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

Write structural formulas for the following compounds (includes both old- and new-style names).

(a) 2-octyne (b) ethyl isopentyl acetylene (c) ethynylbenzene

(d) cyclohexyl acetylene (e) 5-methyl-3-octyne (f) trans-3,5-dibromocyclodecyne

(g) 5,5-dibromo-4-phenylcyclooct-1-yne (h) (E)-6-ethyloct-2-en-4-yne

(i) 1,4-heptadiyne (j) vinylacetylene (k) (S)-3-methyl-1-penten-4-yne

The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.

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: Predict the products of the following acid-base reactions, or indicate if no significant reaction would take place.

(a)H-C≡C-H+NaNH2(b)H-CC-H+CH3Li(c)H-CC-H+NaOCH3(d)H-CC-H+NaOH(e)H-CCNa++NaOH(f)H-CCNa++H2O(g)H-CCNa++H2C=CH2(h)H2C=CH2+NaNH2(i)CH3OH+NaNH2

The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

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