Give an equation for the complete hydrogenation of trilinolein using an excess of hydrogen. Name the product and predict approximate melting points for the starting material and the product.

Short Answer

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Hydrogenation is a chemical reaction between molecular hydrogen and another compound or element usually in the presence of a catalyst such as nickel, palladium, or platinum. This type of reaction is an example of alkene addition, and two hydrogen atoms are added across the double bond of an alkene which results in formation of a saturated alkane.

Step by step solution

01

Step-1. Hydrogenation reaction:

Hydrogenation is a chemical reaction between molecular hydrogen and another compound or element usually in the presence of a catalyst such as nickel, palladium, or platinum. This type of reaction is an example of alkene addition, and two hydrogen atoms are added across the double bond of an alkene which results in formation of a saturated alkane.

02

Step-2. Hydrogenation of trilinolein:

Trilinolein on hydrogenation with excess hydrogen in presence of nickel catalyst results in the formation of tristearin which is solid at room temperature. Melting point of trilinolein is less than -40C and it is liquid at room temperature. Melting point of tristearin is 720C. Melting point of trilinolein is lower than triolein because more double bonds lower the melting point. Sources differ on the melting point of trilinolein, ranging from -170C to -430C.

Hydrogenation of trilinolein

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Most popular questions from this chapter

Phospholipids undergo saponification much like triglycerides. Draw the structure of a phospholipid meeting the following criteria. Then draw the products that would result from its saponification.

(a) a cephalin containing stearic acid and oleic acid

(b) a lecithin containing palmitic acid.

When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formula C18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warm potassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. The NMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure for petroselenic acid, and show how your structure is consistent with these observations.

Question: Trimyristin, a solid fat present in nutmeg, is hydrolyzed to give one equivalent of glyceroland three equivalents of myristic acid. Give the structure of trimyristin.

Show how you would convert linoleic acid to the following fatty acid derivatives.

  1. Octadecane-1-ol
  2. Stearic acid
  3. Octadecyl stearate
  4. Nonanal
  5. Nonanedioic acid
  6. 9,10,12,13-tetrabromostearic acid

Draw the structure of an optically active triglyceride containing one equivalent of stearic acid and two equivalents of oleic acid. Draw the products expected when this triglyceride reacts with the following reagents. In each case, predict whether the products will be optically active.

  1. H2and a nickel catalyst
  2. Br2inCCl4
  3. Hot aqueousNaOH
  4. Ozone followed by (CH3)2S
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