Carbonyl Compounds (OCR A Level Chemistry)

NaBH₄ is a common reducing agent used in Organic Chemistry.

Identify the organic compound that would undergo reduction, using NaBH₄, to produce butan-2-ol.

Propanone can also be converted into a secondary alcohol.

Name and outline the mechanism for this reaction.

Explain why the secondary alcohol produced in part (b) demonstrates no optical activity.

A racemic mixture was formed from the reaction of the aldehyde pentanal with KCN, followed by dilute acid.

Draw the displayed formulae of the organic products responsible for the racemic mixture.

Propanal can be converted into 2-hydroxybutanoic acid by a two-step synthesis as outlined in Figure. 

Hydrogen cyanide is a weak acid that can be used to extend the length of  a carbon chain in a controlled fashion. Potassium cyanide is often used as an alternative
due to the well documented poisonous effects of hydrogen cyanide. 

Use your knowledge of rates of reaction to explain another reason why potassium cyanide would be the preferred reagent to perform Step 1.

In Step 1 of the reaction sequence shown in part (a), propanal is converted into an intermediate.

The products formed when propanal reacts with KCN exhibit optical isomerism.

Draw 3 dimensional structures of these stereoisomers.

An isomer of propanal undergoes the Step 1 reaction as outlined in Figure 1 from part (a),  but the product of this reaction has no effect on plane polarised light.

Draw the product and explain why there is no effect on plane polarised light.

Compound W can be converted into three different organic compounds as shown by the reaction scheme in Figure 1.

Figure 1

Write an equation for the formation of X. Use [H] to represent the reagent in the equation.

Identify the specific type of isomerism shown by the product Y, in Figure 1. 

Outline the mechanism to show the formation Y and explain how this leads to the isomers of Y. 

When 5.00 cm³ of propanal (Mr = 58.0) were reacted with an excess of acidified potassium dichromate (VI) solution, 4.25 g of propanoic acid (Mr = 74.0) were obtained.

The density of propanal is 0.810 g cm⁻³. 

Calculate the percentage yield for this reaction.

In another experiment, a student made propanoic acid from propanal, however they did not see the orange to green colour change that they were expecting.

The student did not see the initial colour of the mixture but at the end of their experiment they described their reaction mixture as a dull and murky orange colour.

After testing propanal, propanone and propan-1-ol with acidified potassium dichromate(VI) solution, a second set of test-tube reactions was performed. 

Suggest how the organic compounds, propanal, propanone and propan-1-ol were further identified using Tollens’ reagent. 

In separate test tubes, 2,4-dinitrophenylhydrazine was used to test the organic compounds, propanal, propanone and propan-1-ol. When 2,4-dinitrophenylhydrazine is added to an organic compound, the observation if a carbonyl group is present is a yellow-orange precipitate. 

Explain why 2,4-dinitrophenylhydrazine does not confirm the presence of propanal and suggest an alternative test tube reaction, that has not been performed yet, to prove that one of the organic compounds is propanal.

Acidified potassium dichromate (VI) solution is less expensive than Tollen’s reagent.
Suggest why Tollens’ reagent is still used as the oxidising agent in the specific test for aldehydes.

Three compounds, X, Y and Z, were found to be structural isomers with a relative molecular mass of 72.

Analysis shows them to contain the following percentages by mass: 

C - 66.7% H - 11.1% O - 22.2% 

Calculate the molecular formula of the isomers.

All three isomers, X, Y and Z, show a sharp IR absorption peak at around 1750 cm^-1. 

Use this information and your answer to part (a) to suggest possible structural formulae for the isomers, X, Y and Z.

Certain reagents can be used to oxidise two of the three isomers, X, Y and Z.

Spectroscopic methods are commonly used to identify chemicals.

Aqueous sodium tetrahydridoborate, NaBH₄, is a common reducing agent.

Identify two isomers with the formula C₃H₆O that cannot be reduced by aqueous NaBH₄.

Identify the two isomers with the formula C₃H₆O that can be reduced by aqueous NaBH₄.

When NaBH₄ is used as a reducing agent followed by the addition of acid, the reduction products of ketones can exhibit optical isomerism, while the reduction products of aldehydes cannot.

Explain why the reduction product of a carbonyl compound, by NaBH₄ and acid, cannot be a tertiary alcohol.

This question is about the boiling points of organic compounds.

The boiling points of three organic compounds are shown in Table 1.

Table 1

Suggest a value for the boiling point of propanone. Justify your answer.

Explain why there are no hydrogen bonds between propanone molecules, even though propanone forms hydrogen bonds in water.

Describe one test tube reaction that could be used to distinguish between samples of propanal and propanone.

This question is about an unknown organic compound A.

An organic compound, A, has the molecular formula C₅H₈O and undergoes nucleophilic addition with sodium tetrahydridoborate. 

Identify the nucleophile in this reaction.

As shown, the organic compound, A, reacts with sodium tetrahydridoborate, NaBH₄, to form a symmetrical, secondary alcohol, B, as shown.

A + 2[H] → B

Identify the organic compounds A and B. Justify your answer.

Suggest one chemical test, including the expected result, that helps to prove your structure of compound B in part (b).

Outline the mechanism for the formation of compound B.

This question is about the reactions of an organic compound R.

Analysis of 15.0 g of an organic compound, R, showed it to contain 69.8% carbon, 2.79 g of oxygen and the remaining mass was hydrogen.

Compound R is a straight chain organic compound. One isomer of compound R produces optical isomers of compound S when reacted with potassium cyanide
followed by dilute acid.

Compounds R and S were tested with acidified potassium dichromate(VI) and Tollens reagent. The results are shown in Table 1.

Table 1

Using this information and your answer from part (a), identify compounds R and S.
Justify your answer.

Draw 3D representations of the two optical isomers of compound S.

There are some isomers of compound S that do not display optical isomerism.

Draw the skeletal formula of these isomers.