Synthesis

Beginning with an alkene shown in the gallery of possible starting materials, suggest a synthesis for each of the compounds shown on the left. Starting materials may be used more than once, or not at all.
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click on the target compound to review methods of synthesis;

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The target molecule is an alkane. Alkenes can be converted into alkanes by simple catalytic hydrogenation.

The target molecule is an alkyl bromide and the bromine is bonded to a secondary center which is adjacent to a tertiary center (an anti-Markovnikov addition). Alkenes can be converted into anti-Markovnikov alkyl bromides by addition of HBr in the presence of peroxides (radical addition, in which the bromine radical adds to form the most stable carbon radical).

The target molecule is an alcohol where the oxygen is bonded to a secondary center and there are no other carbons in the molecule which would form more stable carbocations (Markovnikov addition) . Alkenes can be converted into Markovnikov alcohols by acid-catalyzed addition of water (an ionic reaction involving a carbocation intermediate) or by oxymercuration, which gives Markovnikov regiochemistry without the potential for rearrangement.

The target molecule is an alkyl halide in which the bromine is bonded to a tertiary center and there are no other carbons in the molecule which would form more stable carbocations (Markovnikov addition) . Alkenes can be converted into Markovnikov alkyl bromides by direct addition of HBr (an ionic reaction involving a carbocation intermediate and the potential for rearrangement).

The target molecule contains an aldehyde and a ketone. Alkenes can be converted into aldehydes and ketones by ozonolysis, followed by dissolving metal reduction of the intermediate ozonide. In this reaction, the bicyclic alkene is split, as indicated, to produce both carbonyl groups in the same product molecule.

The target molecule is an alkyl halide and the bromine is bonded to a secondary center which is adjacent to a tertiary center which would form a more stable carbocation (anti-Markovnikov addition). Alkenes can be converted into anti-Markovnikov alkyl bromides by addition of HBr in the presence of peroxides (radical addition, in which the bromine radical adds to form the most stable carbon radical).

The target molecule is an alkane. Alkenes can be converted into alkanes by simple catalytic hydrogenation.

The target molecule contains an aldehyde and a ketone. Alkenes can be converted into aldehydes and ketones by ozonolysis, followed by dissolving metal reduction of the intermediate ozonide. Look for a single molecule in the starting materials which can form this product directly.