TY  - BOOK
AU  - Kelli S. Khuong, Fabio Agnelli, and Matthew A. Parker
TI  -  An Updated Simple SN2 Reaction for the Undergraduate Organic Laboratory: (Journal Article) 
T2  - American Chemical Society, Volume 100, Issue 1
SN  - 0021-9584
U1  - 540.7 
PY  - 0000///,January 102023///
CY  - Washington, United States
PB  - :American Chemical Society
KW  - Second-Year Undergraduate
KW  -  Organic Chemistry
KW  - Laboratory Instruction
KW  - Alkylation Ethers Reactions
KW  - Synthesis Thin Layer
KW  -  Chromatography
N1  - ***______{For Hard Copy, Please visit Library.}________***
N2  - Abstract:-

SN2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often less than ideal for reasons of toxicity/volatility and difficulty in TLC visualization. We report an updated methodology utilizing an alkyl tosylate, rather than a halide, as the electrophile. The SN2 reaction of 2-naphthol/sodium hydroxide with butyl p-toluenesulfonate is performed in a single 3 or 4 h lab period and affords a solid product in good yield. The tosylate electrophile gives students experience with a commonly encountered leaving group, is easily visualized on TLC, and has an improved safety profile.


UR  - https://pubs.acs.org/doi/epdf/10.1021/acs.jchemed.2c00794
ER  -