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Show how hex-1-yne might be converted to

(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.

(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.

(e) 2-bromohexane. (f) 2,2-dibromohexane.

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Step-by-Step SolutionStep 1: Organic Conversion

Organic conversion is the conversion of one particular functional group to another functional group present in a chemical compound that is facilitated with the help of a particular organic reagent and solvent.

The organic conversion method is used in the chemical industry for the formation of desired carbon compounds.

02

Conversion of reactant hex-1-yne in given products

(a) Halogenation of Hex-1yne with one mole of chlorine (Cl2)forms 1,2-dichlorohex-1-ene.

Formation of 1,2-dichlorohex-1-ene.

(b) Addition of hydrogen halide HBr in presence of peroxide in Hex-1yne forms 1-bromohex-1-ene.

Formation of 1-bromohex-1-ene.


(c) Addition of one mole of hydrogen halide HBr in Hex-1yne forms 2-bromohex-1-ene.

Formation of 2-bromohex-1-ene

(d) Halogenation of Hex-1yne with two moles of chlorine (Cl2)in presence of CCl4forms 1,1,2,2-tetrabromohexane.

Formation of 1,1,2,2-tetrabromohexane

(e) Hydrogenation of Hex-1yne with Lindlar鈥檚 catalyst or treating it with sodium metal in liquid ammonia (Na/NH3)first form hex-1-ene then adding one mole of hydrogen halide HBr in hex-1-ene forms 2-bromohexane.

Formation of 2-bromohexane

(f) Addition of 2 moles of hydrogen halide HBr in Hex-1yne forms 2,2-dibromohexane.

Formation of 2,2-dibromohexane

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Most popular questions from this chapter

Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.

(a)Upon catalytic hydrogenation, unknown Wgives cyclooctane. Ozonolysis of W,followed by reduction with dimethylsulfide, gives octanedioic acid,HOOC-(CH2) 6-COOH . Draw the structure of W.

(b)Upon catalytic hydrogenation, unknown Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.

(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.

(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.

Question:The application box in the margin of page 473 states, 鈥淭he addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.鈥 Show how you would accomplish this synthesis from acetylene and a carbonyl compound.

ethchlorvynol

Question:Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem)

(a)1,2-dibromohexane

(b)hex-1-yne

(c)2,2-dibromohexane

(d)hex-2-yne

(e)hexan-2-one

(f)hexanal

(g)pentanoic acid

(h)pentanal

(i)undec-6-yn-5-ol

The following functional group interchange is a useful synthesis of aldehydes.

(a)What reagents were used in this chapter for this transformation? Give an example to illustrate this method.

(b)This functional group interchange can also be accomplished using the following sequence.

Propose mechanisms from these steps.

(c) Explain why a nucleophilic reagent such as ethoxide adds to an alkyne more easily than it adds to an alkene.

Question:When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

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