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Chapter 11
Alkenes: Infrared Spectroscopy & Mass Spectrometry
19
Organic Chemistry
Undergraduate 2
11/11/2014

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Term
pi bond
Definition
when p orbitals are aligned parallel to each other & are close enough to overlap; ex) part of the double bond between carbons in alkenes
Term
The electron density in a pi bond is distributed over both carbons _____ and _____ the molecular plane
Definition
above & below
Term
thermal isomerization
Definition
the process of measuring the energy required to interconvert the cis form of a substituted alkene with its trans isomer; used to predict pi bond strength; involves the two p orbitals making up the pi bond being rotated 180 degrees
Term
Which is stronger: a sigma bond or a pi bond?
Definition
a sigma bond
Term
Alkyl substituents are inductive _____ donors to the pi bond
Definition
electron
Term
hydrogenation
Definition
when an alkene and hydrogen gas are mixed in the presence of catalysts such as palladium or platinum, two hydrogen atoms add to the double bond to give the saturated alkane; very exothermic
Term
heat of hydrogenation
Definition
the heat released in hydrogenation; typically about 30kcal per double bond
Term
The most general approach to the formation of alkenes is _____, in which two adjacent groups on a carbon framework are removed
Definition
elimination
Term
regioselectivity
Definition
certain hydrogens are more likely to be eliminated in a reaction than others
Term
Elimination proceeds through attack by the base on one of the neighboring hydrogens situated _____ to the leaving group
Definition
anti
Term
Eliminations that lead to the more highly substituted alkene are called _____
Definition
Saytzev
Term
Saytzev rule
Definition
the double bond forms preferentially between the carbon that contained the leaving group & the most highly substituted adjacent carbon that bears a hydrogen
Term
The most stable alkene is formed by a double bond between the carbon containing the leaving group and _____
Definition
the most substituted carbon that also bears an elimination hydrogen
Term
When a bulky base is used, more of the _____ alkene is formed
Definition
Hofmann
Term
Why does the Hofmann alkene form when a bulky base is used?
Definition
the elimination hydrogens that are the least Sterically hindered (on the least substituted carbon) are attacked
Term
Hofmann rule
Definition
the alkene double bond will be formed between the carbon containing the leaving group and the least substituted adjacent carbon; thermodynamically less favored isomer is formed; named after chemist who did experiments on this type of reaction
Term
Before an E2 reaction takes place, bond rotation to an _____ conformation occurs
Definition
anti
Term
Are E2 reactions stereospecific?
Definition
yes
Term
dehydration
Definition
the treatment of alcohols with mineral acid at elevated temperatures to form alkenes by the loss of water; proceeds by E1 or E2
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