Draw the structure of an example of each of the following types of lipids:

(a) a saturated fat (b) a polyunsaturated oil (c) a wax (d) a soap (e) a detergent

(f) a phospholipid (g) a prostaglandin (h) a steroid (i) a sesquiterpene

Short Answer

Expert verified

a)

b)

c)

d)

e)

f)

g)

h)

i)

Step by step solution

01

(a)

Saturated fat: They are saturated with hydrogen atoms and no double bond is present.

Butyric acid has saturated short-chain fatty acid with a 4-carbon backbone, and one ketone and alcohol group.

02

(b)

Polyunsaturated oil: They have more than one unsaturated carbon bond (double/triple bonds). In linoleic acid, both alkene groups are cis and it has 18 carbon atoms with a carboxyl group in one hand.

03

(c)

Wax: It consists of long-chain fatty acid linked through ester oxygen to a long-chain alcohol.

Certylmyristate is an ester of cetyl alcohol and myristic acid.

04

(d)

Soap: Head composed of positively charged sodium ion, negatively charged oxygen ion with a fatty acid tail. Sodium stearate is a sodium salt of stearic acid. It contains a long hydrocarbon tail and a carboxylic acid head.

05

(e)

Detergent: Similar to soap with structure R-SO4¯,Na ion, R= long-chain alkyl group. Sodium dodecyl sulphate hashydrophobic 12-carbon chain and a polar sulfate head group.

06

(f)

Phospholipid: Two hydrophobic tail of fatty acid, one hydrophilic head joined together by alcohol or glycerol. Phosphatidylserine glutamate has two fatty acids attached in ester linkage to the first and second carbon of glycerol, and serine is attached through a phosphodiester linkage to the third carbon of glycerol.

07

(g)

Prostaglandin: Made up of unsaturated fatty acid, it contains cyclopentane ring. E1-Alprostadil has cyclopentane with two carbon chains—carboxyl group and hydroxyl group.

08

(h)

Steroid: 17 carbon atoms, bonded to four fused rings. Testosterone has 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-4-C-5.

09

(i)

Sesquiterpene: Consist of three isoprene units. β-bisaboleneAbisabolene is cyclohexene substituted by a methyl group at position 1, and a 6-methylhepta-1,5-dien-2-yl group at position 4.

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Most popular questions from this chapter

The synthesis of the alkylbenzenesulfonate detergent shown in figure 25-6 begins with the partial polymerization of propylene to give a pentamer.

Show how aromatic substitution reactions can convert this pentamer to the final synthetic detergent.

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.

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.

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

Oils containing highly unsaturated acids like linolenic acid undergo oxidation in air. This reaction, called oxidative rancidity, is accelerated by heat, explaining why saturated fats are preferred for deep fat frying.

(a) Molecular oxygen is a diradical. What type of mechanism does a diradical suggest for this reaction?

(b) Why is the position shown (carbon-11) a likely site for attack?

(c) Propose a plausible mechanism for this reaction.

(d) BHA and BHT are antioxidants added to foods to interrupt the oxidation mechanism. Suggest how these molecules might work as antioxidants.

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