Presentation on theme: "Alkyl Halides Organic compounds containing at least one carbon-halogen bond (C-X) X = F, Cl, Br, or I X replaces an H Properties and some uses Fire-resistant."— Presentation transcript:
1Chapter 8 Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides
2Alkyl HalidesOrganic compounds containing at least one carbon-halogen bond (C-X)X = F, Cl, Br, or IX replaces an HProperties and some usesFire-resistant solventsRefrigerantsPharmaceuticals and precursors
4Common Naming Rules Generally used only for simple compounds Identify the alkyl group and name it as a substituentchange the ending from “-ane” to “-yl,” if applicableIdentify the halide and name itLeave a space between the two names from steps 1 and 2.
5Other common names to learn: Alkyl HalidesOther common names to learn:8.1 Nomenclature
6IUPAC Naming RulesIdentify the longest carbon chain and name it as the parentContains double or triple bond if presentNumber the parent chain beginning at the end nearest any substituent (alkyl or halogen)If more than one of the same kind of substituent is present, number each and use the Greek prefixes to indicate how many
7If different substituents are equidistant from the ends of the parent chain, begin at the end nearer the substituent whose name comes first in the alphabet.
8ProblemsName the following alkyl halides using common nomenclatureName the following alkyl halides using IUPAC nomenclature:
9ProblemsCHCl3 is commonly known as chloroform. What is its IUPAC name?Based on what you know from question #1, what are the common and IUPAC names for CHBr3, CHI3, and CHF3?
10General Classifications Alkyl halides can be classifed as methyl, primary, secondary, or tertiary based on the number of organic groups bonded to the halogen bearing carbon8.1 Nomenclature
11ProblemDraw 4-chloro-3,4-dimethyl-1-octene. Classify this alkyl halide based on degree of substitution.
12Contain an OH group connected to a saturated (sp3-hybridized) Carbon AlcoholsContain an OH group connected to a saturated (sp3-hybridized) CarbonImportant solvents and synthesis intermediatesMethanol (Methyl Alcohol)Common solventFuel additiveEthanol (Ethyl Alcohol)SolventFuelBeverageIsopropanol (Isopropyl Alcohol)Rubbing alcoholDisinfectant
13PhenolsCompounds containing an OH group bonded to a carbon in a benzene ringBuilding polycarbonates, epoxies, Bakelite, nylon, detergents and a large collection of drugs, herbicides and pharmaceuticals.BPAEugenol
14Glycols Compounds containing two or more hyrodoxyl (-OH) groups Diol: contains two –OH groupsGeminal: OH’s are on the same carbonVicinal: OH’s are on adjacent carbonsGeneral: OH’s located in non-geminal/non-vicinal positionsEthylene GlycolResorcinol
17Common Naming Rules Used for simple and common alcohols Identify the alkyl group to which the hydroxyl group is attached and name this as a substituentEthane EthylAdd the word “Alcohol”
18IUPAC Naming RulesSelect the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the “-e” ending of the corresponding alkane with “-ol “Number the chain from the end nearest to the hydroxyl groupNumber substituents according to position on chain and then list them in alphabetical order as usual2-chloro-5-methyl-1-hexanolOr 2-chloro-5-methylhexan-1-ol
19If stereochemistry is known, indicate it If there are more than one hydroxyl groups, use Greek prefixes to indicate how manyDo not drop the final e of the alkaneIf stereochemistry is known, indicate it
20Naming PhenolsUse “phenol” (the French name for benzene) as the parent hydrocarbon name, not benzeneName substituents on aromatic ring by their position from OH
21Name the following molecules: ProblemsName the following molecules:Classify the first two molecules above based on level of substitution (1°, 2°, 3° alcohol)Draw the following molecules1,2,3-propanetriol2-ethyl-3-methylphenol
22ThiolsCompounds that contain a carbon bonded to a sulfhydryl group (-SH)Sulfur analogs of alcoholsR-SH vs. R-OHStinky moleculesAlso known as “Mercaptans”The –SH group is also called a “mercapto” groupEthanethiol vs Ethanol
23Nomenclature of Thiols Common:Named in the same fashion as alcoholsThe word mercaptan replaces alcohol in the name of the equivalent alcohol compoundExample: CH3SH would be methyl mercaptan, just as CH3OH is called methyl alcohol.Methyl mercaptanMethyl Alcohol
24IUPACIdentify the longest carbon chain containing the sulfhydryl group. Name this chain and add “thiol” to the end (no space).Number the chain so that the carbon connected to the –SH group has the lowest number possibleName and number all of the substituents and place them, in alphabetical order, in front of the parent chain name.2-hexanethiol2-ethyl-1-hexanethiol
25Name the following compounds: ProblemsName the following compounds:Draw:3,3-dimethyl-1-butanethiol2-ethylcyclohexanethiolTrans-3-heptene-2-thiol
27Principle Group and Principle Chain Principle Group: the functional group upon which the name of a molecule is basedCited as the suffix in the nameExample: PentanolHave priorities in a moleculeAll other substituents are cited as prefixes (except multiple bonds)Carboxylic acid > anhydride > ester > acid halide > amide > nitrile > aldehyde > ketone > alcohol/phenol > thiol > amine8.1 Nomenclature27
28Identify the principle group (e.g., -OH > -SH) Identify the principle chainThe carbon chain on which is the name is basedPriorities for picking the principle chain:The carbon chain with the greatest number of principle groupsThe carbon chain with the greatest number of double and triple bondsOf greatest lengthWith the greatest number of other substituents
29Principle Group and Principle Chain Number the carbons of the principle chain giving the lowest numbers:For the principle groupsFor multiple bonds (C=C > CC)For other substituentsFor the substituent cited first in the name8.1 Nomenclature29
30Principle Group and Principle Chain Begin construction of the name with the name of the hydrocarbon corresponding to the principle chainCite principle group by suffix and numberWill be last number in molecular nameIf there is no principle group, name the compound as a substituted hydrocarbonCite the names and numbers of other substituents in alphabetical order8.1 Nomenclature30