CNGNGE JOHN MCMURRY CHAPTER 4 Organic Compounds: Cycloalkanes and Their Stereochemistry IH1 RD EDIION Organic Chemistry with Biological Applications
CHAPTER 4 Organic Compounds: Cycloalkanes and Their Stereochemistry
Cyclics Most organic compounds contain rings of carbon atoms Chrysanthemic acid H3C CH3 Occurs naturally as esters -Active insecticidal Chrysanthemic acid -H constituents of chrysanthemum CO>H flowers Prostaglandins CO2H Potent hormones Prostaglandin E1 CH3 Control physiological functions HO in humans HO CH2OH Steroids CH3 0 Contain four joined rings OH Naturally occurring hormones CH3 Cortisone in plants and animals H
Most organic compounds contain rings of carbon atoms Cyclics Chrysanthemic acid ▪ Occurs naturally as esters ▪ Active insecticidal constituents of chrysanthemum flowers Prostaglandins ▪ Potent hormones ▪ Control physiological functions in humans Steroids ▪ Contain four joined rings ▪ Naturally occurring hormones in plants and animals
4-1 Naming Cycloalkanes Cycloalkanes or Alicyclic Compounds_(aliphatic cyclic) Saturated cyclic hydrocarbons containing rings of carbon atoms (CH2)n or CnH2n Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cengago Leaming.All Rights Rasorvod
Cycloalkanes or Alicyclic Compounds (aliphatic cyclic) ▪ Saturated cyclic hydrocarbons containing rings of carbon atoms ▪ (CH2 )n or CnH2n 4-1 Naming Cycloalkanes
Naming Cycloalkanes Step 1-Find the parent by counting carbon atoms Named as alkyl-substituted cycloalkane The number of carbon atoms in the ring is equal to or greater than the number in the substituent Named as cycloalkyl-substituted alkane The number of carbon atoms in the largest substituent is greater than the number in the ring CH3 CH2CH2CH2CH3 3 carbons 4 carbons Methylcyclopentane 1-Cyclopropylbutane
Named as alkyl-substituted cycloalkane ▪ The number of carbon atoms in the ring is equal to or greater than the number in the substituent Named as cycloalkyl-substituted alkane ▪ The number of carbon atoms in the largest substituent is greater than the number in the ring Step 1 – Find the parent by counting carbon atoms Naming Cycloalkanes
Naming Cycloalkanes Step 2-Number the substituents,and write the name Choose attachment point as carbon 1 and number carbon atoms on the ring so that second substitutent has lowest number possible. CH3 CH3 6 2 6 3 NOT 5 5 3 4 CH3 CH3 1,3-Dimethylcyclohexane 1,5-Dimethylcyclohexane Lower Higher Cengg Leaming All Pits Paserved
▪ Choose attachment point as carbon 1 and number carbon atoms on the ring so that second substitutent has lowest number possible. Step 2 – Number the substituents, and write the name Naming Cycloalkanes