the alcohol formed is

Which one of the following conversions does not represent a reduction?

CH2O is the empirical formula of

Which one of the following does not represent an oxidation?

Which one of the following reactions involves nucleophilic addition?

Which one of the following isomers is not oxidised under mild reaction conditions?

Which one of the following is not a suitable method for the preparation of ethanol?

How many structural isomers, which are aldehydes, have the molecular formula C5H10O?

Which one of the following will undergo nucleophilic addition?

Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

On reduction, a racemate can be formed by

Which one of the following statements about but-2-enal, CH3CH=CHCHO, is not true?

Which one of the following reactions will produce an organic compound that has optical isomers?

In which one of the following mixtures does a redox reaction occur?

Which one of the following would not reduce an acidified aqueous solution of potassium dichromate(VI)?

Which one of the following can act as an oxidising agent but not as a reducing agent?

Part a: Butanone is reduced in a two-step reaction using NaBH4 followed by dilute hydrochloric acid.Write an overall equation for the reduction of butanone using [H] to represent the reductant.

Part B: By considering the mechanism of the reaction, explain why the product has no effect on plane polarised light.

Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.Reagent:Conditions:Type of reaction:

Propanal is an isomer of propanone. Draw the structure of propanal

Draw the structural formula and name the organic product. If no reaction, write no reaction!propanal + NaBH4 -->

Draw the structural formula and name the organic product. If no reaction, write no reaction!propan-1-ol + H2SO4 / K2Cr2O7 distilling off the product

Draw the structural formula and name the organic product. If no reaction, write no reaction!butanal + Tollen’s reagent with heating

Draw the structural formula and name the organic product. If no reaction, write no reaction!butanone + NaBH4

Outline the mechanism for the reaction between propanone and NaBH4

Outline the mechanism for the reaction between propanal + KCN then acid

Which of the following is the correct general equation for the reaction between hydrogen cyanide and an aldehyde?

Which of the following statements, about working with potassium cyanide, is FALSE?

Outline the mechanism between acidified potassium cyanide and methanal

Draw both enantiomers for the reaction between KCN and Butanone

Propanone can be reduced to form an alcohol. A functional group isomer of the alcohol formed is

Which one of the following conversions does not represent a reduction?

CH2O is the empirical formula of

Which one of the following does not represent an oxidation?

Which one of the following reactions involves nucleophilic addition?

Which one of the following isomers is not oxidised under mild reaction conditions?

Which one of the following is not a suitable method for the preparation of ethanol?

How many structural isomers, which are aldehydes, have the molecular formula C5H10O?

Which one of the following will undergo nucleophilic addition?

Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

On reduction, a racemate can be formed by

Which one of the following statements about but-2-enal, CH3CH=CHCHO, is not true?

Which one of the following reactions will produce an organic compound that has optical isomers?

In which one of the following mixtures does a redox reaction occur?

Which one of the following would not reduce an acidified aqueous solution of potassium dichromate(VI)?

Which one of the following can act as an oxidising agent but not as a reducing agent?

Part a: Butanone is reduced in a two-step reaction using NaBH4 followed by dilute hydrochloric acid.Write an overall equation for the reduction of butanone using [H] to represent the reductant.

Part B: By considering the mechanism of the reaction, explain why the product has no effect on plane polarised light.

Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.Reagent:Conditions:Type of reaction:

Propanal is an isomer of propanone. Draw the structure of propanal

Draw the structural formula and name the organic product. If no reaction, write no reaction!propanal + NaBH4 -->

Draw the structural formula and name the organic product. If no reaction, write no reaction!propan-1-ol + H2SO4 / K2Cr2O7 distilling off the product

Draw the structural formula and name the organic product. If no reaction, write no reaction!butanal + Tollen’s reagent with heating

Draw the structural formula and name the organic product. If no reaction, write no reaction!butanone + NaBH4

Outline the mechanism for the reaction between propanone and NaBH4

Outline the mechanism for the reaction between propanal + KCN then acid

Which of the following is the correct general equation for the reaction between hydrogen cyanide and an aldehyde?

Which of the following statements, about working with potassium cyanide, is FALSE?

Outline the mechanism between acidified potassium cyanide and methanal

Draw both enantiomers for the reaction between KCN and Butanone

CH₂O is the empirical formula of

How many structural isomers, which are aldehydes, have the molecular formula C₅H₁₀O?

Which one of the following statements about but-2-enal, CH₃CH=CHCHO, is not true?

Part a: Butanone is reduced in a two-step reaction using NaBH₄followed by dilute hydrochloric acid.
Write an overall equation for the reduction of butanone using [H] to represent the reductant.

Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.
Reagent:
Conditions:
Type of reaction:

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propanal + NaBH₄ -->

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propan-1-ol + H₂SO₄ / K₂Cr₂O₇ distilling off the product

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanal + Tollen’s reagent with heating

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanone + NaBH₄

Outline the mechanism for the reaction between propanone and NaBH₄

CH₂O is the empirical formula of

How many structural isomers, which are aldehydes, have the molecular formula C₅H₁₀O?

Which one of the following statements about but-2-enal, CH₃CH=CHCHO, is not true?

Part a: Butanone is reduced in a two-step reaction using NaBH₄followed by dilute hydrochloric acid.
Write an overall equation for the reduction of butanone using [H] to represent the reductant.

Give a suitable reagent and state the necessary conditions for the conversion of propan-2-ol into propanone. Name the type of reaction.
Reagent:
Conditions:
Type of reaction:

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propanal + NaBH₄ -->

Draw the structural formula and name the organic product. If no reaction, write no reaction!
propan-1-ol + H₂SO₄ / K₂Cr₂O₇ distilling off the product

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanal + Tollen’s reagent with heating

Draw the structural formula and name the organic product. If no reaction, write no reaction!
butanone + NaBH₄

Outline the mechanism for the reaction between propanone and NaBH₄