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    Seminar 2

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    JJ Lim
    This document summarizes a seminar on organic chemistry that discusses β-carotene. β-Carotene is an orange pigment found in carrots and green vegetables. It is colored due to its long conjugated chain of alternating double bonds. When shaken with water, β-carotene and water form separate layers since β-carotene is nonpolar. When shaken with benzene, a homogeneous mixture forms since β-carotene is soluble in the nonpolar benzene. Bromine added to β-carotene turns colorless as the double bonds undergo electrophilic addition reactions. Acidified potassium manganate (VII) turned colorless when β-carotene was re

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    Seminar 2

    Uploaded by

    JJ Lim
    69 views2 pages
    This document summarizes a seminar on organic chemistry that discusses β-carotene. β-Carotene is an orange pigment found in carrots and green vegetables. It is colored due to its long conjugated chain of alternating double bonds. When shaken with water, β-carotene and water form separate layers since β-carotene is nonpolar. When shaken with benzene, a homogeneous mixture forms since β-carotene is soluble in the nonpolar benzene. Bromine added to β-carotene turns colorless as the double bonds undergo electrophilic addition reactions. Acidified potassium manganate (VII) turned colorless when β-carotene was re

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    B-carotene

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    SEMINAR 2

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    This document summarizes a seminar on organic chemistry that discusses β-carotene. β-Carotene is an orange pigment found in carrots and green vegetables. It is colored due to its long conjugated chain of alternating double bonds. When shaken with water, β-carotene and water form separate layers since β-carotene is nonpolar. When shaken with benzene, a homogeneous mixture forms since β-carotene is soluble in the nonpolar benzene. Bromine added to β-carotene turns colorless as the double bonds undergo electrophilic addition reactions. Acidified potassium manganate (VII) turned colorless when β-carotene was re

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    69 views2 pages

    Seminar 2

    Uploaded by

    JJ Lim
    This document summarizes a seminar on organic chemistry that discusses β-carotene. β-Carotene is an orange pigment found in carrots and green vegetables. It is colored due to its long conjugated chain of alternating double bonds. When shaken with water, β-carotene and water form separate layers since β-carotene is nonpolar. When shaken with benzene, a homogeneous mixture forms since β-carotene is soluble in the nonpolar benzene. Bromine added to β-carotene turns colorless as the double bonds undergo electrophilic addition reactions. Acidified potassium manganate (VII) turned colorless when β-carotene was re

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    © All Rights Reserved
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    of 2

    SEMINAR 2: ORGANIC CHEMISTRY Farah Mohamed Rasidi

    Answer all questions. (Date of discussion: 10 November 2017)

    Group Exercise:

    1. The diagram below shows the skeletal formula of β-carotene, which is an orangey
    yellow pigment found in carrots and leafy green vegetables. Many people take β-
    carotene as a dietary supplement because there is some evidence that high levels of β-
    carotene are associated with low incidences of cancer.

    a) Explain briefly why β-carotene is coloured.


    - β-carotene is orange coloured due to the long-conjugated chain of altering double bonds of
    the beta-carotene molecular structure.
    - The conjugated chain in carotenoids allows the absorption of green and blue part of the
    visible light spectrum, leaving red and yellow colours from the spectrum to be reflected back
    to the viewer.
    - Hence, the combination of red and yellow light reflected will cause the beta-carotene to
    appear orange colour.

    b) What is the functional group present in β-carotene?


    - β-carotene is composed of two retinyl groups

    c) What is the molecular formula and empirical formula of β-carotene?


    - Molecular formula: C40H56
    - Empirical formula: C5H7

    d) Explain what will happen when a few drops of β-carotene are shaken separately with
    distilled water and benzene.
    -When a few drops of β-carotene are shaken with distilled water, a two-layered mixture is
    formed because β-carotene is non-polar thus it is immiscible in water
    -When a few drops of β-carotene are shaken with benzene, a homogenous mixture is formed
    because β-carotene is non-polar soluble in organic compound benzene

    e) Predict and explain what will happen when a small amount of β-carotene is

    i. added to bromine and shaken.


    -Bromine added into β-carotene turns from brown to colourless as β-carotene
    undergoes electrophilic addition with bromine molecules.
    -As β-carotene contains 11 double bonds, these 11 double bonds have high
    electron densities thus they are susceptible to electrophilic attack.
    -11 bromine molecules are then polarized by 11 double bonds and the bromine
    atom in each bromine molecule that is closer to a double bond is partially
    positively charged, hence partial positively charged bromine atom will act as
    an electrophile to attack the double bond, binding bromine atom to a carbon
    atom with a (C-Br) bond and forming a carbocation intermediate that is
    electron deficient.
    -Positive bromide ion formed will then act as a nucleophile that attacks the
    carbocation intermediate, binding itself to the electron deficient carbon atom
    with a (C-Br) bond. As this goes on for the other 10 bromine molecules, all 22
    bromine atoms will bind to one β-carotene molecule.
    –Hence, the bromine molecules will eventually turn from brown to colourless.

    ii. refluxed with acidified potassium manganite (VII). –Acidified potassium


    manganite (VII) will turn from purple to colourless because β-carotene will
    undergo oxidation under reflux with acidified potassium manganite (VII), in
    which purple MnO4- ions are reduced to colourless Mn2+ ions.

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