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Appendix: The Greener Organic Chemistry Reaction Index. Operative Reaction Mechanisms, Experimental Techniques, and Greener Principles for Each Undergraduate Reaction

Appendix: The Greener Organic Chemistry Reaction Index. Operative Reaction Mechanisms, Experimental Techniques, and Greener Principles for Each Undergraduate Reaction

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258



Appendix



As a final note, it is important to appreciate that the reactions in this appendix all

have green elements to them—they are not perfectly green processes. Indeed, some

have features that would benefit from “greening.” This is always a critical point to

discuss with students, and will hopefully provide an impetus for even greener experiments to be developed in years to come.



Electrophilic addition



Electrophilic addition



Electrophilic addition



Electrophilic addition

Electrophilic addition



Electrophilic addition

Electrophilic addition

Electrophilic addition



Electrophilic addition

Electrophilic addition/

nucleophilic addition

Electrophilic addition/

pericyclic



Electrophilic aromatic

substitution

Electrophilic aromatic

substitution



1.



2.



3.



4.

5.



6.

7.

8.



9.

10.



12.



13.



11.



Reaction Mechanism



Entry



Alkylation



Acylation of ferrocene



Hetero Diels-Alder reaction



Halohydrin formation

Iodolactonization



Alkene epoxidation

Alkene iodochlorination

Alkene oxidation/cleavage



Alkene chlorination

Alkene epoxidation



Alkene bromination



Alkene bromination



Alkene bromination



Transformation



JCE 2007, 84, 692–693



JCE 2008, 85, 261–262



JCE 2006, 83, 270–272



JCE 1985, 62, 638

JCE 2006, 83, 921–922



JCE 2004, 81, 1018–1019

JCE 2008, 85, 962–964

JCE 2000, 77, 1627–1629



JCE 2003, 80, 1319–1321

JCE 2004, 81, 1187–1190



GCLR 2010, 3, 39–47



JCE 2005, 82, 306–310



JCE 2005, 82, 306–310



Journal



MI, MS, LE, LD, GF,

RE, CC

H, VF, RE



MI, VF, LE, GF, LD, D/

RE



H, VF, R

MS, LE, LD, GF, RE



MS, LE, LD, GF, RE

H, LE, LD, GF, RE, VF

MS, H, VF, R



MS, LD, GF, RE

MS, LE, LD, GF



MS, VF, H, LE, LD, RE



MS, H, VF, R



MS, H, VF



Techniques



(continued)



Catalytic, greener reagent,

solvent-free, atom efficiency,

microwave heating

Catalytic, greener reagent,

microwave heating

Greener, recyclable reagent



Safer reagent, alternative

reaction solvent, product

recycling

Greener reagents, alternative

reaction solvent, atom

efficiency, product recycling

Catalytic, greener reagent,

aqueous solvent, atom efficiency

Greener reagent

Catalytic, greener reagent,

alternative reaction solvent,

atom efficiency

Aqueous solvent

Alternative reaction solvent

Catalytic, greener reagent,

aqueous solvent

Aqueous solvent

Aqueous solvent



Greener Principles



Appendix

259



Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic aromatic

substitution

Electrophilic substitution

Electrophilic substitution/

nucleophilic acyl substitution

Electrophilic substitution/

rearrangement/nucleophilic

addition/decarboxylation

Elimination

Fermentation



Ionic liquid formation



14.



27.



25.

26.



24.



22.

23.



21.



20.



19.



18.



17.



16.



15.



Reaction Mechanism



Entry



Journal



Deep eutectic solvent

synthesis



Alcohol dehydration

Alcohol production



EC 2005, 42 (1), 12–15



JCE 1993, 70, 493–495

JCE 2010, 87, 708–710



JCE 1999, 76, 1717



JCE 2008, 85, 834–835

JCE 2010, 87, 190–193



α-Fluorination

Haloform reaction



Hofmann rearrangement



GC 2001, 3, 267–270



GC 2001, 3, 267–270



JCE 2005, 82, 616–617



Porphyrin formation



Porphyrin formation



Nitration



JCE 2008, 85, 1426–1428



JCE 1997, 74, 324



Fries rearrangement



Iodination



TCE 2001, 6, 25–27



JCE 2006, 83, 1665–1666



TCE 1998, 3, 1–6



Friedel-Crafts acylation



Dipyrromethane formation



Bromination



Transformation



Techniques



ES, H



H, LE, LD, GF

H, D



MS, H, VF, R



MS, H, VF, RE

MS, H, VF



H, CC



MI, LE, GF, RE, CC



MS, H, VF, R



ES, VF, R



MI, LE, LD, GF, RE



MS, LE, GF, SE



MS, GF, LD, VF, LE,

RE, D

H, VF



Catalytic, greener reagent

Biocatalytic, greener reagent,

renewable feedstock

Greener product



Greener reagent



Greener reagent

Aqueous solvent



Solvent-free



Aqueous solvent, renewable

feedstock

Solvent-free, microwave heating



Recyclable reagent, microwave

heating

Greener reagent



Catalytic, greener reagent,

aqueous solvent, atom efficiency

Solvent-free



Greener reagent



Greener Principles



260

Appendix



Metathesis

Metathesis



Metathesis

Metathesis

Metathesis



Metathesis



Nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution

Nucleophilic acyl substitution



Nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution



28.

29.



30.

31.

32.



33.



34.

35.

36.

37.

38.

39.



40.



41.



42.

43.



44.

45.

46.



Esterification

Esterification

Phthalimide synthesis



Diimide formation

Ester hydrolysis



Coffee ground degradation



Ring-opening metathesis

polymerization

Amide formation

Amide formation

Amide hydrolysis

Amine formylation

Aspirin synthesis

Aspirin, acetanilide,

phenacetin, acetaminophen

synthesis

Claisen condensation



Ring-closing metathesis

Ring-closing metathesis

Ring-opening metathesis

polymerization



Cross-metathesis

Ring-closing metathesis



JCE 1993, 70, 493–495

JCE 2009, 86, 227–229

JCE 1992, 69, 938–939



JCE 2008, 85, 1649–1651

JCE 2006, 83, 634–636



JCE 2001, 78, 1669–1671



JCE 2003, 80, 1446–1447



JCE 2003, 80, 1444–1445

JCE 2002, 79, 1344

JCE 2009, 86, 227–229

JCE 2009, 86, 227–229

JCE 2006, 83, 628–631

JCE 2000, 77, 356–357



JCE 1999, 76, 661–665



JCE 2010, 87, 721–723

JCE 2007, 84, 1998–2000

JCE 1993, 70, 165–167



JCE 2006, 83, 283–284

JCE 2007, 84, 1995–1997



SG, H, R

MI, MS, LE, LD, GF,

RE, R

H, LE, LD, GF, D

MI, MS, RE, LE, LD, GF

SG, MI, VF, R



H, LE, GF, LD, RE, T,

R

H, SX, RE



VF

MI, VF, R

MI, MS, VF

MI, MS, VF

MI, ES, VF, R

MI, VF, R



MS, IA, VF, RE, VF



MS, RE, CC, VF, R

MS, H, VF, ST, IA, CC,

RE

MS, IA, GF, RE

MS, H, RE, VF, IA

H, VF



(continued)



Consumer product recycling,

renewable feedstock

Solvent-free

Aqueous solvent, microwave

heating

Catalytic, greener reagent

Catalytic, microwave heating

Microwave heating



Solvent-free



Greener reagent

Microwave heating

Microwave heating

Microwave heating

Catalytic, microwave heating

Catalytic, aqueous solvent,

microwave heating



Catalytic, greener reagent

Catalytic, greener reagent

Catalytic, greener reagent,

aqueous solvent, renewable

feedstock, product recycling

Catalytic, greener reagent



Catalytic, greener reagent

Catalytic, greener reagent



Appendix

261



Reaction Mechanism



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Nucleophilic acyl substitution



Entry



47.



48.



49.



50.



51.



52.



53.



54.



55.



56.



57.



Transesterification (biodiesel

synthesis)



Transesterification (biodiesel

synthesis)



Transesterification (biodiesel

synthesis)



Transesterification (biodiesel

synthesis)



Transesterification (biodiesel

synthesis)



Transesterification (biodiesel

synthesis)



Polyethylene terephthalate

degradation

Polyethylene terephthalate

degradation

Polyethylene terephthalate

degradation

Transesterification



Polylactic acid degradation



Transformation



Journal



JCE 2011, 88, 197–200



TCE 2009, 14, 98–104



JCE 2006, 83, 260–262



JCE 2006, 83, 257–259



JCE 2007, 84, 296–298



TCE 2005, 10, 130–132



JCE 2010, 87, 423–425



JCE 2010, 87, 519–521



JCE 1999, 76, 1525–1526



JCE 2003, 80, 79–82



JME 2008, 30, 257–280



Techniques



MS, H



ES, MI



MS, H, LE



MS, H, LE, LD



MS, H, C



MS, H, LE, VF



MS, VF, RE, D



MS, H, VF



MS, H, LE, VF



MS, H, VF, GF



MS, H, RE



Biocatalytic, greener reagent,

low-solvent usage

Consumer product recycling,

renewable feedstock, greener

product

Consumer product recycling,

renewable feedstock, greener

product

Consumer product recycling,

renewable feedstock, greener

product

Consumer product recycling,

renewable feedstock, greener

product

Consumer product recycling,

renewable feedstock, microwave

heating, greener product

Consumer product

recycling,renewable feedstock,

greener product



Consumer product recycling



Consumer product recycling



Consumer product recycling,

renewable feedstock

Consumer product recycling



Greener Principles



262

Appendix



Barbier (Grignard type)

reaction

Cannizzaro reaction

Cannizzaro reaction



Cellulose degradation



Nucleophilic addition



Nucleophilic addition



Nucleophilic addition

Nucleophilic addition



Nucleophilic addition



Nucleophilic addition



66.



67.



68.

69.



70.



71.



Cellulose degradation



Aldol condensation



Aldol condensation



Nucleophilic addition



65.



Aldehyde reduction

Aldehyde reduction

Aldehyde reduction



Nucleophilic addition

Nucleophilic addition

Nucleophilic addition



62.

63.

64.



61.



Acetal formation



Cu(II) phthalocyanine

complex formation

Pechmann condensation



Nucleophilic acyl substitution/

dehydration

Nucleophilic acyl substitution/

electrophilic aromatic

substitution/dehydration

Nucleophilic addition



59.



60.



Transesterification (biodiesel

synthesis)



Nucleophilic acyl substitution



58.



TCE 2000, 5, 315–316



JCE 2008, 85, 546–548



JCE 2009, 86, 85–86

JCE 2004, 81, 1794–1795



JCE 1998, 75, 85



JCE 2006, 83, 1871–1872



JCE 2007, 84, 475–476



JCE 2006, 83, 285–286

JCE 2005, 82, 1674–1675

JCE 2011, 88, 322–324



JCE 2001, 78, 70–72



JCE 2011, 88, 319–321



JCE 2011, 88, 86–87



JCE 2011, 88, 201–203



H, VF



SG, VF

SG, H, LE, VF, GF, LD,

RE

H, VF, D



MS, GF, LE, LD, RE



MS, LE, LD, GF, RE



MS, VF



MS, VF

MS, LE, LD, RE

MS, H, LE, LD, RE



MS, H, VF, R



ES, H, VF, R



SG, MI



MS, H, LD, GF



Consumer product recycling,

renewable feedstock

Consumer product recycling,

renewable feedstock

(continued)



Solvent-free

Solvent-free



Consumer product recycling,

renewable feedstock, greener

product

Solvent-free, catalytic, greener

reagent, microwave heating

Solvent-free, catalytic,greener

reagent, recyclable reagent,

atom efficiency

Catalytic, greener reagent,

aqueous solvent

Aqueous solvent

Greener reagent

Catalytic, greener reagent, atom

efficiency

Catalytic, greener reagent,

aqueous solvent, atom efficiency

Catalytic, greener reagent,

renewable feedstock, atom

efficiency

Aqueous solvent



Appendix

263



Ketone reduction

Ketone reduction

Ketone reduction

Mannich reaction



Michael reaction



Nucleophilic addition



Nucleophilic addition



Nucleophilic addition



Nucleophilic addition

Nucleophilic addition



Nucleophilic addition



Nucleophilic addition



Nucleophilic addition



Nucleophilic addition

Nucleophilic addition

Nucleophilic addition

Nucleophilic addition



Nucleophilic addition



Nucleophilic addition



73.



74.



75.



76.

77.



78.



79.



80.



81.

82.

83.

84.



85.



86.



Michael reaction/alkene

reduction



Ketone reduction



Ketone reduction



Ketone reduction



Ketone reduction

Ketone reduction



Horner–Wadsworth–

Emmons reaction

Ketone reduction



Grignard reaction



Creatine synthesis



Nucleophilic addition



72.



Transformation



Reaction Mechanism



Entry



JCE 2011, 88, 322–324



JCE 2010, 87, 194–195



TCE 2008, 13, 344–347

GCLR 2008, 1, 149–154

JCE 1996, 73, A104-A105

JCE 2006, 83, 943–946



JCE 2002, 79, 727–728



JCE 2006, 83, 1049–1051



JCE 2005, 82, 1049–1050



JCE 1986, 63, 909

JCE 1998, 75, 630–631



JCE 2005, 82, 1055–1056



TCE 2005, 10, 300–302



JCE 2009, 86, 227–229



JCE 2006, 83, 1654–1657



Journal



LE, LD, RE



CC, RE, H, VF, R



MS, H

MS, H, D, GF, LD, RE

MI, VF, R

MS, H, VF, R, LE, RE



MS, H, VF, LE, LD, RE,

CC

MS, GF, LE, LD, RE,

CC

H, VF, LE, LD, GF, RE



SG, MI, LE, LD, GF,

RE

MS, LE, LD, GF, RE/D

MS, GF, LD, RE, D



MI, MS, LE, LD, GF,

RE, R

MS, H, VF, R



MS, VF, R



Techniques



Biocatalytic, greener reagent,

aqueous solvent

Greener reagent

Catalytic, greener reagent

Microwave heating

Alternative and recyclable

reaction solvent, atom

efficiency

Catalytic, greener reagent, atom

efficiency

Catalytic, greener reagent



Biocatalytic, greener reagent



Biocatalytic, greener reagent



Aqueous solvent

Biocatalytic, greener reagent



Solvent-free, microwave heating



Aqueous solvent



Catalytic, greener reagent,

aqueous solvent, atom efficiency

Microwave heating



Greener Principles



264

Appendix



102.



101.



100.



99.



Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration



Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration



98.



97.



96.



95.



Coumarin formation



Coumarin formation



Biginelli reaction



Aldol condensation



Aldol condensation



Aldol condensation



Aldol condensation



Aldol condensation



Wittig reaction

Wittig reaction

Wittig reaction

Wittig reaction

Wittig reaction

Knoevenagel condensation/

Michael addition/annulation

Passerini reaction



Nucleophilic addition

Nucleophilic addition

Nucleophilic addition

Nucleophilic addition

Nucleophilic addition

Nucleophilic addition(s)/

dehydration(s)/decarboxylation

Nucleophilic addition(s)/

nucleophilic acyl substitution

Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration



88.

89.

90.

91.

92.

93.



94.



Oxazolidinone formation



Nucleophilic addition



87.



PAC 2001, 73, 1257–1260;

GC 2000, 2, 245–247

PAC 2001, 73, 1257–1260;

GC 2000, 2, 245–247



JCE 2009, 86, 730–732



TCE 2011, 16, 23–25



JCE 2004, 81, 1345–1347



JCE 2007, 84, 475–476



JCE 1994, 71, A142, A144



JCE 2009, 86, 488–493



JCE 2009, 86, 1077–1079



JCE 2004, 81, 1492–1493

JCE 2007, 84, 119–121

JCE 2007, 84, 2004–2006

JCE 2007, 84, 119–121

JCE 1978, 55, 813

JCE 2007, 84, 1477–1479



JCE 2005, 82, 1229–1230



MS, VF



SG, VF



MS, H, SG, VF



ES, VF, R



SG, VF, R



MS, H, VF



MI, VF



SG, T, VF, R



SG, VF, R

MS, GF, RE

SG, MI, LE, RE, CC

H, MS, GF, RE, R

H, MS, GF, VF, R

MI, MS, LE, LD, GF,

RE

MS, VF, R



MS, LE, LD, GF, RE



Catalytic, greener reagent,

solvent-free, improved energy

efficiency, atom efficiency

Catalytic, greener reagent,

solvent-free

Catalytic, greener reagent,

aqueous solvent

(continued)



Aqueous solvent, renewable

feedstock

Solvent-free

Solvent-free

Solvent-free, microwave heating

Solvent-free

Aqueous solvent

Aqueous/greener solvent,

microwave heating

Aqueous solvent, atom

efficiency

Catalytic, greener reagent,

solvent-free, atom efficiency

Microwave heating, atom

efficiency

Catalytic, greener reagent,

aqueous solvent, atom

efficiency

Catalytic, greener reagent,

solvent-free, atom efficiency

Solvent-free, atom efficiency



Appendix

265



Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration



Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration



103.



105.



113.



112.



Heterocyclic syntheses (e.g.,

benzimidazole,

phthalimide)

Heterocyclic syntheses (e.g.,

pyrrole, oxazoline,

thiazoline, indole)

Aldol condensation/Michael

reaction



Semicarbazone formation



Nucleophilic addition/

dehydration

Nucleophilic addition/

dehydration or nucleophilic

acyl substitution/dehydration

Nucleophilic addition/

dehydration or nucleophilic

acyl substitution/dehydration

Nucleophilic addition/

dehydration/nucleophilic

addition



110.



111.



Knoevenagel condensation



Nucleophilic addition/

dehydration



Knoevenagel condensation



Imine formation



Imine formation



Imidazole synthesis



Hantzsch reaction



Dioxolanone synthesis



Transformation



109.



108.



107.



106.



104.



Reaction Mechanism



Entry



JCE 2005, 82, 468–469



JCE 2006, 83, 634–636



JCE 2006, 83, 632–633



JCE 2004, 81, 108



JCE 2009, 86, 227–229



TCE 2007, 12, 324–326



JCE 2006, 83, 1221–1224



JCE 2006, 83, 929–930



JCE 2006, 83, 1658–1660



JCE 2010, 87, 628–630



TCE 2003, 8, 33–36



Journal



SG, MS, H, VF



MI, MS, LE, LD, GF,

RE, R, CC



SG, MI, VF, R



SG, VF, R



MI, MS, VF



MS, VF



VF, MS, H, VD



SG, R



MI, VF, R



MS, H, SG, VF, R



MI, CC, RE



Techniques



Solvent-free, renewable

feedstock, atom efficiency



Solvent-free, microwave heating



Solvent-free, atom efficiency,

microwave heating



Alternative reaction solvent,

atom efficiency, microwave

heating

Solvent-free



Alternative reaction solvent,

atom efficiency

Catalytic, greener reagent,

aqueous solvent, atom efficiency



Solvent-free, atom efficiency



Low-solvent usage, improved

energy efficiency, atom

efficiency

Microwave heating



Microwave heating



Greener Principles



266

Appendix



127.



126.



125.



124.



123.



122.



121.



120.



119.



118.



117.



116.



115.



114.



Nucleophilic addition/

dehydration/nucleophilic

addition/hydrolysis

Nucleophilic addition/

electrophilic addition

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

JCE 1980, 57, 438

JCE 1987, 64, 371–372



Alcohol oxidation



JCE 1991, 68, 1048–1049



QN 2009, 32, 1667–1669



JCE 1985, 62, 519–521



JCE 1982, 59, 981



JCE 1982, 59, 862



JCE 1981, 58, 824



Alcohol oxidation



Alcohol oxidation



Alcohol oxidation



Alcohol oxidation



Alcohol oxidation



Alcohol oxidation



Alcohol oxidation



TCE 2010, 15, 115–116



JCE 2001, 78, 66–67



Alcohol oxidation



Alcohol oxidation



TCE 2004, 9, 30–31



Alcohol oxidation



JCE 2003, 80, 907–908



JCE 2011, 88, 322–324



Alkene epoxidation



Alcohol oxidation



JCE 2004, 81, 874–876



Coumarin formation



MS, VF, H, GF, RE, R



MS, VF, H, GF, RE, R



MS, LE, LD, RE, R



MS, H, LE, LD, RE



D, LE, LD



MS, H, D, LE, LD



D



MS, H, D, LE, LD



MS, LE, LD, GF, R



MS, H, LE, LD, RE



SG, H, LE, VF, LD, GF,

RE

SG, H, LE, LD, GF, RE



MS, LE, LD, GF, RE



MS, H, VF, R



Greener reagent, recyclable

reagent

Greener reagent, recyclable

reagent

(continued)



Catalytic, greener reagent



Greener reagent



Greener reagent



Greener reagent



Greener reagent



Greener reagent



Catalytic, greener reagent,

aqueous solvent

Product recycling



Solvent-free



Catalytic, greener reagent,

aqueous solvent, atom

efficiency

Catalytic, greener reagent, atom

efficiency

Solvent-free



Appendix

267



Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination



Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

elimination



Nucleophilic addition/

elimination

Nucleophilic addition/

elimination

Nucleophilic addition/

nucleophilic acyl substitution

Nucleophilic addition/

rearrangement

Nucleophilic addition/

rearrangement



128.



133.



136.



140.



139.



138.



137.



135.



134.



132.



131.



130.



129.



Reaction Mechanism



Entry



JCE 2005, 82, 1837–1838

JCE 2008, 85, 1274–1275



Epoxide rearrangement



JCE 2010, 87, 640–642



JCE 1997, 74, 1225



JCE 2010, 87, 190–193



TCE 2004, 9, 370–373



JCE 2004, 81, 388–390



JCE 2007, 84, 852–854



Baeyer-Villiger reaction



Hydantoin synthesis



Wolff-Kischner reaction



Ketone oxidation



Ketone oxidation



Benzylic oxidation



Aldehyde oxidation



JCE 2011, 88, 652–656



JCE 2009, 86, 227–229



Alcohol oxidation



Alcohol oxidation



JCE 2010, 87, 981–984



JCE 2001, 78, 951–952



Alcohol oxidation



Alcohol oxidation



JCE 2006, 83, 268–269



Journal



Alcohol oxidation



Transformation



MS



LE, LD, GF, RE, VF, R



MI, VF, LE, LD, GF,

RE, R

MI, GF, RE



MS, H, VF



MS, H, VF, R



MS, VF, CC



MS, H, VF, R



MS, H, LE, LD, RE,

CC, IA, VF

MI, MS, GF, LE, LD,

RE

MS, LE, LD, GF, RE,

SB



MS, VF, RE, CC



MS, H, VF, RE, R



Techniques



Catalytic, greener reagent, atom

efficiency



Solvent-free



Greener reagent, aqueous

solvent

Microwave heating, alternative

reaction solvent

Microwave heating



Greener reagent



Catalytic, greener reagent



Greener reagent, recyclable

reagent

Catalytic, greener reagent,

microwave heating

Catalytic, greener reagents,

alternative reaction solvent,

renewable feedstock

Aqueous solvent



Greener reagent, recyclable

reagent

Greener reagent



Greener Principles



268

Appendix



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Appendix: The Greener Organic Chemistry Reaction Index. Operative Reaction Mechanisms, Experimental Techniques, and Greener Principles for Each Undergraduate Reaction

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