substitution

PBr3 and SOCl2

PBr3 and SOCl2

March 20, 2015

Lately we’ve been talking a lot about converting alcohols to good leaving groups [halides] [tosylates and mesylates] You might think we’d be done already, but not yet! In today’s post we talk about a…

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Tosylates And Mesylates

Tosylates And Mesylates

March 10, 2015

Today we’re going to talk about a different way of making alcohols into good leaving groups – by turning them into tosylates and mesylates (“organosulfonates”). Here’s a brief summary o…

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Synthesis (3) – Reactions of Alkyl Halides

Synthesis (3) – Reactions of Alkyl Halides

January 10, 2014

In the last post, we began our discussion of synthesis by starting with the reactions of alkanes. Since we’ve learned only one important class of alkane reactions so far (free-radical halogenation), our “r…

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Guest Post On SN1/SN2/E1/E2 (6): Wrapup

Guest Post On SN1/SN2/E1/E2 (6): Wrapup

November 21, 2013

Part 6 of a 6 part series. Previous posts in the series:  1 2 3 4 5 – James  3 ½ Steps To Any SN1/SN2/E1/E2 Reaction: Wrap Up And Cautions, by @azmanam Congratulations! You now have all the information you …

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Guest Post on SN1/SN2/E1/E2 (4): The Electrophile

Guest Post on SN1/SN2/E1/E2 (4): The Electrophile

November 14, 2013

For the previous posts in Adam’s series on the SN1/SN2/E1/E2, see Part 1 Part 2 Part 3. – James Three And A Half Steps To Any Substitution or Elimination Reaction, Step 2: The Nature of The Electrophile by…

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Guest Post on SN1/SN2/E1/E2 (2): Three And A Half Steps To Any Substitution Or Elimination Reaction

Guest Post on SN1/SN2/E1/E2 (2): Three And A Half Steps To Any Substitution Or Elimination Reaction

November 7, 2013

The second in a series of guest posts on SN1/SN2/E1/E2 by Chemistry Blog author and “instructor of organic chemistry at a small Midwestern liberal arts college” @azmanam  . For the first post, click here.…

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Free Radical Reactions

Free Radical Reactions

July 30, 2013

With rare exceptions, until now every reaction we’ve discussed (acid-base, substitution, elimination, addition) has involved the formation of bonds between an electron pair donor (Lewis base) and an electron pai…

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The 2 Most Important Reactions of Alkynes

The 2 Most Important Reactions of Alkynes

May 1, 2013

With the series of posts on alkenes in the can, let’s move on and talk about a closely related functional group that shares many reactions in common with alkenes: acetylenes, or as they are more commonly referre…

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Wrapup: The Quick N’ Dirty Guide To SN1/SN2/E1/E2

Wrapup: The Quick N’ Dirty Guide To SN1/SN2/E1/E2

January 18, 2013

The previous several posts dealt with an approach to solving substitution and elimination problems that can only be described as a Quick N’ Dirty Guide to SN1/SN2/E1/E2. The basic premise is this: given 15-20 mi…

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Deciding SN1/SN2/E1/E2 (4) – The Temperature

Deciding SN1/SN2/E1/E2 (4) – The Temperature

December 19, 2012

The Quick N’ Dirty Guide To Determining SN1/SN2/E1/E2, Part 4 In previous installations of the Quick N’ Dirty Guide, we’ve examined the substrate, the base/nucleophile, and the solvent. Today, weR…

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