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    Protecting Groups Alcohols and Aldehydes

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    Nickson
    The document discusses protecting groups for alcohols and aldehydes. It outlines the criteria for a protecting group which includes being easy to add and remove while making the functional group resistant to unwanted reactions. Common protecting groups for alcohols mentioned are benzyl ethers, silyl ethers, acetals, esters, and MEM groups. Acetals are discussed as protecting groups for aldehydes. The summary table lists representative protecting groups for alcohols and aldehydes along with how they are added and removed, what chemical transformations they resist, and what they are susceptible to.

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    Protecting Groups Alcohols and Aldehydes

    Uploaded by

    Nickson
    49 views18 pages
    The document discusses protecting groups for alcohols and aldehydes. It outlines the criteria for a protecting group which includes being easy to add and remove while making the functional group resistant to unwanted reactions. Common protecting groups for alcohols mentioned are benzyl ethers, silyl ethers, acetals, esters, and MEM groups. Acetals are discussed as protecting groups for aldehydes. The summary table lists representative protecting groups for alcohols and aldehydes along with how they are added and removed, what chemical transformations they resist, and what they are susceptible to.

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    protecting groups alcohols and aldehydes

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    The document discusses protecting groups for alcohols and aldehydes. It outlines the criteria for a protecting group which includes being easy to add and remove while making the functional group resistant to unwanted reactions. Common protecting groups for alcohols mentioned are benzyl ethers, silyl ethers, acetals, esters, and MEM groups. Acetals are discussed as protecting groups for aldehydes. The summary table lists representative protecting groups for alcohols and aldehydes along with how they are added and removed, what chemical transformations they resist, and what they are susceptible to.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    49 views18 pages

    Protecting Groups Alcohols and Aldehydes

    Uploaded by

    Nickson
    The document discusses protecting groups for alcohols and aldehydes. It outlines the criteria for a protecting group which includes being easy to add and remove while making the functional group resistant to unwanted reactions. Common protecting groups for alcohols mentioned are benzyl ethers, silyl ethers, acetals, esters, and MEM groups. Acetals are discussed as protecting groups for aldehydes. The summary table lists representative protecting groups for alcohols and aldehydes along with how they are added and removed, what chemical transformations they resist, and what they are susceptible to.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 18

    PCH3504CM

    Organic synthetic methods


    Topic : Protecting group:alcohols –aldehydes 

    Unit : 3 (Retrosynthesis ll)

    Done by, Infantia Mirin N(21PCHE04)


    Table of contents
    Introduction
    Criteria for a protecting group
    Importance of protecting group
    Protecting groups for alcohols
    Protecting groups for aldehydes
    Summary
    Introduction
    Protection and deprotection is an important part of organic synthesis. During the
    course of synthesis, we many times desire to perform reaction at only one of the
    two functional groups in any single organic molecules.
    For example, in an organic compound possessing two functional groups like ester
    and ketone, we have to perform reaction at only ester group, them the keto group
    needs to be protected.
    Example:
    Criteria for a protecting group:
    (i) It must be easy to put in
    (ii) It must be resistant to reagents that would attack the unprotected function
    group.
    (iii) It must be easily removed.
    Importance of protecting group :
    Using a protecting group in the reaction gives us useful and desired product which
    we needed.
    The usual way of reacting a less reactive group in presence of a more reactive
    group can be done with the help of protecting groups.
    Let us see about protecting groups for alcohols and aldehydes.
    Protecting groups for alcohols:
    Alcohols can be protected by benzylic ethers and can be easily deprotected to give the
    desired product.

    1 on reaction with benzyl chloride in presence of base gives the alcohol protected as
    benzylic ether 2. We can do reactions on this protected alcohol and deprotection can
    be done by simple hydrogenation in presence of catalyst.
    Silyl ethers as protecting groups for alcohols:

    This silyl ether can be removed by reaction with an aqueous acid or the fluoride
    ion.
    Acetals as protecting groups for alcohols:
    Cis 1,2 - diols and cis or trans 1,3 diols can be protected as cyclic acetals or
    ketals.
    Esters as protecting groups for alcohols:
    Esters are more widely used as protecting groups for acids. Normal esters can be
    hydrolyzed in aqueous acid or base under fairly vigorous conditions.
    MEM as protecting groups for alcohols
    It is similar to MOM ethers in their stability to protic acids.
    Protecting groups for phenols:
    MeI, potassium carbonate, acetone reflux for 6 hours. This is a very common and
    often efficient method for the preparation of phenolic methyl ethers. This method is
    also applicable for formation of phenolic benzyl ethers.
    Protecting groups for aldehydes:
    Acetals as protecting groups:
    General mechanism:
    Summary:

    Group Protecting To add To remove PG resists PG reacts with


    group

    Aldehydes Acetal Alcohol in Acid hydrolysis Nucleophiles, Electrophiles,


    presence of baes, reducing Oxidizing
    acid medium agents agents.

    Alcohols Ethers Benzyl Catalytic Electrophiles HX


    chloride, base hydrogenation
    Acid hydrolysis
    Acetals ZnBr2 Bases Acids

    MEM Bases Acids


    Summary

    Group Protecting To add To remove PG resists PG reacts with


    group

    Alcohols Esters RCOCl, Ammonia, Electrophiles Nucleophiles


    pyridine methanol

    Phenols Ethers Dimethyl HI Bases Attack by


    sulphate, electrophiles
    potassium on the ring
    carbonate

    Acetal MeOCH2Cl, Acetic acid, Bases Attack by


    base water electrophiles
    on the ring
    CSIR question:
    Reference:
    Stuart Warren, Paul Wyatt, (2008). Organic Synthesis: The Disconnection
    Approach, (2nd ed.)
    Jonathan Clayden, Nick Greeves, Stuart Warren, (2012). Organic Chemistry, (2nd
    ed.), New York
    Theodera. W. Greene, Peter. G. M. Wuts, protective groups in organic synthesis
    (4th ed).

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