Chapter 5 Notes: Alkene Structure, Elimination Reactions

Alkenes

• C=C double bond
• Cn H2n - general formula
• unsaturated
  not "saturated" with maximum hydrogens
  unsaturated fats have some double bonds (easier to digest)
• note that cycloalkanes also are Cn H2n

• alkenes & polyenes (dienes, trienes, etc.)
• arenes - aromatic rings
• alkynes - triple bonds
• combinations - e.g., enynes

• multiple bonds are stronger
• shorter bonds are stronger

• parent alkene is the longest continuous carbon chain that includes the double bond
• number from the end that gives the double bond the lower number
• use -en- instead of -an-
• use only the first number of the double bond
• name substituents as usual

• double bond assumed at C1-C2
• number in the direction that gives substituents lower numbers

3-methylcyclohexene

5,5-dimethyl-1,3-cyclopentadiene

• C=C double bond is one sigma bond and one pi bond
• sp2 hybridization (trigonal planar)
• pi bond doesn't rotate
• unlike ethane, ethene has no other conformers

• another example of stereoisomers
• 2-butene has two isomers:

trans-2-butene

cis-2-butene

• an alkene can have cis-trans isomers only when each C in the double bond is attached to 2 different groups

cis or trans ?

• note that cis-trans works unambiguously only for disubstituted alkenes
• cis and trans can be used to follow the structure of the parent chain in some cases
• E,Z designation is more general and always works

• assign priorities to the two groups on each C of the double bond
  ( one high priority, one low priority for each C )
• if the the two high priority groups are on the same side, it is Z
• if the the two high priority groups are on opposite sides, it is E

• consider just each atom bonded to the C
• higher atomic number is higher priority
• for a tie, consider each atom bonded next in turn
• for a double bond, consider it like two identical atoms

(E)-3,4-dimethyl-2-octene

(Z)

• greater substitution leads to greater stability
• tetrasubstituted > trisubstituted > disubstituted > monosubstituted
• trans typically more stable than cis

• dehydrogenation (loss of H2 from an alkane)
• dehydration (loss of H2O from an alcohol)
• dehydrohalogenation (loss of HX from an alkyl halide)

• regioselectivity - Zaitsev Rule (prefer more stable alkene)
• stereoselectivity
• mechanism - carbocation intermediate
• reactivity: 3° > 2° > 1°
• carbocation rearrangements - hydride shifts, alkyl shifts

• base-promoted elimination
• E2 mechanism - concerted, bimolecular
• stereoselectivity - anti elimination
• E1 elimination for 3° alkyl halides in absence of base

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