Structure and Synthesis of Alkenes
Alkenes (olefins) are hydrocarbons which have carbon–carbon double bonds. H
C C
H
H
H
A double bond is a σ bond and a π bond.
Double bond B.D.E. σ bond B.D.E.
= 146 kcal/mol
= 83 kcal/mol
Therefore π B.D.E. must = 63 kcal/mol.
A π bond is weaker than a σ bond. π Bonds are more reactive than σ bonds, and π bonds are considered to be a functional group.
Structure of Alkenes
In ethylene (ethene) each carbon is bonded to 3 other atoms, with zero nonbonding electrons => sp2 hybridization.
The C-H bonds are formed by overlap of sp2 orbitals from the Carbon overlapping with 1s orbital from the Hydrogen.
(The C-H bonds in ethane are sp3/1s overlapping orbitals. The ethene C-H bonds contain more s character than the ethane C-H bonds and are therefore shorter and stronger).
Ch07 Alkenes (Struct + synth)
Page1
H
1.33A
H
H
H
H
HH
1.08A
1.09A
HH
H
1.54A
sp2 are 1/3 s, whereas sp3 are 1/4 s in character. (s orbitals are closer to the nucleus and lower in energy).
The carbon-carbon bond in ethene is shorter and stronger than in ethane partly because of the sp2-sp2 overlap being stronger than sp3-sp3, but especially because of the extra π bond in ethene.
Double Bond
The unhybridized p orbitals on each carbon align parallel to form a π bond.
The π bond prevents rotation about the C=C bond because it would force the p orbitals into a non overlapping formation (i.e. break the π bond).
The π bond exists with half its electron density above the σ bond, and half below. Elements of Unsaturation
Alkanes are said to be saturated since they have they maximum number of bonds to hydrogen.
An alkene is unsaturated.
Ch07 Alkenes (Struct + synth)
Page2
Any π system or a ring system reduces the maximum number of hydrogens a molecule can have.
An element of unsaturation relates to 2 missing hydrogens from the saturated formula (CnH2n+2).
Consider alkane, alkenes and cycles:
H2
C
H3C CH2CH3 propane C3H8 saturated H2C CHCH3 propene C3H6 one element of unsaturation
H2C
CH2
cyclopropane
C3H6
one element of unsaturation
Heteroatom complications
Heteroatoms are considered anything other than C or H.
Halogens
These simply substitute for hydrogens in the molecular formula.
Therefore just like C2H6 is saturated, so is C2H4F2.
Oxygen
CH3-CH3 is saturated (C2H6)
CH3-O-CH3 is also saturated (C2H6O)
An oxygen can be added without requiring any additional hydrogens, so ignore the number of oxygens when calculating elements of Unsaturation.
Nitrogen
Nitrogen is trivalent, and when it replaces a C in a chain it requires only one hydrogen (-NH- vs. -CH2- ), so nitrogens count as half a carbon.
Thus C4H9N is equivalent to C4.5H9. (i.e. one element of Unsaturation).
Ch07 Alkenes (Struct + synth)
Page3
Nomenclature of Alkenes
Simple alkenes are named like alkanes (root from the longest carbon chain), but the –ane suffix is replaced by-ene.
H2C CH2 ethene H2C CHCH3 propene cyclohexene
When the chain is longer than 3 carbons, number the atoms such that the double bond is given the lowest number (i.e. start at the end nearest the double bond).
H
H2C C CH2CH3
1-butene
H H
H3C C C CH2CH3
2-pentene
Compounds with 2 double bonds are called dienes, 3 double bonds are trienes, etc.
H H
H2C C C CH2
1,3-butadiene 1,3,5,7-cyclooctatetraene
For branches, each alkyl group is given a number, but the double bond is still given preference when numbering the chain.
H H
H3C C C CH2
CH3
3-methyl-1-butene
When alkenes are substituents, they are termed alkenyl groups, and may be named systematically.
CH2
H
H2C C CH2
methylene 2-propenyl group group (allyl group)
Ch07 Alkenes (Struct + synth)
Page4
Geometric isomers
The rigidity of a π bond gives rise to geometric isomers.
When similar groups (not H’s) are bound to the same side of the double
bond
Related Documents: Chemistry: Alkene and Double Bond Essay
Chemistry is a critical concept to understand in Biology. Elements such as carbon, oxygen, and hydrogen comprise living organisms. These elements join together through various bonds to form organic molecules. Elements are substances that cannot be further broken down into other substances. Each element is made up of only one type of atom. An atom is the smallest unit of matter that still retains the properties of a specific element. Three subatomic particles comprise an atom: protons that have…
Chemistry Chapter 8 8.3 * Polarity * Flourine Chlorine and Bromine are all more electronegative than carbon, as a result the C-X bond is polarized, slightly positive charge on carbon and negative on the halogen. * Electronegativity of C is less than 2.5 which is why it is stil polar with I (2.5 also). * Boiling Point * Constitutional isomers with branched chains have lower boiling points than unbranched chains. * Branched chains have a more spherical arrangement…
carbon chain attached to the carboxylic will determine what type of fatty acid our body will have to deal with! An alkane carbon structure, classifies as a Saturated Fatty Acid, consuming large portions of alkenes causes fat to develop! Unsaturated fatty acids, which contain alkenes, are the main distinction between eating healthy or not. Cholesterol is the focus of our discussion at this point, as if treaded carefully can help you avoid many unfortunate conditions, such as blood clots,…
Synthetic and Bio-organic Chemistry (Weeks 7-12) 1.) Identify and define constitutional and stereoisomers. Constitutional: Two compounds have the same formula but different atom connections. Different chemical and physical properties. Example: n-butane and isobutane. Stereoisomers: Isomers with the same order of attachment of atoms in their molecules but a different orientation of their atoms or groups in space. For more, see part 2. 2.) Give examples of the following concepts. Stereocentre:…
Chemistry Notes HSC Core Topic 1 The Identification and Production of Materials Humans have always exploited their natural environment for all their needs including food, clothing and shelter. As the cultural development of humans continued, they looked for a greater variety of materials to cater for their needs. The twentieth century saw an explosion in both the use of traditional materials and in the research for development of a wider range of materials to satisfy the specialist needs of space…
Chemistry Notes [Exam2] Ionic and Covalent Bonding [Chaps 6.3-6.4] Opposites Attract Metal +Nonmetal=Ionic Bond Recall positive is attracted to negative charge When a metal atom donates an electron to a non-metal atom, an Ionic bond occurs Ionic Bonds are Predictable Ion charges of Calcium and Fluorine: Ca2+ F- Always from neutral compounds Al3+ and O2- These compounds are very stable over time Sharing can bring happiness In Ionic Bonding: The transfer of the electrons from one atom to a different…
Old Dominion University ORGANIC 214 Alkene Addition Submitted by: Alkene addition: Bromination of (E) Stilbene Introduction: In this lab we used the greener approach, which involves the addition of bromine across a double bond. When bromine reacts with E-stilbene (trans-1,2-diphenylethene), two new chiral carbons are created from the sp2 carbons, therefore 3 different dibrominated stereoisomers are possible: meso-(1R,2S), or the raceminc mixture-(1R,2R) or (1S,2S)-dibromo-1,2-diphenylethane…
Chemistry Exam Study Sheet Organic Chemistry • Study of compounds to which carbon is the principal element. • Carbon is special because it has 4 bonds. Functional Groups • Organic substances are organized into organic families. • Organic Families – group of organic compounds with common structural features. o Each family has a recognizable physical property and a specific structural arrangement. o Each combination is referred to as a functional group. o Even…
such as Oxygen, Nitrogen, Sulphur and Phosphorus also occur frequently. Knowledge of this chemistry is vital to the perfumer as it is the basis from which these aromas are created and to how the compounds are named and classified. This info is essential for everything from purchasing the raw materials to what will happen to the final aroma product. Carbon atoms are of unique character, in that they can bond with other carbon atoms to form chains, branched chains, ring structures, multiple-ring…
Unit 6: Synthesising Organic Compounds Assignment 6.1 Isomerism in Organic Chemistry arises when molecular formulae are the same, but the arrangement of atoms is different. Describing and explaining with examples, the different types of isomerism encountered in organic chemistry by focusing on: a) Structural: including function group isomerism Stereoisomerism: i.e. geometric and optical, with explanations of how this type of isomerism arises. You must use examples to explain. Structural Isomerism…