Show how to convert 1-butyne to the following product: (Specify the reagents you

Question

Show how to convert 1-butyne to the following product:

(Specify the reagents you would use to carry out the conversion by using letters from the table. The reaction may require more than one step, if so, write the letters in the order that they are used, e.g., ef. If two or more ways of conversion to the same product are possible, show only one of them.)

The reagents are:

Reagents available a. 2 mol e. / (liq) i. 2 mol / b. , , f. j. 2 mol / (liq) c. g. k. (ethanol) d. 2 mol

h. / Lindlar catalyst

l. 1.

2. , ,

Explanation / Answer

NaNH2 (1-Butene)
CH3CH2CH2CH2Cl --------------> CH3CH2CH=CH2 + HCl

Br2, CCl4
CH3CH2CH=CH2 ---------------> CH3CH2CH(Br)CH2Br (Simple addition Reaction)

NaNH2 (1-Butyne)
CH3CH2CH(Br)CH2Br ----------------> CH3CH2C?CH + 2HBr

Remember Sodamide (NaNH2) is a very strong base and generally results in Terminal Alkynes when treated with Vicinal Dihalides like the last step of the reaction above. Alcoholic KOH on the other hand results in the formation of Alkynes with triple bonds in the middle of the molecule.

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