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5 cards from this section. Quick, good the night before a test.
What is the difference between the structures of ethanenitrile and methyl isocyanide?
Look at which atom of the CN group is attached to CH3.
Give the IUPAC names of C2H5CN and C2H5NC.
Count the CN carbon in a nitrile name but not in an isocyanide name.
The carbon atom of the –C≡N group in a nitrile is:
A triple bond leaves two orbitals for σ bonds.
The IUPAC name of CH3CH2CH2CN is:
Count the carbon of the CN group too.
Two isomers X and Y have the formula C3H5N. X is made from bromoethane and KCN, and Y from bromoethane and AgCN. (a) Identify X and Y. (b) Predict the products of their reduction with sodium and ethanol. (c) Which of them would you expect to have an extremely unpleasant smell, and where is this property used?
The atom attached to the ethyl group stays attached after reduction.
Methyl isocyanide changes into ethanenitrile on heating. (a) Show that the two have the same molecular formula. (b) Using bond types and formal charges, suggest why the nitrile is the more stable isomer.
Compare the formal charges, and the bond that holds the methyl group in each isomer.
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