HYDROCARBONS structure and naming of alkanes, alkenes, and alkynes Learning • To explain the distinct properties of Outcomes alkanes, alkenes, and alkynes • To differentiate alkanes, alkenes and Organic Chemistry alkynes.
Hydrocarbons Hydrocarbons: ALKANES
is an organic chemical compounds composed are organic compounds that consist entirely of exclusively of C and H atoms single-bonded carbon and hydrogen atoms and lack any other functional groups C L A ALKANES hydrocarbons that lack π bonds are called saturated S S hydrocarbons I F ALKENES I general formula: CnH2n+2 , where n = integer C A T ALKYNES EXAMPLE: I O CH4 C(1)H2(1)+2 CH4 N S AROMATIC C4H10 C(4)H2(4)+2 C4H10 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
Organic compounds have common names given by the person who discovered or made such compounds. NOMENCLATURE of Alkanes: Millions of organic compounds systematic name I. Identify the parent choose the longest chain IUPAC International Union of Pure and Applied Chemistry proposed a system of nomenclature for organic molecules
Parent Chain = 9 atoms
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
I. Identify the parent choose the longest chain I. Identify the parent choose the longest chain
If there is a competition between two chains of equal length,
choose the chain with the greater number of substituents.
Substituents are the groups connected to the parent
chain 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
I. Identify the parent choose the I. Identify the parent choose the longest chain longest chain “cyclo” is used to indicate the presence of a ring in the structure of an alkane
Examples of Cycloalkanes
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
II. Identify and name the substituents II. Name the substituents same terminology with the parent name but with “-yl” 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
II. Identify and name the substituents II. Identify and name the substituents When an alkyl group is connected to a ring, the ring is Only true when the ring is comprised of more carbon generally treated as the parent: atoms than the alkyl group:
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
III. Number the parent chain and assign a locant to each III. Number the parent chain and assign a locant to each substituent. substituent.
• If one substituent is present, it should be assigned the • When multiple substituents are present, assign numbers so that lower possible number. the first substituent receives the lower number. 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes: III. Number the parent chain and assign a locant to each III. Number the parent chain and assign a locant to each substituent. substituent.
• If there is a tie, then the second locant should be as low • When dealing with cycloalkanes, all of the same rules apply: as possible:
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes: III. Number the parent chain and assign a locant to each III. Number the parent chain and assign a locant to each substituent. substituent.
• Prefix is used to identify how many times that substituent NOTE: hyphen is used to separate numbers from letters, while appears in the compound commas are used to separate two numbers from each other (di = 2, tri = 3, tetra= 4, penta = 5, and hexa = 6) 1,1,3-trimethylcyclohexane 1,1,3-trimethylcyclohexane 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes:
IV. Arrange the substituents alphabetically. Provide a systematic name for the following compound: Place locants in front of each substituent. For identical substituents, use di, tri, or tetra, which are ignored in alphabetizing.
In otherwords, “dimethyl” is alphabetized as if it started with
the letter “m” rather than “d.”
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
NOMENCLATURE of Alkanes: NOMENCLATURE of Alkanes: STEP I. Identify the parent chain STEP III. Assign the locants. STEP II. Identify and name the substituents. STEP IV. Arrange substituents in alphabetical order. 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
CHARACTERISTICS of Alkanes: CHARACTERISTICS of Alkanes:
Alkanes = “paraffin” slight affinity unreactive A. Chemical Reactions:
A. Chemical Reactions: • Halogenation Reaction reaction with halogens (radical
CHARACTERISTICS of Alkanes: CHARACTERISTICS of Alkanes: B. Boiling Point and Melting Point B. Boiling Point and Melting Point • Straight-Chain Alkanes increasing number of C, increasing BP and MP increases molecular size thus increasing strength of IMF BP: -161 OC • Branched-Chain Alkanes lower BP and MP compared to straight-chain alkane counterpart BP: 36 OC branching decreases surface area thus decreasing strength of IMF BP: 9.5 OC 22/11/2024
Hydrocarbons: ALKANES Hydrocarbons: ALKANES
SOURCES and USES of Alkanes: Main source of alkanes petroleum CRACKING is a process by which C-C bonds of larger alkanes are broken, producing smaller alkanes suitable for gasoline.
can be achieved at high temperature (thermal cracking)
or with the aid of catalysts (catalytic cracking).
are unsaturated compounds with at least one carbon-to-carbon NOMENCLATURE of Alkenes:
double bond commonly prepared via elimination reactions replace the “-ane” with “-ene” to indicate the presence of C = C general formula: CnH2n , where n = integer double bond
EXAMPLE:
C2H4 C(2)H2(2) CH4
abundant in nature and an important
precursor in the chemical industry 22/11/2024
Hydrocarbons: ALKENES Hydrocarbons: ALKENES
NOMENCLATURE of Alkenes: NOMENCLATURE of Alkenes:
use the longest chain that includes when numbering the parent chain of an alkene, the π bond the π bond should receive the lowest number possible despite the presence of alkyl substituents:
Hydrocarbons: ALKENES Hydrocarbons: ALKENES
NOMENCLATURE of Alkenes: NOMENCLATURE of Alkenes:
the position of the double bond is indicated using a Provide a systematic name for the following compound: single locant, rather than two locants. 22/11/2024
Hydrocarbons: ALKENES Hydrocarbons: ALKENES
NOMENCLATURE of Alkenes: NOMENCLATURE of Alkenes: STEP I. Identify the parent chain STEP III. Assign the locants. STEP II. Identify and name the substituents. STEP IV. Arrange substituents in alphabetical order.
3,4-diethyl-2,5-dimethyl-2-heptene
Hydrocarbons: ALKENES Hydrocarbons: ALKENES
NOMENCLATURE of Alkenes: NOMENCLATURE of Alkenes: STEREOISOMERS cis- (same side) classified by the degree of substitution • Using cis- and trans- designation: trans-(opposite side) 22/11/2024
Hydrocarbons: ALKENES Hydrocarbons: ALKENES
STEREOISOMERS CHARACTERISTICS of Alkenes: NOMENCLATURE of Alkenes: E- “entgegen” opposite Z- “Zusammen” same Alkenes = “olefins” soot (alkene) is more smoky • Using E and Z designation: compare with alkanes A. Chemical Reactions: • Combustion reaction with oxygen Complete Combustion (enough O2): C2H4 + 3O2 2CO2 + 2 H2O Incomplete Combustion (not enough O2): Priority is assigned based on atomic number C2H4 + O2 C + CO + CO2 + H2O
Hydrocarbons: ALKENES CHARACTERISTICS of Alkenes: A. Chemical Reactions: • Addition Reaction addition of two groups across a double bond 22/11/2024
Hydrocarbons: ALKENES Hydrocarbons: ALKYNES
CHARACTERISTICS of Alkenes: are unsaturated compounds with at least one carbon-to-carbon triple bond C≡C A. Chemical Reactions: less common in nature than alkenes • Polymerization Reaction is a process of producing larger molecules from repeating units general formula: CnH2n-2 , where n = integer
EXAMPLE: C2H2 C(2)H2(2)-2 C2H2
Hydrocarbons: ALKYNES Hydrocarbons: ALKYNES
Can be classified as: NOMENCLATURE of Alkenes:
a) Terminal alkynes monosubstituted alkynes replace the “-ene” with “-yne” to indicate the presence of C≡C double bond b) Internal alkynes disubstituted alkynes the rest of rules for naming alkenes and alkanes are followed 22/11/2024
Hydrocarbons: ALKYNES
NOMENCLATURE of Alkynes:
Provide a systematic name for the following compound:
Hydrocarbons: ALKYNES Hydrocarbons: ALKYNES
NOMENCLATURE of Alkynes: NOMENCLATURE of Alkynes: STEP I. Identify the parent chain STEP III. Assign the locants. STEP II. Identify and name the substituents. STEP IV. Arrange substituents in alphabetical order.
4-Ethyl-5-methyl-3-propyl-1-heptyne 22/11/2024
Hydrocarbons: ALKYNES Hydrocarbons: ALKYNES CHARACTERISTICS of Alkynes: Alkynes = “acetylene” CHARACTERISTICS of Alkynes: B. Boiling Point and Melting Point A. Chemical Reactions: Hydrocarbons with the same number of carbon atoms (lighter • Combustion reaction with oxygen same products with alkanes and alkenes for weight): Alkynes > Alkanes > Alkenes both types of combustion soot are relatively thicker than the alkenes alkanes have 2 more hydrogens compared to alkenes
Alkynes undergo many of the same addition reactions as alkynes have triple bonds thus more polarizable alkenes. compared to alkanes and alkenes
