780 likes | 982 Views
Classes of Hydrocarbons. Hydrocarbons. Aliphatic. Aromatic. Hydrocarbons. Aliphatic. Aromatic. Alkanes. Alkenes. Alkynes. H. H. H. H. C. C. H. H. Hydrocarbons. Alkanes are hydrocarbons in which all of the bonds are single bonds. Aliphatic. Alkanes. H. H. C. C. H. H.
E N D
Hydrocarbons Aliphatic Aromatic
Hydrocarbons Aliphatic Aromatic Alkanes Alkenes Alkynes
H H H H C C H H Hydrocarbons Alkanes are hydrocarbons in which all of the bonds are single bonds. Aliphatic Alkanes
H H C C H H Hydrocarbons Alkenes are hydrocarbons that contain a carbon-carbon double bond. Aliphatic Alkenes
HC CH Hydrocarbons Alkynes are hydrocarbons that contain a carbon-carbon triple bond. Aliphatic Alkynes
H H H H H H Hydrocarbons The most common aromatic hydrocarbons are those that contain a benzene ring. Aromatic
Reactive Sites in Hydrocarbons The Functional Group Concept
Functional Group a structural unit in a molecule responsible for itscharacteristic chemical behavior and its spectroscopic characteristics
R—H R—X Alkanes functional group is a hydrogen atom the reaction that takes place is termed a substitution one of the hydrogens is substitutedby some other atom or group, X
R—H R—X H H H H Cl H H H C C C C H H H H Alkanes functional group is a hydrogen the reaction that takes place is substitution one of the hydrogens is substituted by some other atom or group + HCl + Cl2
Functional Groups in Hydrocarbons alkanes RH alkenes RH, double bond alkynes RH, triple bond aromatics ArH, double bond
Families of organic compounds and their functional groups Alcohols ROH Alkyl halides RX (X = F, Cl, Br, I) Amines primary amine: RNH2 secondary amine: R2NH tertiary amine: R3N Ethers ROR
O O C C Many classes of organic compounds contain a carbonyl group R Carbonyl group Acyl group
O O C C Many classes of organic compounds contain a carbonyl group H R Carbonyl group Aldehyde
O O C C Many classes of organic compounds contain a carbonyl group R' R Carbonyl group Ketone
O O C C Many classes of organic compounds contain a carbonyl group OH R Carbonyl group Carboxylic acid
O O C C Many classes of organic compounds contain a carbonyl group OR' R Ester Carbonyl group
O O C C Many classes of organic compounds contain a carbonyl group NH2 R Amide Carbonyl group
General formula for an alkane CnH2n+2 Introduction to Alkanes: Methane, CH4 Ethane, C2H6 Propane, C3H8
The simplest alkanes Methane (CH4) CH4 Ethane (C2H6) CH3CH3 Propane (C3H8) CH3CH2CH3 bp -160°C bp -89°C bp -42°C No isomers possible for C1, C2, C3 hydrocarbons
Isomeric Alkanes: The Butanes C4H10 General formula for any butane
C4H10 n-Butane Isobutane CH3CH2CH2CH3 (CH3)3CH bp -0.4°C bp -10.2°C
Higher n-Alkanes Pentane (C5H12) and Beyond CnH2n+2 n > 4
CnH2n+2 n > 4 CH3CH2CH2CH2CH3 n-Pentane CH3CH2CH2CH2CH2CH3 n-Hexane CH3CH2CH2CH2CH2CH2CH3 n-Heptane
C5H12 (CH3)2CHCH2CH3 CH3CH2CH2CH2CH3 Isopentane n-Pentane (CH3)4C Neopentane
How many isomers? The number of isomeric alkanes increases as the number of carbons increase. There is no simple way to predict how many isomers there are for a particular molecular formula.
Table 2.3 Number of Constitutionally Isomeric Alkanes CH4 1 C2H6 1 C3H8 1 C4H10 2 C5H12 3 C6H14 5 C7H16 9
Table 2.3 Number of Constitutionally Isomeric Alkanes CH4 1 C8H18 18 C2H6 1 C9H20 35 C3H8 1 C10H22 75 C4H10 2 C15H32 4,347 C5H12 3 C20H42 366,319 C6H14 5 C40H82 62,491,178,805,831 C7H16 9
C6H6 Isomers How many isomers with the composition C6H6 can you draw?
C6H6 Isomers: How many isomers with the compositionC6H6 can you draw?
Structure of Ethylene bond angles: H-C-H = 117° H-C-C = 121° bond distances: C—H = 110 pm C=C = 134 pm planar
Bonding in Ethylene Framework of s bonds Each carbon is sp2 hybridized s s s s s
Bonding in Ethylene Each carbon has a half-filled p orbital
Bonding in Ethylene Side-by-side overlap of half-filled p orbitals gives a p bond
Isomers Isomers are different compounds thathave the same molecular formula (composition).
Isomers Constitutional isomers Stereoisomers
Isomers Constitutional isomers Stereoisomers same connectivity; different arrangementof atoms in space different connectivity
Isomers Constitutional isomers Stereoisomers consider the isomeric alkenes of molecular formula C4H8
H3C H CH2CH3 H C C C C H3C H H H H3C CH3 H H3C C C C C H H H CH3 1-Butene 2-Methylpropene trans-2-Butene cis-2-Butene
H3C H CH2CH3 H C C C C H3C H H H H3C CH3 C C H H 1-Butene 2-Methylpropene Constitutional isomers cis-2-Butene
H3C H CH2CH3 H C C C C H3C H H H H H3C C C H CH3 1-Butene 2-Methylpropene Constitutional isomers trans-2-Butene
H3C CH3 H H3C C C C C H H H CH3 Stereoisomers trans-2-Butene cis-2-Butene
Chirality A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable.
Bromochlorofluoromethane is chiral It cannot be superposed point for point on its mirror image. Cl Br H F