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’s 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

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

(c)

(d) meso-hexane-3,4-diol

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?

Question:Show how you would accomplish the following synthetic transformations. Show all intermediates.

(a)2,2-dibromobutane→but-1-yne

(b)2,2-dibromobutane→but-2-yne

(c)but-1-yne→oct-3-yne

(d)trans-hex-2-ene→hex-2-yne

(e)2,2-dibromohexane→hex-1-yne

(f)cyclodecyne→cis-cyclodecene

(g)cyclodecyne→trans-cyclodecene

(h)hex-1-yne→hexan-2-one, CH3COCH2CH2CH2CH3

(i)hex-1-yne→hexanal, CH3(CH2)4CHO

(j)trans-hex-2-ene→cis-hex-2-ene

Question:The application box in the margin of page 473 states, “The 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.” Show how you would accomplish this synthesis from acetylene and a carbonyl compound.

ethchlorvynol

Question: Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents.

(a) prop-2-yn-1-ol (propargyl alcohol)

(b) hept-2-yn-4-ol

(c) 2-phenylbut-3-yn-2-ol

(d) 3-methylhex-4-yn-3-ol

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