Stereoisomerism questions

Assignment: Questions on Topic 20.3: Stereoisomerism

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Deduce how many different four-membered ring isomers exist for dichlorocyclobutane and name each isomer.

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i. Explain why 1,2-dichloroethane cannot exhibit cis/trans isomerism whereas 1,2-dichloroethene can.

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II. Explain whether or not 1,2-dichloroethane can show conformational isomerism.

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Explain why cis-butenedioic acid reacts to form a cyclic compound with the loss of water when heated whereas trans-butenedioic acid does not.

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2-amino acids have the general formula H2NCH(R)COOH. Explain why glycine, H2NCH2COOH, the simplest 2-amino acid, does not exist in two enantiomeric forms whereas all the other 2-amino acids do.

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Three of the first four compounds shown in Section 37 of the IB Chemistry data booklet are the ‘over the counter’ pain killers, aspirin, paracetamol (acetaminophen) and ibuprofen.

i. Identify which, if any, can show optical isomerism.

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ii. The fourth is penicillin. Explain whether this also be optically active?

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The straight chain structural formula of glucose is given in Section 34 of the IB Chemistry data booklet. Explain why glucose can have diastereomers.

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Name the following compounds, A and B, using E/Z nomenclature.

A 

 

B 

 

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