Question

Show the alkyl bromide and alcohol used to make methyl t-butyl ether using the Williamson ether synthesis to the right of the retrosynthetic arrow.

Mapoob a) Show the alkyl bromide and alcohol used to make methyl t-butyl ether using the Williamson ether synthesis to the right of the retrosynthetic arrow. alcohol alkyl bromide click to edit CHa H3 H3 b) Complete the general mechanism by adding curved arrows and drawing the final organic product. (Note that R is an abbreviation for any alkyl group and can be found on the bottom row in the pull down periodic table in the drawing tools menu.) product Na +RX Previous ⓧ Give Up & View Solution O Check Answer 0 Next Exit-

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Answer #1
Concepts and reason

• Retrosynthetic analysis: It is a way of planning an organic synthesis which involves the transformation of complex target molecules to simple precursor structures.

• Williamson’s ether synthesis is the reaction in which an alcohol is converted to ether. Nucleophilic substitution takes place between metal alkoxides and alkyl halides which results in ether product.

Fundamentals

For the retrosynthetic analysis, a retrosynthetic arrow should be used.

Retrosynthetic arrow:

Reaction mechanism gives a step – by – step explanation of how the product arrives from the starting material. The movement of electrons was indicated by the curved arrows (double – headed arrows).

This type of arrow is called a double – headed arrow (curved arrow), which is used for the movement of electrons in the mechanism.

(a)

CH3
CH3
Br
CH3
-
=
H2C
+
H3C
HC Too
CH3
O H
CH3
Alcohol
alkyl halide

(b)

Na
Nat
H-H
H
Nat :X?
H—H
R-3*
+RX, R-
RS
-
R--R

Ans: Part a

CH3
CH3
Br
CH3
-
=
H2C
+
H3C
HC Too
CH3
O H
CH3
Alcohol
alkyl halide

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