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Fundamentals of Organic Chemistry Topic 10.1 • functional groups are the reactive part of molecules • they determine the class of chemical being referred to • see hand out giving: – class – functional group – suffix – general formula - example The following three slides are really not necessary anymore. See the hand out given in class Compounds up to 6 carbon atoms with functional groups Functional Group Alcohol Formula -OH Aldehyde -COH (on the end Structural Formula -O–H O of a chain) -C–H Ketone -CO- (can’t be on O end of chain) -C– Carboxylic Acid -COOH (on the O end of a chain) -C–O–H Halide -Br, -Cl, -F, -I -X Compounds up to 6 carbon atoms with functional groups Functional Group Formula Alcohol -OH Suffix (or Prefix) -ol Aldehyde -COH -al Ketone -CO- -one Carboxylic Acid -COOH -oic acid Halide -Br, -Cl, -F, -I bromo-,chloro-, fluoro-,iodo- Alcohols: suffix = “-ol” propan-1-ol propan-2-ol 2-methyl propan-2-ol Aldehydes: suffix = “-al” propanal Note: an aldeyhde group is always on an end carbon so don’t need a number butandianal Ketones: suffix = “-one” propanone (don’t need C# with only three carbons) butanone (don’t need C#, only four carbons) penta-2-one butandione pentan-3-one Butan-2-one Carboxylic Acids: suffix = “-oic acid” butanoic acid Note: a carboxyl is always on an end carbon propandioic acid Halogenalkanes: prefixes = “fluoro, chloro, bromo, iodo” 1-bromopropane 2-chlorobutane 1,2-diiodoethane 1,2-difluoroethene 1,2-difluoroethene 1,1,2-trifluoroethene Esters: suffix = “-oate” • two chains interrupted by an oxygen • one chain is based on the chain containing the single bonded O • this chain come first in the name • the other chain is based on the chain including the carbonyl group. • this chain has the ending “oate” on it Ethers: You should know ethers for IB but I’m not going to test you on it. http://www.chem.ucalgary.ca/cou rses/351/orgnom/ethers/ethers01.html Identify primary, secondary and tertiary carbon atoms in alcohols (-OH) and halogenoalkanes (-F, -Cl, -Br, -I) • with reference to the carbon that is directly bonded to a hydroxyl or a halogen – Primary = carbon atom is only bonded to one other carbon – Secondary = carbon atom is bonded to two other carbons – Tertiary = carbon atom is bonded to three other carbons Aromatic hydrocarbons • contain a benzene ring • the name of the class come from the fact that many of them have strong, pungent aromas • an unsaturated carbon where the double bonds resonate back and forth with the single bonds • physical evidence for its structure – benzene crystallizes when cooled • analysis of this showed that all six C-C bonds had identical lengths (140 pm) – this allows the molecule to be symmetrical instead of the different lengths associated with singe (154 pm) and double (134 pm) • chemical evidence for its structure – does not react as other unsaturated carbons do when adding hydrogen (hydrogenation) to them • Richard Thornley 10.1 (start at 3:20) • I don’t think the following slides are in Topic 10 anymore. However, they should look familiar from Topic 4 since it is still relevant to the class. Discuss the volatility and solubility in water of compounds • Volatility: how easily a substance turns into a gas – the stronger the intermolecular force, the less volatile it is – ionic › hydrogen bonding › dipole-dipole › van der Wall’s – therefore volatility from highest to lowest… – alkane (only Van der Wall’s) › halogenoalkane › aldehyde › ketone › amine › alcohol (H bonding) › carboxylic acid (H bonding) Boiling Points • Solubility: a solute’s ability to dissolve in a polar solvent (water) – the more polar a substance is, the more soluble it is – solubility decreases as chain length increases – smaller alcohols, aldehydes, ketones & carboxylic acids are typically soluble • they are all polar as is water