Prev. Article Next Article Table of Contents

Article

Grignard Synthesis of Various Tertiary Alcohols

Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

T. Stephen Everett

Goucher College, Department of Chemistry, 1021 Dulaney Valley Road, Baltimore, MD 21204-2794

J. Chem. Educ., 1998, 75 (1), p 86

DOI: 10.1021/ed075p86

Publication Date (Web): January 1, 1998

Section:

History, Education, and Documentation

Abstract

A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data. Once a product is identified retro-synthetic considerations point to which alkyl halide and ketone were required as starting materials. This laboratory exercise in organic synthesis incorporates anhydrous techniques, distillation, and infrared analysis.

RX + Mg ---> [RMgX] + R'R"C=O ---> [RR'R"COMgX] ---> RR'R"COH

Criteria

RX = C₂-C₅ 1' alkyl bromide (unbranched)

R'R"C=O = C₃-C₅ ketone

RR'R"COH = C₆-C₉ 3' alcohol

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

IR Spectroscopy

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment
Roy D. Pointer , Michael A. G. Berg
Journal of Chemical Education2007 84 (3), 483
- Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment
  Roy D. Pointer , Michael A. G. Berg
  Journal of Chemical Education2007 84 (3), 483
  A commercially available Grignard reagent (3.0 M solution of phenyl magnesium bromide in ether) was used in a convenient Grignard synthesis in a second-year organic chemistry laboratory without any of the typical failures associated with the Grignard ...
  Abstract | Hi-Res PDF | PDF w/ Links
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course
James A. Ciaccio , Roxana P. Bravo , Antoinette L. Drahus , John B. Biggins , Rosalyn V. Concepcion and David Cabrera
Journal of Chemical Education2001 78 (4), 531
- Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course
  James A. Ciaccio , Roxana P. Bravo , Antoinette L. Drahus , John B. Biggins , Rosalyn V. Concepcion and David Cabrera
  Journal of Chemical Education2001 78 (4), 531
  We have developed an undergraduate organic laboratory experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive α-chiral ketone. Students isolate a single diastereomer of (+/-)-1,2-diphenyl-1,2-...
  Abstract | Hi-Res PDF | PDF w/ Links
Introduction to Homogeneous Catalysis: Carbon-Carbon Bond Formation Catalyzed by a Defined Palladium Complex
Wolfgang A. Herrmann , Volker P. W. Böhm and Claus-Peter Reisinger
Journal of Chemical Education2000 77 (1), 92
- Introduction to Homogeneous Catalysis: Carbon-Carbon Bond Formation Catalyzed by a Defined Palladium Complex
  Wolfgang A. Herrmann , Volker P. W. Böhm and Claus-Peter Reisinger
  Journal of Chemical Education2000 77 (1), 92
  In this laboratory experiment students synthesize a phosphine ligand, P(o-tol)3, and with it the corresponding cyclometallated Pd(II) complex. This complex is an extremely active (pre)catalyst for C-C-bond-forming reactions (e.g. the Heck vinylation or ...
  Abstract | Hi-Res PDF | PDF w/ Links