Organic Chemistry 1 · Naming organic compounds
Naming cycloalkanes and bicyclic compounds: practice problems
24 problems, each with its worked solution. Open one to read every step, or filter by tag.
Classify 9
- Name a methylated bridged C7 bicycleName a substituted bicyclo[x.y.z]alkane, numbering from a bridgehead along the longest bridge.
- Name a symmetric bridged C8 bicycleName a bicycloalkane from the carbon count of its three bridges.
- Name a three-membered ring with two wedged halogensUse cis to name two ring substituents on the same face.
- Name a cyclopentane with ethyl and methyl groupsName a disubstituted cyclopentane by lowest locants, then alphabetical order for C1.
- Name a cyclohexane with a methyl and a C3 branchName a disubstituted cyclohexane using the preferred prefix propan-2-yl and alphabetical order to choose C1.
- Name a four-membered ring carrying a five-carbon chainChoose the ring as the parent hydride over an attached chain, as the 2013 rules require.
- Name a methylated spiro compound of a five and a six ringName a substituted spiro[x.y]alkane, numbering the smaller ring first.
- Name a 1,4-disubstituted cyclohexane with wedgesName the relative configuration of two ring substituents with cis or trans.
- Name a cyclohexane with three methyl groupsFind the lowest locant set at the first point of difference for a trisubstituted ring.
Compare 2
- Rank bicyclic and spiro names by carbon countDecode bicyclo and spiro names into total carbon counts.
- Rank four cycloalkanes by ring strainRank cycloalkanes named by IUPAC names by total ring strain from angle and torsional strain.
Calculate 3
- Count the carbons in bicyclo[3.2.2]nonaneConvert a bicyclo descriptor into a carbon count.
- Count the stereoisomers of 1,2-dimethylcyclohexaneCount stereoisomers of a disubstituted ring, recognizing a meso cis isomer.
- Strain energy of cyclopropane from its heat of combustionCalculate ring strain from a heat of combustion and the strain-free value per CH2 group.
Find the error 4
- Diagnose the bracket order in a bridged C7 nameCite bicyclo bridge counts in decreasing order.
- Diagnose prefix order on a 1,4-disubstituted ringApply alphabetical order to both citation and C1 choice when ring locant sets tie.
- Diagnose a superfluous locant on a monosubstituted ringRecognize that a single substituent on a cycloalkane takes no locant.
- Diagnose a chain-parent name for a ring with a C5 branchApply the 2013 rule that a ring is senior to an acyclic chain as the parent hydride.
Interpret the evidence 4
- Pick the C8 bicycle with bridges of three, two and oneMatch bracket numbers in a bicyclo name to the bridge lengths of a drawing.
- Pick the structure for a cis-1,3-disubstituted cyclohexaneRecognize cis relative configuration and 1,3 placement on a cyclohexane drawing.
- Pick the gem-dimethyl bridged bicycle from its nameDecode a bicyclo name: find C7, the one-carbon bridge, and place two methyls on it.
- Pick the cyclohexane with a straight three-carbon chainDecode a ring-parent name with an unbranched alkyl prefix.
Explain why 2
- Why some cycloalkane names need cis or transExplain when a cycloalkane name must specify relative configuration.
- Why one ring substituent needs no locantExplain when ring locants are omitted and when every substituent needs one.
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