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Chapter 20: Q19P (page 1038)

Some of the earliest synthetic detergents were the sodium alkyl sulfates, CH3(CH2)nCH2-OSO3-Na+ .Show how you would make sodium octadecylsulfate using tristearin as your organic starting material.

Short Answer

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Formation of sodium octadecylsulfate

Step by step solution

01

Step-1. Reduction of tristearin to octadecyl alcohol:

Tristearin on reaction with lithium aluminiumhydride undergoes reduction and gets converted to octadecyl alcohol and glycerol. Lithium aluminium hydride acts as a reducing agent and overall, 3 molecules of octadecyl alcohol and one molecule of glycerol is formed.

02

Step-2. Conversion of octadecyl alcohol to sodium octadecylsulfate:

Octadecyl alcohol undergoes sulfonation under cold conditions and gets converted to octadecyl sulfonic acid which on reaction with base such as sodium hydroxide forms sodium octadecylsulfate.

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Most popular questions from this chapter

The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

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®. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin® insecticide.

Show how you would use an acid chloride as an intermediate to synthesize(a) N-phenylbenzamide (PhCONHPh)from benzoic acid and aniline.(b) phenyl propionate(CH3CH2COOPh) from propionic acid and phenol.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-bromobut-2-ene→trans-pent-3-enoic acid (two ways)

(b)hex-3-ene→propanoic acid

(c) but-2-enal→but-2-enoic acid

(d) hexanoic acid→hexanal

(e)

(f)

(g)

(h)
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