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    Assignment 1 Organic Chemistry

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    Anotidaishe Mugadza
    1) Hydrogen bonds form between electron-rich donor atoms like oxygen and hydrogen atoms bonded to more electronegative atoms. Water has a higher boiling point than hydrogen sulfide due to stronger hydrogen bonding between water molecules. 2) Addition of HBr to propene yields different products depending on presence of benzoyl peroxide. Without it, 2-bromopropane forms via a carbocation intermediate. With it, a free radical mechanism forms 1-bromopropane as the major product. 3) Methanol can be converted to ethanol via multiple steps including a Wurtz reaction and chlorination/hydrolysis. Ethanol can be converted to methanol through oxidation, hydrolysis,

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    Assignment 1 Organic Chemistry

    Uploaded by

    Anotidaishe Mugadza
    67 views9 pages
    1) Hydrogen bonds form between electron-rich donor atoms like oxygen and hydrogen atoms bonded to more electronegative atoms. Water has a higher boiling point than hydrogen sulfide due to stronger hydrogen bonding between water molecules. 2) Addition of HBr to propene yields different products depending on presence of benzoyl peroxide. Without it, 2-bromopropane forms via a carbocation intermediate. With it, a free radical mechanism forms 1-bromopropane as the major product. 3) Methanol can be converted to ethanol via multiple steps including a Wurtz reaction and chlorination/hydrolysis. Ethanol can be converted to methanol through oxidation, hydrolysis,

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    1) Hydrogen bonds form between electron-rich donor atoms like oxygen and hydrogen atoms bonded to more electronegative atoms. Water has a higher boiling point than hydrogen sulfide due to stronger hydrogen bonding between water molecules. 2) Addition of HBr to propene yields different products depending on presence of benzoyl peroxide. Without it, 2-bromopropane forms via a carbocation intermediate. With it, a free radical mechanism forms 1-bromopropane as the major product. 3) Methanol can be converted to ethanol via multiple steps including a Wurtz reaction and chlorination/hydrolysis. Ethanol can be converted to methanol through oxidation, hydrolysis,

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    67 views9 pages

    Assignment 1 Organic Chemistry

    Uploaded by

    Anotidaishe Mugadza
    1) Hydrogen bonds form between electron-rich donor atoms like oxygen and hydrogen atoms bonded to more electronegative atoms. Water has a higher boiling point than hydrogen sulfide due to stronger hydrogen bonding between water molecules. 2) Addition of HBr to propene yields different products depending on presence of benzoyl peroxide. Without it, 2-bromopropane forms via a carbocation intermediate. With it, a free radical mechanism forms 1-bromopropane as the major product. 3) Methanol can be converted to ethanol via multiple steps including a Wurtz reaction and chlorination/hydrolysis. Ethanol can be converted to methanol through oxidation, hydrolysis,

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    TEXILA AMERICAN UNIVERSITY

    COLLEGE OF MEDICINE
    NAME: TINOTENDAISHE MUGADZA
    STUDENT NUMBER: 34558
    PROGRAM: ORGANIC CHEMISTRY
    TITLE ASSIGNMENT 1
    LECTURER DR SYLVESTER
    DUE DATE 28 July 2020
    1. What are hydrogen bonds? What type of compounds forms hydrogen bond? How does its
    strength compare with other types of bonds? Explain why water boils at 100 0C where as
    Hydrogen sulphide (H2S) boils at －62 0C. (10)

    A hydrogen bond is a partial intermolecular bonding interaction between a lone pair on an


    electron rich donor atom, particularly the second-row elements nitrogen (N), oxygen (O), or
    fluorine (F), and the antibonding molecular orbital of a bond between hydrogen (H) and a more
    electronegative atom or group. Hydrogen bonds are significantly strong but not as strong as
    covalent and ionic bonds. Water has a higher boiling point than hydrogen sulphide. The
    intermolecular attractions between water molecules are stronger than H2S molecules due to
    hydrogen bonding in H2O due to high electronegativity and small size of oxygen atom.

    2. Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide,
    the same reaction yields 1-bromopropane. Explain and give mechanism. (10)

    Addition of HBr to propene is an example of an electrophilic substitution


    reaction. Hydrogen bromide provides an electrophile, H+H+. This electrophile
    attacks the double bond to form 1∘1∘ and 2∘2∘ carbocations as shown:

    Secondary carbocations are more stable than primary carbocations. Hence,


    the former predominates since it will form at a faster rate. Thus, in the next
    step, Br– attacks the carbocation to form 2 – bromopropane as the major
    product
    This reaction follows Markovnikov’s rule where the negative part of the
    addendum is attached to the carbon atom having a lesser number of hydrogen
    atoms.In the presence of benzoyl peroxide, an addition reaction takes place
    anti to Markovnikov’s rule. The reaction follows a free radical chain
    mechanism as:
    Secondary free radicals are more stable than primary radicals. Hence, the
    former predominates since it forms at a faster rate. Thus, 1 – bromopropane is
    obtained as the major product.
    In the presence of peroxide, Br free radical acts as an electrophile. Hence, two
    different products are obtained on addition of HBr to propene in the absence
    and presence of peroxide.

    3. How would you convert: Methanol in to ethanol and vice-versa. A primary alcohol in to
    secondary and tertiary alcohols. (10)

    There are various ways to turn methanol into ethanol


     In order to increase the carbon number, we proceed through the Wurtz reaction. Simply, react
    the methanol with one mole of HCl to get chloromethane.
     Now two moles of chloromethane react with each other in presence of 2 moles of Sodium in a
    medium of dry ether. (Wurtz reaction). The reaction gives us one mole of ethane as product.
     Now react the ethane molecule with Cl2 gas in presence of sunlight in a controlled chlorination
    environment. This will give a molecule of chloroethane (substitution reaction).
     Now this could be turned into ethanol by reacting it with aqueous solution of alkali hydroxide.

    To turn ethanol into methanol

    One easier way would be to heat Ethanol in acid environment, conduct an ozonolysis and then
    catalyze with zinc:

    CH3CH2OH+H2SO4 = CH2=CH2

    CH2=CH2 -> ozonolysis +Zn & H20 = 2HCHO

    HCH0+LiAlH4 = CH3OH

    Ethanol can also converted to methanol in the following series of steps:

    1.Ethanol first undergoes oxidation by reacting it with chromium trioxide to form acetic acid.

    CH₃CH₂OH +CrO₃ = CH₃COOH

    2. Acetic acid is then reacted with sodium hydroxide to form sodium acetate and water

    CH₃COOH +NaOH = CH₃COONa +H₂O

    3. In the third step the sodium acetate is reacted with sodium hydroxide and calcium oxide
    to form methane and sodium carbonate and calcium.

    CH₃COONa +NaOH + CaO = CH₄ + Na₂CO₃ + Ca

    4. Methane formed in step 3 is then reacted with chlorine molecule to form methyl chloride
    and hydrochloric acid

    CH₄ + Cl₂ =CH₃Cl + HCl

    5. In the last step methyl chloride is passed through aqueous potassium hydroxide to form
    methanol

    CH₃Cl + KOH = CH₃OH

    4. How is diethyl ether prepared from ethyl alcohol? Give the mechanism of the reactions.
    What happens when its reacts with (i) HI and (ii) Cl2 (10)
    Diethyl ether can be prepared both in laboratories and on an industrial scale by the
    acid ether synthesis.[10] Ethanol is mixed with a strong acid, typically sulfuric acid,
    H2SO4. The acid dissociates in the aqueous environment producing hydronium ions,
    H3O+. A hydrogen ion protonates the electronegative oxygen atom of the ethanol,
    giving the ethanol molecule a positive charge:

    CH3CH2OH + H3O+ → CH3CH2OH2+ + H2O

    A nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule


    from the protonated (electrophilic) ethanol molecule, producing water, a hydrogen
    ion and diethyl ether.

    CH3CH2OH2+ + CH3CH2OH → H2O + H+ + CH3CH2OCH2CH3

    This reaction must be carried out at temperatures lower than 150 °C in order to
    ensure that an elimination product (ethylene) is not a product of the reaction. At
    higher temperatures, ethanol will dehydrate to form ethylene. The reaction to make
    diethyl ether is reversible, so eventually an equilibrium between reactants and
    products is achieved. Getting a good yield of ether requires that ether be distilled
    out of the reaction mixture before it reverts to ethanol, taking advantage of Le
    Chatelier's principle.

    Another reaction that can be used for the preparation of ethers is the Williamson
    ether synthesis, in which an alkoxide (produced by dissolving an alkali metal in the
    alcohol to be used) performs a nucleophilic substitution upon an alkyl halide.[

    An acid‐catalyzed cleavage that occurs when hydriodic acid (HI) mixes with ethers is
    the most significant reaction that ethers experience. This reaction proceeds via a
    nucleophilic substitution mechanism. Primary and secondary alkyl ethers react by an
    S N2 mechanism, while tertiary, benzylic, and alcylic ethers cleave by an S N1
    mechanism. A typical S N2 reaction would be the reaction of ethylisopropyl ether with
    HI. The mechanism for this reaction is:
    Notice that for S N2 substitution, the alkyl halide came from the less sterically
    hindered group. For S N1 type reactions, the alkyl halide forms from the fragment of
    the original molecule that forms the more stable cation. Thus, the reaction of t‐butyl
    ethyl ether with HI gives t‐butyl iodide and ethyl alcohol. The following mechanism
    occurs:

    Notice that if the original ionization of the t‐butyl ethyl ether formed a t‐butoxide
    ion and an ethyl carbocation, this would be a less stable arrangement. (Remember,
    the order of stability of carbocations is 3° > 2° > 1°.)

    The reaction of ether with halogens is known as halogenation of ether. The products
    we get when ethers react with halogens largely depend on the condition.

    For example, we get α,α'-dichlorodiethyl ether when diethyl ether reacts with
    Cl2 in dark.
    In presence of light and excess of chlorine, all the hydrogen atoms are replaced by
    chlorine.

    5. A) Compare the reactivity of Aldehydes and ketone in detail. (6). B) Explain the
    following naming reaction for the preparation of aldehyde with mechanism: Rosenmund
    reduction (2) Stephen reaction (2)

    Aldehydes are typically more reactive than ketones due to the following factors.

    1. Aldehydes are less hindered than ketones (a hydrogen atom is smaller than
    any other organic group).
    2. The carbonyl carbon in aldehydes generally has more partial positive charge
    than in ketones due to the electron-donating nature of alkyl groups.
    Aldehydes only have one e- donor group while ketones have two.

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