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.
• 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.
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)
(b)
Ans: Part a
Show the alkyl bromide and alcohol used to make methyl t-butyl ether using the Williamson ether...
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. 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.)
Could the Williamson Ether synthesis be carried out using any type of alkyl halide? Why/why not. Draw the mechanism for the Williamson Ether reaction using bromoethane and t-butyl bromide and relate it to your answer.
Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. . You do not have to consider stereochemistry . Do not include counter-ions, e.g., Na, I, in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner Separate structures with+ signs from the drop-down menu. ChemDoodle Retry Entire Group 9 more group attempts remaining Submit Answer
Part II. Competing nucleophiles with t-butyl alcohol 1. The composition of the product mixture is analyzed based on refractive index measurem. At 20.0 °C, the refractive index of puret-butyl chloride is 1.3877 and that of pure 1-buty bromide is 1.4280. One previous student determined the refractive index of his product mixture to be 1.4250 at 20.0 °C. Assume a linear relation between the refractive index and the molar composition of the mixture. Calculate the molar percentages of t-butyl chloride and/-butyl...
1. [10 pts] Consider the elimination reaction for the following alkyl halide with sodium methoxide in methanol (Na* OCH, CH,OH). CH NaOme MeOH CH Compound A Problem 2c Draw the major expected organic product (a) Redraw Compound A as seen in Viewpoint I below left as a Newman projection on the template provided in Problem 2a (below). Hint: Fill in missing Hs ar C2 and C3 to help you get started! (b) Rotate the C2 C3 bond to obtain the...