many compounds can eliminate in more than one way, to give __.
In most E1 and E2 eliminations where there are two or more possible elimination products, the product will be what?
This general principle is called __ and reactions that give the most usbstituted alkene are said to follow __.
mixtures of alkenes
will be the one with the msot substituted double bonds
Zaitsev's rule
Zaitsev orientation
Zaitsev's rule
in elim reactions, teh most subst. alkene usually predominates
True or False:
Eliminatiosn can also take place under second order conditions with a strong base present.
The rate of the elimination is proportional to the concentrations of both the __ and the __, giving a __. This is a __ process, with both the base and the alkyl halide participating in the __, so this mechanism is abbreviated __ for __.
True
alkyl halide
base
second order rate equation
bimolecular
TS
E2
elimination, bimolecular
Most strong nucleophiles are also strong bases, and elimination commonly results when a strong base/ nucleophile is used witha __ such as a tertiary or hindered secondary alkyl halide. instead of attacking the baci side of hte hindered __, for example, methoxide abstracts a proton from one of hte methyl groups. ONE STEP
poor Sn2 substrate
electrophilic carbon
In the general mechanism of hte E2 reaction, a strong base abstracts a proton on a carbon atom adjacent to the one with the __. As the base abstracts a proton, a __ form s adn the the leaving group leaves. Like the Sn2 reaction, the E2 is a __ reaction in which bonds break and new bonds form at the same time, in a single step.
leaving group
double bond
concerted
The order of reactivity of alkyl halides towards E2 dehydrohalogenation is found to be __.
This reactivity order reflects the greater stablilty of __. Elimination of a tertiary halide gives a more __ than elim of a secondary halide, which gives a more __ than a primary.
The stabilities of the alkene products are reflected in the __, giving __ and __ that lead to highly substituted alkenes.
teritary > secondary> primary
substituted alkene x2
Tses
lower Ea
higher rates for elimination of alkyl halides
The E2 reation requires abstraction of a proton a carbon atom __. If tehre are two or more possibilities, __ may result. In most cases, __ predicts which of the possible products will be the major product: __
next to the carbon bearing hte halogen
mixtures of products
Zaitsev's rule
most subs. alkene
Key mechanism of E2
signle step: strong base abstracts a proton on a carbon next tot he leaving group, and the leaving group leaves--> alkene
Like the Sn2 reaction, the E2 follows a __: bond breaking and bond formation take place simultaneousyl, adn the partial formaiton of new bonds does what?.
concerted mechanism
lowers the energy of the transiton
__ require specific geometric arrangements so tha tthe orbitals of the bonds being broken can __with those being formed and hte electrons can flow smoothly from one bond to another.
The geometric arrangemnet required by Sn2 is a __; with teh E2, a __ is needed.
concerted mechanisms
overlap
backside attack
coplanar arrangement of the orbitals
E2 elim requires partial formation of a new __, with its parallel p orbitals in the TS. The electrons that once formed a C-H bond must begin to __ with the orbital the the __ is vacating. Formation of this new __ implies that these two sp3 orbitals must be __ so that pi overlap is possible as the H and halogen leave and hte orbitals rehybridize to the p orbitals of hte new pi bond.
pi bond
overlap
leaving group
pi bond
parallel
When th hydrogen and the halogen are __ to each other, their orbitals are aligned.
This is called the __ conformation. When teh hydrogen and hte halogen __each other, their orbitals are once again aligned. This is called the __ conformation.
anti
anti-coplanr
eclipse
syn-coplanar
Of these possible conformations, the __ is most commonly seen in E2 reactions. The transition state for __ is staggered, with the base far away from the leaving group. In most cases, this transition state is __ than that of the __.
anticoplanar
the anti coplanar
lower in energy
syn-coplanar elimination
The transition stae for __ is an eclipsed conformation. In addition to the higher energy resulting from eclipsign interactions, the transition state suffers from __ between the __ and the __. To abstract the proton, the base must approach quite close to the __. In most cases, the __ is bulky and - charged, and the repulsion between the base and the leaving group raises the energy of the __.
syn-coplanar elimination
interference
leaving grop adn the attacking base
leaving group x2
syn coplanar TS
Some molecuels are rigidly held in __ with a H and a leaving group in a __> Such compounds are likely to udnergo __ by a __.
eclipsed (or nearly) conformations
syn-coplanar arrangement
E2 elimination
concerted syn-coplanar mechanism
The E2 is a __ reaction, because different stereoisomers of the starting material react to give different __ of the product. This __results from the __ that is usually involved int eh E2.