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Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Short Answer

Expert verified

A hydrocarbon compound that exists in a gaseous state with molecular formula C2 H2 is acetylene. Thisorganic compound is used in fuels and some organic synthesis. In pure form, acetylene is unstable and has no odo

Step by step solution

01

About acetylene

A hydrocarbon compound that exists in a gaseous state with molecular formula C2 H2 is acetylene. Thisorganic compound is used in fuels and some organic synthesis. In pure form, acetylene is unstable and has no odo

02

(a) Synthesis of hex-1-yne

The acetylene is treated with sodium amide that will lead to the formation of a sodium salt. This salt is treated with bromobutane that result in the formation of hex-1-yne. The reaction is shown below.

03

(b) Synthesis of hex-2-yne

Theacetylene is treated with sodium amide that will lead to the formation of a sodium salt. This salt is treated with bromopropane that result in the formation of pent-1-yne. This compound is treated withmethyl iodide. This will result in the formation of hex-2-yne. The reaction is shown below.

04

(c) Synthesis of cis-hex-2-ene

The hex-2-yne synthesized in part (b) is treated with hydrogen in the presence of Lindlar鈥檚 catalyst. This will result in the formation of cis-hex-2-ene. The reaction is shown below.

05

(d) Synthesis of trans-hex-2-ene

The hex-2-yne synthesized in part (b) is treated with ammonia in the presence of sodium metal. This will result in the formation of trans-hex-2-ene. The reaction is shown below.

06

(e) Synthesis of 1,1-dibromohexane

The hex-1-yne synthesized in part (a) is treated with 2 equivalent of bromine in the presence of hydrogen peroxide. This will result in the formation of 1,1-dibromohexane. The reaction is shown below.

07

(f) Synthesis of 2,2-dibromohexane

The hex-1-yne synthesized in part (a) is treated with 2 equivalent of bromine in the basence of hydrogen peroxide. This will result in the formation of 2,2-dibromohexane. The reaction is shown below.

08

(g) Synthesis of pentanal

The hex-2-yne synthesized in part (b) is treated with followed by treatment with hydrogen peroxide and a base. This will result in the formation of pentanal. The reaction is shown below.

09

(h) Synthesis of pentan-2-one

Thehex-2-yne synthesized in part (b) is treated with water, sulphuric acid, and mercuric sulfate. This will result in the formation of pentan-2-one. The reaction is shown below.

10

(i) Synthesis of (+/-)-3,4-dibromohexane

The acetylene is treated with sodium amide that will lead to the formation of a sodium salt. This salt is treated with bromoethane that result in the formation of but-1-yne. This compound is treated withbromoethane leading to the formation of hex-3-yne. This is treated with hydrogen in the presence of Lindlar鈥檚 catalyst that forms This will result in the formation of hex-3-ene. This compound is treated with bromine leading to the formation of (+/-)-3,4-dibromohexane. The reaction is shown below.

11

(j) Synthesis of meso-butan-2,3-diol

The acetylene is treated with sodium amide that will lead to the formation of a sodium salt. This salt is treated with methyl iodide that result in the formation of prop-1-yne. This compound is treated withsodium amide and methyl idodie leading to the formation of but-2-yne. This is treated with hydrogen in the presence of Lindlar鈥檚 catalyst that forms an alkene. It is treated with osmium tetroxide and hydrogen peroxide. This will result in the formation of meso-butan-2,3-diol.The reaction is shown below.

12

(k) Synthesis of 2-methylhex-3-yn-2-ol

The acetylene is treated with sodium amide that will lead to the formation of a sodium salt. This salt is treated with bromoethane that result in the formation of but-1-yne. This is treated with sodium amide followed by treatement with sodium amide and acidification. This will form 2-methylhex-3-yn-2-ol.The reaction is shown below

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Most popular questions from this chapter

Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteine residues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione gives Gly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released. Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1282), followed by complete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenyl isothiocyanate does not give a recognizable phenylthiohydantoin, however.

(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normal product from Edman degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis?

(b) Oxidation of glutathione forms glutathione disulfide(GSSG). Propose a structure for glutathione disulfide, and write a balanced equation for the reaction of glutathione with hydrogen peroxide.

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan庐. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin庐 insecticide.

Acetals can serve as protecting groups for 1,2-diols,as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called as acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (鈥淓t鈥 is the abbreviation for ethyl.

In the presence of 18-crown-6, potassium permanganate dissolves inbenzene to give 鈥減urple benzene鈥 a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why dissolves in benzeneand why the reactivity of the permanganate ion is enhanced.

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