Experiment 18: Transesterification Catalyzed by an N-Heterocyclic Carbene

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Transesterification

Due Dates:

19 Apr / 20 Apr

A/B

Chemical Safety Information:

Reagents, Products, and Solvents (if available)
methanol mesitylamine (2,4,6-trimethylaniline) (6) chlorotrimethylsilane
ethyl acetate aq. glyoxal solution (7) paraformaldehyde
acetic acid N,N'-dimesitylethanediimine (8) potassium bicarbonate
acetone 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (9)

deuterated chloroform

dichloromethane benzyl alcohol (1a) 4-Fluorobenzyl alcohol (1b)
4-Chlorobenzyl alcohol (1c) 4-Bromobenzyl alcohol (1d) 3-Nitrobenzyl alcohol (1e)
Piperonyl alcohol (1f) 4-Nitrobenzyl alcohol (1g)

vinyl acetate (2)

benzyl acetate (4a) 4-Fluorobenzyl acetate (4b) 4-Chlorobenzyl acetate (4c)
4-Bromobenzyl acetate (4d) 3-Nitrobenzyl acetate(4e) Piperonyl acetate (4f)
4-Nitrobenzyl acetate (4g)    

 

Experimental Spectra:

 

Transesterification Starting Material and Precursors

Stock Mesitylamine 1H-NMR FID (FOR REFERENCE ONLY)

Sample Substituted Benzyl Alcohols (1a-g) 1H-NMR Spectra (FOR REFERENCE ONLY)

Sample NMR Spectra for Transesterification Diimine (not available for submission for credit)

Sample 1H-NMR Spectra for Imidazolium Salt (not available for submission for credit)

Stock 1H-NMR FID of Diimine 8 (available for submission for credit, see laboratory manual for details)

Stock IR of Diimine 8 (available for submission for credit, see laboratory manual for details)

Stock 1H-NMR FID of Imidazolium Salt 9 (available for submission for credit, see laboratory manual for details)

Stock IR of Imidazolium Salt 9 (available for submission for credit, see laboratory manual for details)

 

Transesterification Substituted Benzyl Acetates

Sample 1H-NMR Spectra for Transesterification Substituted Benzyl Acetates (4a-g) (not available for submission for credit)

Stock NMR FID of Benzyl Acetate (4a) (available for submission for credit, see laboratory manual for details)

Stock NMR FID of 4'-Fluorobenzyl Acetate (4b)  (available for submission for credit, see laboratory manual for details)

Stock NMR FID of 4'-Chlorobenzyl Acetate (4c) (available for submission for credit, see laboratory manual for details)

Stock NMR FID of 4'-Bromobenzyl Acetate (4d) (available for submission for credit, see laboratory manual for details)

Stock NMR FID of 3'-Nitrobenzyl Acetate (4e) (available for submission for credit, see laboratory manual for details)

Stock NMR FID of Piperonyl Acetate (4f) (available for submission for credit, see laboratory manual for details)

Stock NMR FID of 4'-Nitrobenzyl Acetate (4g) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of Benzyl Acetate (4a) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of 4-Fluorobenzyl Acetate (4b) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of 4-Chlorobenzyl Acetate (4c) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of 4-Bromobenzyl Acetate (4d) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of 3-Nitrobenzyl Acetate (4e) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of Piperonyl Acetate (4f) (available for submission for credit, see laboratory manual for details)

Stock GC-MS of 4-Nitrobenzyl Acetate (4g) (available for submission for credit, see laboratory manual for details)

Stock IR of Benzyl Acetate (4a) (available for submission for credit, see laboratory manual for details)

Stock IR of 4-Fluorobenzyl Acetate (4b) (available for submission for credit, see laboratory manual for details)

Stock IR of 4-Chlorobenzyl Acetate (4c) (available for submission for credit, see laboratory manual for details)

Stock IR of 4-Bromobenzyl Acetate (4d) (available for submission for credit, see laboratory manual for details)

Stock IR of 3-Nitrobenzyl Acetate (4e) (available for submission for credit, see laboratory manual for details)

Stock IR of Piperonyl Acetate (4f) (available for submission for credit, see laboratory manual for details)

Stock IR of 4-Nitrobenzyl Acetate (4g) (available for submission for credit, see laboratory manual for details)