4.5 Naming Cycloalkanes Cyctoatkanes are named by using similar rules. but the prefix eyclo- Immediately precedes the name of the parent. Ang a prescnt prefix) + cycle + What and where What i the functional group? are tre substituents? 41. Find the parent eyeloalkane. Hs 6 C’s in the ring ——> cyclohexane cots2. Name and number the substituents. No mumber is needed to indicate the location of a single substituent. CHa Ore O-f. CHa methyicyclohexane tert-butyicyclopentane For rings with more than one substituent, begin numbering at one substituent and proceed around the ring to give the second substituent the lowest number. numbering clockwise numbering counterclockwise CHs a a4 GHy CH groups at G1 and ©3 CH groups at C1 and 65 The 2m substituent has @ lower number. Correct: 1,3-dimethyleyclahexane. Incorrect: + 5-dimethylcyclohexaneWith two different substituents, number the ring to assign the lower number to the substituents alphabetically. Begin numbering at the ethyl group. Begin numbering at the methyl group. CH,CH, CHACH, fe 2 543 CH, CHs + ethyl group at C1 + methy| group at C1 + methyl group at C3 * ethyl group at C3 | earlier letter —-lower number | Correct: 1-cthy|-3-methylcyclohexane Incorrect: 3-ethyl-1-mathyloyclohaxane Note the special case of an alkane composed of both a ring anda long chain. If the number of carbons in the ring is greater than or equal to the number of carbons in the longest chain, the compound is named as a cycloalkane.Figure 4.2 ‘Two contrasting examples—Naming compounds containing both a ring and a long chain of carbon atoms: more carbons in the ring more carbons in the chain 4C's in the chain — 6 C's iin the chain — a butyl group ahexane | | | | 6 C's in the ring—cyclohexane 4C’'s in the ring—a cyclobutyl croup | Name as a cyclohexane with a substituent | | Name as a hexane with a substituent. Answer: butylcyclohexane Answer: 1-cyclobutylhexaneFigure 4.3 Examples of cycioatkane nomenclature CHCHy |“ ethyleyelobutane | 1-sec-buty!-3-methyleyclohexane [sneer eee needed ] | Assign the lower number to the 1* substituent | w ith only one substituent. |_| alphabeticaly: the b of butyl before the m of methyl. CHy CH,CHs CH, 'CHCH; 1,2,4-triethyleyclopentane 1,2-dimethyleyclohexane | Number to give the 2" CH group Number to give the 2" CHyCHz group the] the lower number: 1,.2- not 1.6-. lower number: 1,2,4- not 1,3,4- oF 1,3,5-.4.7 Fossil Fuels: Barrel of crude oil renuyiiab anes ices petroloum feadstocks 1.25 gat te oe eee ae (chemical products, plastics) natural gas and petroleum. asphalt and road oil 1.3 gal Natural gas is com- boiler oil 2.9 gal posed largely of other 4.2 gal methane, with lesser (lubricants, waxes, solvents) amounts of ethane, jet fuel 4.2 gal propane and butane. diesel and home heating oi| 8.4 gal gasoline 19.7 gal Petroleum is a complex mixture of compounds, most of which are hydrocarbons containing one to forty carbon atoms. Distilling crude petroleum (called refining), separates it into usable fractions that differ in boiling point. gasoline: C5H,,—C,,H2, Kerosene: C,,Hj.-—CgHae diesel fuel: C,sHy—CigHog a2Figure 4.5 Refining crude petroleum into usable fuel and other petroleum products. (a) An oil refinery. At an oil refinery, crude petroleum is separated into fractions of similar boiling point by the process of distillation. (b) Schematic of a refinery tower. As crude petroleum is heated, the lower- boiling, more volatile components distill first, followed by fractions of progressively higher boiling point. ‘J ©) Gases (Boling point range batow 20°C Gasaline 20-200 °C Kerosene 1TS-275°C Fuel ot ‘250-400 °C ‘Cruee ait and vapor are praheatod Lubricating alt above 350 °C Residue (asphalt)