Predict the products obtained from the reaction of oleic acid with the following reagents.

  1. NaOH in water
  2. H2and a nickel catalyst
  3. Br2 in CCl4
  4. Ozone, then dimethyl sulfide
  5. Warm KmnO4in water
  6. CH2I2/ Zn(Cu)

Short Answer

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Step by step solution

01

Step-1. Explanation of part (a):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. It is solvable in an aqueous base to produce soaps called oleates.

02

Step-2. Explanation of part (b):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. The hydrogenations of double bond yield the saturated derivative, that is, stearic acid.

03

Step-3. Explanation of part (c):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. Bromination reaction occurs at the double bond. Firstly, the bromonium ion forms, then bromide ion acts as a nucleophile and attacks at the carbon from the opposite plane to that of bromonium ion due to which bromonium ion ring opens and both bromines are formed anti to each other.

04

Step-4. Explanation of part (d):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. Ozonolysis of oleic acid is an essential route to azelaic acid formation.

05

Step-5. Explanation of part (e):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. On reaction with potassium permanganate and water, oxidation occurs at the double bond and carboxylic group gets attached to both the ends of double bond giving the products as shown.

06

Step-6. Explanation of part (f):

Oleic acid is the most common fatty acid in nature. It is classified as monounsaturated omega-9 fatty acid and it is a solid with low melting point. It is a long chain carboxylic acid. Oleic acid occurs in fats, the phospholipids that make membranes, cholesterol esters etc. Double bond present in oleic acid undergoes Simmons-Smith reaction and formation of cyclopropane occurs at the double bond.

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Most popular questions from this chapter

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.

Show how you would accomplish the following multistep syntheses using the indicated starting material and any necessary reagents.

(a) hept-6-en-1-ol caprolactone

(b) methoxybenzenep-methoxybenzamide

(c)

(d)

Gallic acid Mescaline

An enolate is a very strong nucleophile. Bromine is a strong electrophile, so it can react with much weaker nucleophiles. Give mechanisms for the reactions of bromine with cyclopentene and with phenol, which are both much weaker nucleophiles than an enolate.

Question: Arrange each group of compounds in order of increasing acidity.

  1. phenol, ethanol, acetic acid
  2. p-toluenesulfonic acid, acetic acid, chloroacetic acid
  3. benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
  4. butyric acid, α-bromobutyric acid, β-bromobutyric acid

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.

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