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:

alcohols converted into good leaving groups

 

 

 

 

Section 9.1B:

Williamson ether synthesis

alkyl halide must be methyl or primary to avoid competing elimination

 

 

Section 11.4B:

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

deprotect with aqueous acid

 

Section 12.2D:

 

   

activates carboxylic acids

 

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

adds acetyl group to acohols, amines

 

 

Section 13.6A

goes through enamine intermediate

 

haloform reaction – also works with Br₂, I₂

 

 

Section 13.6B

Wittig reaction

 

Section 13.6C

 

 

Section 13.6D

Grignard reagent – carbon nucleophile

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

Can also use R-Cl

 

 

 

Grignards add to esters, acid chlorides twice

 

organolithium – similar to Grignard

 

Gilman reagent

 

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

 

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

 

Section 14.2B

nucleophilic aromatic substitution

 

Section 14.3A

Hoffman elimination - least  substituted alkene produced

 

Cope elimination

 

 

Section 15.2B

 

Section 15.2D

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

 

 

 

 

method to protect alcohol – remove with H₃O⁺

 

another alcohol protecting group: remove with F^- ion

 

Section 15.6A:

watch out for the possibility of carbocation rearrangements!

 

 

watch out for the possibility of carbocation rearrangements!

 

 

ortho-para directing vs. meta-directing groups

 

Section 15.7A:

Markovnikov addition of water without possibility of carbocation shifting

 

Section 15.7C:

pinacol rearrangement

Hoffman rearrangement

 

Section 15.10:

Diels-Alder: cis/trans stereoselectivity

 

bicyclic Diels-Alder product - no stereoselectivity

 

 

Cope rearrangement

 

Claisen rearrangement

 

Section 16.11B:

 

 

Section 16.13A:

reduces aldehydes/ketones, but not carboxylic acid derivatives

 

reduces aldehydes, ketones, carboxylic acid derivatives

 

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

 

Section 16.13B:

 

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

 

alkyne to cis-alkene

 

alkyne to trans-alkene

 

 

Section 16.13C:

 

Section 16.13D:

primary alcohol to acid

 

secondary alcohol to ketone

oxidation at the benzylic position

 

Swern oxidation

 

abbreviated PCC

 

 

 

cis diols cleaved, not trans

 

 

KMnO₄ also oxidizes primary alcohols and aldehydes to acids

 

Section 17.2B:

radical halogenation is regiospecific – depends on stablity of radical intermediate

NBS can be source of Br in radical halogenation reactions

regiospecificity: benzylic / allylic