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    Alcohols Carbonyl

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    muhajireen
    The document discusses alcohols, aldehydes, and ketones. It provides information on the structures, properties, and reactions of ethanol, methanol, methanal, and other common alcohols, aldehydes, and ketones. It also describes the industrial production of methanol and its subsequent oxidation to methanal.

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    Alcohols Carbonyl

    Uploaded by

    muhajireen
    54 views8 pages
    The document discusses alcohols, aldehydes, and ketones. It provides information on the structures, properties, and reactions of ethanol, methanol, methanal, and other common alcohols, aldehydes, and ketones. It also describes the industrial production of methanol and its subsequent oxidation to methanal.

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    The document discusses alcohols, aldehydes, and ketones. It provides information on the structures, properties, and reactions of ethanol, methanol, methanal, and other common alcohols, aldehydes, and ketones. It also describes the industrial production of methanol and its subsequent oxidation to methanal.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    54 views8 pages

    Alcohols Carbonyl

    Uploaded by

    muhajireen
    The document discusses alcohols, aldehydes, and ketones. It provides information on the structures, properties, and reactions of ethanol, methanol, methanal, and other common alcohols, aldehydes, and ketones. It also describes the industrial production of methanol and its subsequent oxidation to methanal.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 8

    Alcohols, Aldehydes and Ketones From previous work you should be able to 1. State what a homologous series is.

    2. Understand what is meant by a functional group. 3. Understand the term oxidation in terms of gaining oxygen, loss of hydrogen and also loss of electrons. 4. Understand the term alcohol. 5. Know about and give the equation for the production of ethanol from glucose using the enzyme zymase found in yeast. Common alcohol 6.1

    Common alcohol is an organic compound called ethanol. Ethanol is the alcohol, which is present in all drinks. In can safely be consumed in small doses but in large amounts can cause drunkenness and disease of the liver (cirrhosis). Ethanol is an important chemical in industry and is just one of a homologous series of compounds called alcohols ( CnH2n+1OH) Properties of Ethanol Property Appearance Solubility pH Conduction Burning Structure of Ethanol H H | | H-C-C-O-H | | H H Result Alkanes methane CH4 ethane propane butane pentane Names of alcohols Alcohols methanol CH3OH

    functional group

    The O - H group is called the hydroxyl group. Do not confuse with the hydroxide ion. alcohols do not break up to give ions.

    Burning ethanol

    to pump

    Results The cobalt chloride paper turns blue to pink. This shows water has been formed. Ethanol must contain hydrogen; oxygen can be obtained from the air The limewater turns cloudy. This shows that carbon dioxide has been formed. Ethanol must contain carbon; the oxygen can be obtained from the air C2H5OH + 3 O2 => 2 CO2 + 3 H2O

    cobalt chloride paper

    lime water

    Conclusion Ethanol must contain both carbon and hydrogen.

    Industrial Ethanol

    6.2

    The fermentation of carbohydrate has provided a source of ethanol for thousands of years mainly in the form of alcoholic drinks. However the industrial use of ethanol has greatly increased over recent years.

    Manufacture of ethanol
    1. From fermentation C6H12O6 => C2H5OH + CO2

    2. Industrial preparation from crude oil Cracking produces ethene. which can be hydrated using a catalyst to produce ethanol C2H4 + H2O => C2H5OH

    Uses of Ethanol stain removers


    thermometers

    Ethanol

    wines, beers and spirits

    Feedstock

    Fuel for cars and spirit burners

    vinegar

    ether

    chloroform

    ethyl esters

    solvents in varnishes, dyes, perfumes anddrugs

    Ethanol as a feedstock
    Ethanol can be used to prepare ethene, which could be important, when fossil fuel run out as ethene is important in the plastics industry.
    aluminum oxide (in ceramic wool) ethene

    Clip
    Dehydration Reaction
    C2H5OH => C2H4 + H2 O

    ceramic wool soaked in ethanol

    The ethanol loses a molecule of water

    Alcohols

    6.3

    Alcohols exist as a homologous series with the general formula CnH2n+1OH. This means that all the alcohols will have similar chemical properties and gradually increasing physical properties Like hydrocarbons alcohols show isomerism i.e. same molecular formula and different structures Alcohol methanol Molecular formula CH3OH Structural formula H | H-C-O-H | H H H | | H-C-C- O-H | | H H H H H | | | H-C-C-C-O-H | | | H H H B.Pt [oC] Example of isomers -

    65

    ethanol

    C2H5OH |

    79

    H H | | H-C-O-C-H | | H H

    An isomer but not an alcohol as no hydroxyl group is present

    propanol

    C3H7OH

    97

    H | Only alcohol H O H isomers required | | | H-C-C-C-H | | | H H H propan - 2 - ol H | H O H | | | H-C-C-C-H | | | H C H /|\ HHH 2- methylpropan-2-ol

    butanol

    C4H9OH

    117

    pentanol

    C5H11OH

    Alcohol Structures

    6.4

    Although all alcohols have similar chemical properties, there are some differences depending upon the detailed structure of the alcohol, especially the position of the hydroxyl group. In addition to straight and branched chains there are also rings and aromatic alcohols as well as alcohols with more than one hydroxyl group. Primary [1o], Secondary [2o] and Teriary [3o] alcohols Primary [1o] H H H | | | H-C-C-C-O-H | | | H H H

    In 1o alcohols the carbon joined to the hydroxyl group is also joined to two other hydrogens and one carbon

    Secondary [2o]

    H | H O H | | | H-C-C-C-H | | | H H H H | H O H H | | | | H-C-C-C-C-H | | | | H C H H /|\ HHH

    In 2o alcohols the carbon joined to the hydroxyl group is also joined to one other hydrogen and two carbons

    Teriary [3o]

    In 3o alcohols the carbon joined to the hydroxyl group is also joined to three other carbons and no hydrogens

    3 isomers of C5H11OH

    Cyclohexanol

    Dihydric annd trihydric alcohols

    ethane-1,2-diol

    propane-1,2,3-triol

    Oxidising Alcohols

    6.5

    The combustion reactions of alcohols are examples of oxidation since the molecules react with oxygen. However milder oxidation can affect only the functional group. Oxidation of alcohol depends upon whether the alcohol is 1o; 2o or 3o. O-H | R - C - H + [O] | H -H2O => R - C = O | H an aldehyde H O-H | | H - C - C - H + [O] | | H H ethanol -H2O H | => H - C - C = O | | H H ethanal + [O] => R-C=O | O-H carboxylic acid H + [O] | => H - C - C = O | | H O-H ethanoic acid

    1o

    2o O-H | R - C - H + [O] | R* -H2O => R - C = O+ | R* a ketone H O-H | | H - C - C - H + [O] | | H C /|\ HHH propanan - 2 - ol 3o O-H | R1 - C - R3 | R2 HHH \|/ C | -C- O-H | C /|\ HHH -H2O H | H-C -C=O | | H C /|\ HHH propanone [O] => no further oxidation

    =>

    [O]

    => no further oxidation

    + [O]

    =>

    no oxidation

    H | H-C | H

    + [O]

    =>

    no oxidation

    2 methylpropan - 2- ol

    Aldehydes and ketones


    Both aldehydes and ketones contain the carbonyl group C = O.

    6.6

    Aldehydes Theseare carbon compounds which contain a carbonyl group at the end of a chain of carbon atoms. i.e. They contain the -CHO functional group. Aldehydes are also called alkanals, a homologous series with general formula CnH2nO. Aldehyde methanal Formula showing functional group HCHO Structural formula H | H-C =O

    ethanal

    CH3CHO

    H H | | H-C -C =O | H

    propanal

    C2H5CHO

    Ketones These are compounds which contain a carbonyl group, in the middle of a chain of carbon atoms i.e. they contain the - CO Ketones are also called alkanones forming their own homologous series with the general formula CnH2nO.[same as aldehydes] Ketone Formula showing functional group CH3COCH3 Structural formula

    propanone

    H O H | || | H-C -C-C -H | | H H H O H H | || | | H-C -C-C- C -H | | | H H H

    butanone

    C2H5COCH3

    pentan -3 - one

    C2H5COC2H5 +

    pentan -2 - one

    CH3COC3H7

    Oxidation of alderhydes An important difference between aldehydes and ketones is that aldehydes are readily oxised, ketones are not. Several oxidising agents may be used Copper(II) oxide copper(II) oxide wrapped in ceramic wool

    pH paper turns orange

    ceramic wool soaked in ethanol

    C2H5OH => CH3CHO => CH3COOH

    Oxidising agents to differentiate between aldehydes and ketones Oxidising agent acidified potassium dichromate solution Benedicts reagent Obsevations orange => blue/green blue => orange/green Explaqnation Cr2 O7 2- => Cr3+ Cu2+ => Cu+

    Tollens reagent

    colourless => silver mirror

    Ag+ => Ag

    Methanol and methanal

    6.7

    About 50 million tonnes of methanol is manufactured each year, 50% of this is oxidised to methanal. Both of these are used mainly as feedstocks for making a variety of products including drugs and plastics. 1. Synthesis gas This is a mixture of carbon monoixide and hydrogen, it can be made from the reaction of water with either methane or coal. The reaction is called steam reforming.

    12000C

    H 2O H 2O

    =>
    900oC

    CO CO

    + +

    H2 3 H2

    CH4 +
    2. Manufacturing methanol

    =>
    Ni cat. 30 atmos.

    Synthesis gas can be changed into methanol, the ration of CO and H2 is altered and reacted ZnO/Cr2O3 cat

    CO
    OR

    2 H2

    =>
    300oC 300 atmos. CuO/ZnO/Al2O3 cat.

    CH3OH

    CO

    2 H2

    =>
    200oC 60 atmos.

    CH3OH

    3.Manufacturing methanal Methanol can be oxidised to methanal by using oxygen from the air. Ag cat.

    CH3OH

    1/2 O2

    =>
    600oC

    HCHO

    H2O

    Using methanol and methanal


    Methanol Gasoline Silicones Fabrics Drugs Plastics Methanal Formalin Adhesives Plastics Explosives Antiseptics

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