Hydrocarbon Derivatives These are organic compounds that are based on hydrocarbons with the addition of specific functional groups A functional group is a reactive group of atoms (eg. –OH)
Due to the reactivity of the functional groups, we can determine the physical and chemical properties of compounds We also classify compounds based on these groups We will now explore six groups of hydrocarbon derivatives
Alcohols An organic compound containing the hydroxyl, –OH, functional group Have the general formula of R—OH The “R” represents the alkyl group Example: CH 3 —CH 2 —OH
Naming Rules 1.Locate the longest carbon chain (must contain the carbon attached to the –OH group.) Name the parent alkane 2.The suffix is –ol; indicate the position of the –OH group in front of the suffix 3.More than one –OH group; use di, tri, tetra and keep entire root name 4.Number the chain so that the –OH group has the lowest number 5.Add a position number before the name of the root to indicate the position of the –OH group 6.Name and number any branches (as you would for alkanes) 7.Put it all together:branches + root
One more... Name this alcohol and state whether it is primary, secondary or tertiary. CH 3 —CH—CH 2 —CH 2 —CH 3 | OH
Draw: 3,4-dimethylhexan-2-ol Butane-1,3-diol
Three classes of Alcohols Primary Alcohol (1°) – the OH group is bonded to a carbon that is only bonded to one other carbon Secondary Alcohol (2°)– the OH group is bonded to a carbon that is bonded to two other carbon atoms Tertiary Alcohol (3°)– the OH group is bonded to a carbon that is bonded to three other carbon atoms
Physical properties of alcohols Polar or non-polar? Boiling points? Intermolecular forces?
Haloalkanes HCs with at least one halogen atom Basic structure R-X, where R is the root and X can be F, Cl, Br, I Often result of substitution reactions Eg. Chloroform, CFCs (refrigerants & propellants)
Naming haloalkanes 1.Identify the root – longest continuous chain 2.Identify the suffix – which family 3.Type of halogen (F-fluoro, Cl-chloro, Br-bromo, I-iodo); more than one – di, tri, etc 4.Halogen gets the lowest number 5.Then look for alkyl groups 6..Halogen substituent groups and alkyl side groups are arranged alphabetically
Physical properties polarity/solubility in water? Boiling points?
Aldehyde Contain a formyl group, which is a carbonyl functional group >C=O with a H bonded to the C atom Only one possible position – always C#1 Have characteristic scents and tastes Example – Cinnamon or Formaldehyde, vanillin, cilantro
Naming Aldehydes As with other naming (ID root) The carbonyl group will always be on a terminal carbon, thus there is no need to give a position number Simply name the carbon chain; drop the –e from the end and add –al; give the C=O position 1 Add branches (if any) as you have for all others!
Try Some HC—CH 2 —CH 2 —CH 3 CH 3 —CH 2 —CH—CH Try page 52: # O || O | CH 2 —CH 3
Physical properties of aldehydes Polarity? Boiling points? Compared to alcohols?
Ketones Contain the carbonyl group C=O Has an alkyl group on either side of the C=O General formula R-CO-R`
Naming Ketones Find the longest carbon chain containing C=O Number the chain so that C=O has lowest number Drop the final –e from the alkane name and add –one Name and add branches as you would for alkanes
Try These CH 3 —CH 2 —CH 2 —C—CH 3 CH 3 —CH—C—CH 2 —CH 2 —CH 3 | CH 3 O || O
Carboxylic Acids Contain a carboxyl group —C—OH General formula of R—COOH Polar molecules Soluble in water Have high MP and BP O ||
Naming Carboxylic Acids Name the parent alkane; drop the –e at the end of the alkane name and add –oic acid Carboxyl group is always given position one (no need to state this!) Name any branches as we do for alkanes
Try some CH 3 —C—OH CH 3 —CH—CH 2 —C—OH | CH 3 O || O
Esters Derivatives of carboxylic acids Contains the functional group —C—O— General formula RCOOR` Example: CH 3 —CH 2 —C—O—CH 3 O || O
Naming Esters Choose the main part of the ester, containing the C=O group. Name this as the parent acid. Replace the –oic acid with –oate Name the second part of the ester as an alkyl group Put them together – alkyl group + parent acid
CH 3 —CH 2 —C—O—CH 3 We would name thismethyl propanoate O || Parent acid Alkyl Group
Try One CH 3 —CH 2 —CH 2 —CH 2 —C—O—CH 2 —CH 3 O ||
Ethers An organic compound that has two alkyl groups joined by an oxygen atom Has the general formula of R—O—R` R and R` indicate two alkyl groups The can be the same or different Example: CH 3 —CH 2 —O—CH 3
How do we get to this? You can think of alcohols and ethers as derivatives of water! H—O—H Water R—O—H Alcohol R—O—R`Ether
Rules for naming Common Names 1.List the alkyl groups that are attached to the oxygen atom, in order of increasing length. 2.Place the suffix –ether at the end of the name No numbers are needed to show the location of the oxygen atom!