Highlights
Module 2 scenario-based Problems
Fixing dis-functional organic chemical dataEster recently commenced work at the company “Functional Compounds”, a supplier of organic chemicals. She discovered a database had become corrupted, affecting some chemical names, structures, reaction descriptions and other data. Ester’s task is to sort out the chemical database. Listed below are some of the mistakes she noticed and must therefore correct.
The first task is to sort out compounds with the same molecular formula of C6H8 but different chemical properties. Only C6H8 compounds that incorporate 3, 4 or 5 membered rings and compounds incorporate triple bonds were retained in the database, e.g.
Ten structural isomers with the formula C6H8 were missing, only one of which has been identified as shown in the table on the next page.
Q1 (a). Draw line structures for 9 of the remaining possible structural (not geometric) isomers of C6H8 that do not have 3, 4 or 5 membered rings and do not have triple bonds. Next to each isomer, write their correct IUPAC names. Use a table laid out like the template on the next page.
(hint: double bonds will be required, and the set will include cumulenes that contain consecutive double bonds, i.e. C=C=C )
Ester realised that some of these compounds might have geometric isomers and that they should be identified.
(b) Draw and clearly label both Z and E isomers for ONE of the compounds from part (a) that has geometric isomers.
[Insert image(s) of your structure drawings here, use the following table as a guide to answer this question. Either print the table below or sketch it roughly with your answers]
Isomer number Structural Isomer of C6H8 IUPAC name
example 3-methylenepenta-1,4-diene or
3-methylene-1,4-pentadiene
1 2 3 4 5 6 7 8 9
Ester saw the following reaction diagram in which some of the reactions and chemical names were incorrectly labelled. The reactions were also missing data about reactants and products.
Q2. Complete the table below to provide the following information on each of the reactions shown:
• name the type of reaction, choosing from this list: Acid/Base, Addition, Combustion, Condensation, Elimination, Substitution.
• name the functional groups (such as alkane, alkene, aldehyde etc) that the product belongs to.
ANSWER: [Write your answers in the shaded cells of this table]
Reaction Reaction type Product (functional group)
Q3. State the relationship between each pair of structures specified below. e.g. Are they structural isomers, geometric isomers or neither? Give a brief explanation / justification in each case.
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