Hydrocarbon Derivatives Chemistry 11

Hydrocarbon Derivatives Are formed when one or more hydrogen atoms is replaced by an element or a group of elements other than hydrogen. Are formed when one or more hydrogen atoms is replaced by an element or a group of elements other than hydrogen. Halogens (F 2, Cl 2, Br 2, I 2,) can all add to a hydrocarbon to form an alkyl halide. Halogens (F 2, Cl 2, Br 2, I 2,) can all add to a hydrocarbon to form an alkyl halide. The atom or group of atoms that are added to the hydrocarbon are called functional groups. The atom or group of atoms that are added to the hydrocarbon are called functional groups.

Functional Group Is the reactive part of the organic molecules Is the reactive part of the organic molecules Each functional group behaves and reacts in a particular way. Each functional group behaves and reacts in a particular way.  they help us determine the physical and chemical properties of compounds.  they help us determine the physical and chemical properties of compounds.

Alcohol Has a hydrogen replaced by a hydroxyl Has a hydrogen replaced by a hydroxyl (-OH) group. Have the general formula of R—OH Have the general formula of R—OH The “R” represents the alkyl group The “R” represents the alkyl group Example : CH 3 —CH 2 —OH The name of the hydrocarbon that was substituted determines the name of the alcohol. The name of the hydrocarbon that was substituted determines the name of the alcohol.

Rules for Naming Alcohols The alcohol is named using the hydrocarbon name and adding the suffix –ol. The alcohol is named using the hydrocarbon name and adding the suffix –ol. If methane is substituted with an OH group it becomes methanol. If methane is substituted with an OH group it becomes methanol. If a pentane group is substituted with an OH group it is pentanol. If a pentane group is substituted with an OH group it is pentanol. Assign lowest possible values to the -OH Assign lowest possible values to the -OH

3 Classes of Alcohols Primary Alcohol (1°) – the OH group is bonded to a carbon that is only bonded to one other carbon 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 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 Tertiary Alcohol (3°) – the OH group is bonded to a carbon that is bonded to three other carbon atoms

Name these alcohols and identify them as primary, secondary, or tertiary.

Draw condensed structural formulae for the following: (a) methanol (b) 3-ethyl-4-methyl-1-octanol (c) 2-propanol (d) 2,4-dimethyl-1-cyclopentanol (e) 2,2-butanediol

Homework: Page 363 → #4, 6, 7, 9 Page 363 → #4, 6, 7, 9 Page 388 → #10 Page 388 → #10 Page 391 → #12, 13 Page 391 → #12, 13

Aldehydes Contain a carbonyl functional group C=O Contain a carbonyl functional group C=O Has the general formula R-CHO Has the general formula R-CHO Have characteristic scents and tastes Have characteristic scents and tastes Example : Example : Formaldehyde Formaldehyde

Rules for Naming Aldehydes 1.The carbonyl group will always be on a terminal carbon, thus there is no need to give a position number 2.Simply name the carbon chain 3.Drop the –e from the end and add –al 4.Give the C=O position 1 5.Add/name branches as you have for all others!

Try These: HC—CH 2 —CH 2 —CH 3 CH 3 —CH 2 —CH—CH CH 3 —CH 2 —CH—CH O || O | CH 2 —CH 3

Ketones Contain the carbonyl group C=O Contain the carbonyl group C=O Has an alkyl group on either side of the C=O Has an alkyl group on either side of the C=O General formula: General formula:

Rules for Naming Ketones 1.Find the longest carbon chain containing C=O 2.Number the chain so that C=O has lowest number 3.Drop the final –e from the alkane name and add –one 4.Name and add branches as previously.

Name These: CH 3 —CH 2 —CH 2 —C—CH 3 CH 3 —CH 2 —CH 2 —C—CH 3 CH 3 —CH—C—CH 2 —CH 2 —CH 3 CH 3 —CH—C—CH 2 —CH 2 —CH 3 | CH 3 CH 3 O || O

Name These:

Draw a condensed structural diagram for each aldehyde or ketone. (a) 2-propylpentanal (b) cyclohexanone (c) 4-ethyl-3,5-dimethyloctanal

Question: Is a compound with a C=O bond and the molecular formula C 2 H 4 O an aldehyde or a ketone ? Explain. Solution This compound must be an aldehyde. There are only two carbon atoms, so it is not possible for the carbonyl group to have an alkyl group on each side.

Draw (line diagrams) and name 5 ketones and aldehydes with the molecular formula C 6 H 12 O (isomers)

Ethers An organic compound that has two alkyl groups joined by an oxygen atom An organic compound that has two alkyl groups joined by an oxygen atom Has the general formula of R—O—R` Has the general formula of R—O—R` R and R` indicate two alkyl groups R and R` indicate two alkyl groups The can be the same or different The can be the same or different Example : CH 3 —CH 2 —O—CH 3

Rules for Naming Ethers 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 NOTE : No numbers are needed to show the location of the oxygen atom!

Name These: 1.CH 3 —CH 2 —O—CH 2 —CH 2 —CH 3 2.CH 3 —CH 2 —CH 2 —CH 2 —O—CH 2 —CH 3

Name These:

Carboxylic Acids Contain a carboxyl group Contain a carboxyl group—C—OH General formula of R—COOH General formula of R—COOH O ||

Rules for Naming Carboxylic Acids 1.Name the parent alkane 2.Drop the –e at the end of the alkane name and add –oic acid 3.Carboxyl group is always given position one (  no need to state this) 4.Name any branches as you have been previously doing.

Name These: CH 3 —C—OH CH 3 —CH—CH 2 —C—OH | CH 3 CH 3 O || O

Name These:

Name This:

Draw a condensed structural diagram for each carboxylic acid. (a) hexanoic acid (b) 3-propyloctanoic acid (c) 3,4-diethyl-2,3,5-trimethylheptanoic acid

Draw and name 2 carboxylic acids with the molecular formula C 4 H 8 O 2 (isomers)

Esters Derivatives of carboxylic acids Derivatives of carboxylic acids Contains the functional group: —C—O— Contains the functional group: —C—O— General formula RCOOR ` General formula RCOOR ` Example : CH 3 —CH 2 —C—O—CH 3 O || O

Rules for Naming Esters 1.Choose the main part of the ester, containing the C=O group. Name this as the parent acid. 2.Replace the –oic acid with –oate 3.Name the second part of the ester as an alkyl group 4.Put them together: alkyl group + parent acid

Example CH 3 —CH 2 —C—O—CH 3  We would name this methyl propanoate O || Parent Acid Alkyl Group

Name These:

Name This:

Question: For each ester in the previous question, name the carboxylic acid and the alcohol that are needed to synthesize it.

Draw line diagrams for each ester and write the molecular formula. (a) methyl pentanoate (b) heptyl methanoate (c) butyl ethanoate (d) propyl octanoate (e) ethyl 3,3-dimethylbutanoate

Draw and name 3 ester isomers with the molecular formula C 5 H 10 O 2