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Appendix: Review of laboratory synthesis reactions

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    1125
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    While the focus of this textbook is on organic reactions occuring in living cells, if you are a chemistry major, or are planning to take a standardized exam such as the MCAT, you will need to be familiar with a number of laboratory synthesis reactions. Here, we review the lab synthesis reactions covered in this text, which include most of the reactions typically covered in traditional organic texts. Click on the chapter/section number for direct links to the section where these reactions are introduced.

    Section 8.5B:

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    alcohols converted into good leaving groups

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    Section 9.1B:

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    Williamson ether synthesis

    alkyl halide must be methyl or primary to avoid competing elimination

    Section 11.4B:

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    cyclic acetal ‘protects’ ketone/aldehyde group – stable to bases/nucleophiles

    deprotect with aqueous acid

    Section 12.2D:

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    activates carboxylic acids

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    acetic anhydride is a good acetyl group donor (activated acetic acid)

    adds acetyl group to acohols, amines

    Section 13.6A

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    goes through enamine intermediate

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    haloform reaction – also works with Br2, I2

    Section 13.6B

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    Wittig reaction

    Section 13.6C

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    Section 13.6D

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    Grignard reagent – carbon nucleophile

    No acidic protons can be present (it’s a strong base)

    Can also use R-Cl

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    Grignards add to esters, acid chlorides twice

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    organolithium – similar to Grignard

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    Gilman reagent

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    Gilman reagent will react with alkyl, vinyl halides as well as carbonyls

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    Gilman reagent will add once to acid chlorides to make a ketone

    Section 14.2B

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    nucleophilic aromatic substitution

    Section 14.3A

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    Hoffman elimination - least substituted alkene produced

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    Cope elimination

    Section 15.2B

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    Section 15.2D

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    anti-Markovnikov addition of water to alkene. Notice syn addition!

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    method to protect alcohol – remove with H3O+

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    another alcohol protecting group: remove with F- ion

    Section 15.6A:

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    watch out for the possibility of carbocation rearrangements!

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    watch out for the possibility of carbocation rearrangements!

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    ortho-para directing vs. meta-directing groups

    Section 15.7A:

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    Markovnikov addition of water without possibility of carbocation shifting

    Section 15.7C:

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    pinacol rearrangement

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    Hoffman rearrangement

    Section 15.10:

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    Diels-Alder: cis/trans stereoselectivity

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    bicyclic Diels-Alder product - no stereoselectivity

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    Cope rearrangement

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    Claisen rearrangement

    Section 16.11B:

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    Section 16.13A:

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    reduces aldehydes/ketones, but not carboxylic acid derivatives

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    reduces aldehydes, ketones, carboxylic acid derivatives

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    can reduce ester/amide to aldehyde (LiAlH4 can't do this)

    Section 16.13B:

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    alkynes, aldehyde, ketones, nitro groups also reduced by H2/Pt (but not acid derivatives!)

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    alkyne to cis-alkene

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    alkyne to trans-alkene

    Section 16.13C:

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    Section 16.13D:

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    primary alcohol to acid

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    secondary alcohol to ketone

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    oxidation at the benzylic position

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    Swern oxidation

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    abbreviated PCC

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    cis diols cleaved, not trans

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    KMnO4 also oxidizes primary alcohols and aldehydes to acids

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    Section 17.2B:

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    radical halogenation is regiospecific – depends on stablity of radical intermediate

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    NBS can be source of Br in radical halogenation reactions

    regiospecificity: benzylic / allylic

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