EasyChemistryHigh School (11–12)Organic Compounds with Functional Groups › Aldehydes, Ketones and Carboxylic AcidsConceptual
Name the reagent or reagents for each conversion, and name the reaction where it has a name…
Contributed by StemPy LabTry it on paper first. A hint, the key idea and the worked solution are here when you need them.
Name the reagent or reagents for each conversion, and name the reaction where it has a name.
- propanoyl chloride to propanal
- ethanenitrile to ethanal
- methyl ethanoate to ethanal
- propan-2-ol to propanone
- ethyne to ethanal
Need a reminder? The key ideaShow
A primary alcohol gives an aldehyde with PCC, or with copper at 573 K. A secondary alcohol gives a ketone. Terminal alkynes give methyl ketones with Hg and dilute acid. Rosenmund: acyl chloride, H, Pd-BaSO. Stephen: nitrile, SnCl and HCl, then water. The percentage yield is .
The worked solution
Have you tried it?
Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Step 1. An acyl chloride to an aldehyde: hydrogen over palladium on barium sulphate. This is the Rosenmund reduction.
Step 2. A nitrile to an aldehyde: tin(II) chloride and hydrochloric acid, then boiling water. This is the Stephen reduction. DIBAL-H and water also works.
Step 3. An ester to an aldehyde: DIBAL-H in a cold solvent, then water.
Step 4. A secondary alcohol to a ketone: acidified potassium dichromate, or any other oxidising agent.
Step 5. Ethyne to ethanal: water with mercury(II) sulphate and dilute sulphuric acid at .
Check. Only the last two reactions are not reductions.
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