The most common method for synthesis of unsymmetrical ethers is the Williamson synthesis, a reaction (Sn2) of an alkoxide ion with an alkyl halide. Two pathwaysare possible, but one is preferred. Construct the preferred pathway for synthesis of 2-propoxypropane from propene-derived alkyl halide and alkoxide intermediates.
The concept used in the problem is of Williamson’s Synthesis. Williamson’s Synthesis or Williamson’s ether synthesis is very important and convenient method for the synthesis of simple and mixed ethers. As the unsymmetrical ether synthesis requires selectivity of the reactant to give the desired product. Several pathways are possible for the synthesis.
The Williamson’s ether synthesis involves the reaction of alkoxides and phenoxides with alkyl halides, which undergo bimolecular substitution reaction (SN2 reaction). In the asymmetric synthesis, there are two possibilities for the choice of reactants, which is more available and reactive to form desired product.
Since the preliminary requirement for the synthesis is the selection of correct reactant. In which alkoxide (deprotonated alcohol) or the phenoxide may be primary, secondary or tertiary depending upon the alcohol taken. Whereas the alkyl halide, are taken most preferably primary, because the reaction undergoes SN2 reaction in which the primary halides are more reactive.
As the alkoxide are very reactive in nature, so they are just prepared from the alcohol immediately before performing Williamson’s synthesis, by the use of strong base such as metal hydride, or carbonate base.
Alkyl halide can also be prepared from the hydro halogenation of alkene.
To obtain primary halide and the secondary alkoxide, propene must undergo different types of electrophilic addition reactions.
Firstly, the Markovnikov’s addition of (Reagent 1) to propene to get 2-propanol is done (Secondary alkoxide as Step 1 product).
To obtain 2-propoxypropane as the final desired product there must be a primary halide and secondary alkoxide as the reactant.
The primary halide can be obtained by Anti-Markovnikov addition of (Reagent 2) to propene to get 1-bromopropane (primary halide as Step 2 product).
This secondary alcohol is further treated with metal base (Reagent 3) to give the Sodium isopropoxide (secondary alkoxide as Step 3 product).
The secondary alkoxide ion attacks in the fashion on the orbital of the C-Br bond resulting in the breakage of the sigma bond between C-Br and simultaneously formation of the sigma bond between carbon and the upcoming nucleophile, in a concerted manner.
Resulting the formation of 2-propxypropane as the Williamson’s unsymmetrical ether.
Construct the preferred pathway for synthesis of 2-propoxypropane from propene-derived alkyl...
The most common method for the synthesis of unsymmetrical ethers
is the Williamson synthesis, a reaction (SN2) of an alkoxide ion
with an alkyl halide. Two pathways are possible, but often one is
preferred. Construct the preferred pathway for the synthesis of
2-propoxypropane from propene, with propene-derived alkyl halide
and alkoxide intermediates, by dragging the appropriate
intermediates and reagents into their bins. Not every given reagent
or intermediate will be used.
The most common method for the synthesis of unsymmetrical...
The most common method for synthesis of unsymmetrical ethers is
the Williamson synthesis, a reaction (Sn2) of an alkoxide ion with
an alkyl halide. Two pathways are possible, but one is preferred.
Construct the preferred pathway for synthesis of 2-propoxypropane
from propene-derived alkyl halide and alkoxide intermediates.
The most common method for the
synthesis of unsymmetrical ethers is the Williamson synthesis, a
reaction (SN2) of an alkoxide ion with an alkyl halide. Two
pathways are possible, but often one is preferred. Construct the
preferred pathway for the synthesis of 2-propoxypropane from
propene, with propene-derived alkyl halide and alkoxide
intermediates, by dragging the appropriate compounds into their
bins and selecting the reagents from the drop-down list.
The most common method for the synthesis of unsymmetrical ethers is the...
The most common method for the synthesis of unsymmetrical ethers is the Williamson synthesis, a reaction (Sn2) of an alkoxide ion with an alkyl halide. Two pathways are possible, but often one is preferred. Construct the preferred pathway for the synthesis of 2-propoxypropane from propene, with propene-derived alkyl halide and alkoxide intermediates, by dragging the appropriate intermediates and reagents into their bins. Not every given reagent or intermediate will be used.
The most common method for the synthesis of unsymmetrical ethers
is the Williamson synthesis, a reaction (SN2) of an alkoxide ion
with an alkyl halide. Two pathways are possible, but often one is
preferred. Construct the preferred pathway for the synthesis of
2-propoxypropane from propene, with propene-derived alkyl halide
and alkoxide intermediates, by dragging the appropriate
intermediates and reagents into their bins. Not every given reagent
or intermediate will be used.
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The most common method for the synthesis of unsymmetrical ethers is the Williamson synthesis, a reaction (SN2) of an alkoxide ion with an alkyl halide. Two pathways are possible, but often one is preferred. Construct the preferred pathway for the synthesis of 2-propoxypropane from propene, with propene-derived alkyl halide and alkoxide intermediates, by dragging the appropriate compounds into their bins and selecting the reagents from the drop-down list.
The most common method for the synthesis of unsymmetrical ethers is the Williamson synthesis, a reaction (Sn2) of an alkoxide ion with an alkyl halide. Two pathways are possible, but often one is preferred. Construct the preferred pathway for the synthesis of 2-propoxypropane from propene, with propene-derived alkyl halide and alkoxide intermediates, by dragging the appropriate compounds into their bins and selecting the reagents from the drop-down list.
The most common method for the synthesis of unsymmetrical ethers
is the Williamson synthesis, a reaction (SN2) of an alkoxide ion
with an alkyl halide. Two pathways are possible, but often one is
preferred. Construct the preferred pathway for the synthesis of
2-propoxypropane from propene, with propene-derived alkyl halide
and alkoxide intermediates, by dragging the appropriate compounds
into their bins and selecting the reagents from the drop-down
list.
1. Unsymmetrical ethers can be made by the Williamson synthesis, in which an alkoxide ion reacts with an alkyl bromide. Draw the structure of the alkoxide and the alkyl bromide needed to produce 2-ethoxy-2-methylpropane (a.k.a t-butyl ethyl ether), shown below. Show charges where appropriate.HINT:The reaction involves an SN2 attack of the alkoxide on the alkyl bromide, displacing the bromide ion.R1O- + R2Br --------> R1-0-R2 + Br-What are the alkyl groups found in the ether? One alkyl group will come from...
reaction of a ........with an alkyl halide, 19. The Williamson ether synthesis consists of an alkyl sulfonate, or alkyl sulfate. A SNI, sodium chloride B. SN2, sodium alkoxide C. El sodium chloride DE2, sodium chloride 20. Which of the following statements is not true regarding oxymersuration- demecution? A. They are regioselective reactions. B. The net reaction does not follow Markoynikey's Rule in its original statement. C. The reducing reagent NaBH, is involved in demersuration D. Water is required for the...