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ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > Organic Chemistry With a Biological Emphasis > Appendix: Review of laboratory synthesis reactions

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Appendix: Review of laboratory synthesis reactions

Table of Contents

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:

image002.png

alcohols converted into good leaving groups

 

 

image004.png

image006.png

 

 

Section 9.1B:

image008.png

Williamson ether synthesis

alkyl halide must be methyl or primary to avoid competing elimination

 

 

Section 11.4B:

image010.png

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

deprotect with aqueous acid

 

Section 12.2D:

 

  image012.png 

activates carboxylic acids

 

image014.png

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

adds acetyl group to acohols, amines

 

 

Section 13.6A

image016.png

goes through enamine intermediate

 

image018.png

haloform reaction – also works with Br2, I2

 

 

Section 13.6B

image020.png

Wittig reaction

 

Section 13.6C

image022.png

 

 

Section 13.6D

image024.png

Grignard reagent – carbon nucleophile

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

Can also use R-Cl

 

image026.png

 

image028.png

 

image030.png

Grignards add to esters, acid chlorides twice

 

image032.png

organolithium – similar to Grignard

 

image034.png

Gilman reagent

 

image036.png

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

 

image038.png

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

 

Section 14.2B

image040.png

nucleophilic aromatic substitution

 

Section 14.3A

image042.png

Hoffman elimination - least  substituted alkene produced

 

image044.png

Cope elimination

 

 

Section 15.2B

image046.png

image048.png

 

Section 15.2D

image050.png

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

 

image052.png

 

image054.png

 

image056.png

 

image058.png

method to protect alcohol – remove with H3O+

 

image060.png

another alcohol protecting group: remove with F- ion

 

Section 15.6A:

image062.png

watch out for the possibility of carbocation rearrangements!

 

image064.png

 

image066.png

watch out for the possibility of carbocation rearrangements!

 

image068.png

 

image070.png

ortho-para directing vs. meta-directing groups

 

Section 15.7A:

image072.png

Markovnikov addition of water without possibility of carbocation shifting

 

Section 15.7C:

image074.png

pinacol rearrangement

image076.png

Hoffman rearrangement

 

Section 15.10:

image078.png

Diels-Alder: cis/trans stereoselectivity

 

image080.png

bicyclic Diels-Alder product - no stereoselectivity

 

image082.png

 

image084.png

Cope rearrangement

 

image086.png

Claisen rearrangement

 

Section 16.11B:

image088.png

 

image090.png

 

Section 16.13A:

image092.png

reduces aldehydes/ketones, but not carboxylic acid derivatives

 

image094.png

reduces aldehydes, ketones, carboxylic acid derivatives

 

image096.png

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

 

Section 16.13B:

image098.png

 

image100.png

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

 

image102.png

alkyne to cis-alkene

 

image104.png

alkyne to trans-alkene

 

 

Section 16.13C:

image106.png

image108.png

 

Section 16.13D:

image110.png

primary alcohol to acid

 

image112.png

secondary alcohol to ketone

image114.png

oxidation at the benzylic position

 

image116.png

Swern oxidation

 

image118.png

abbreviated PCC

 

image120.png

image122.png

 

 

image124.png

cis diols cleaved, not trans

 

image126.png

image128.png

 

image130.png

KMnO4 also oxidizes primary alcohols and aldehydes to acids

image132.png

 

Section 17.2B:

image134.png

radical halogenation is regiospecific – depends on stablity of radical intermediate

image136.png

image138.png

NBS can be source of Br in radical halogenation reactions

regiospecificity: benzylic / allylic

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