Ochem II Reagents

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59 Terms

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halogenation on benzene

X2/FeX3

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sulfonation on benzene

SO3/H2SO4

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how do you reverse sulfonation/nitration?

H3O+/H2O

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nitration

HNO3/HCl

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FC alkylation

R-X/AlX3

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FC acylation

RCOX/AlX3

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reduce aldehydes/ketones to alkanes

wolffe kishner/clemmenson reduction

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NO2 —> NH2

H2/ Pd/C

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NH2 —> NO2

F3COOOH

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NH2 —> N2+

HONO (HCl, NaONO)

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N2+ —> Cl, Br, CN

CuCl, CuBr, CuCN

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N2+ —> I

KI

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N2+ —> F

HBF4

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N2+ —> OH

H2O/acid

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N2+ —> H/D

H3PO2/D3PO2

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oxidation of aromatic alkanes (need one H available)

KMnO4

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oxidation of alcohols

CrO3/H2O (ketones/carboxylic acids)

CrO3/dry pyridine (for ketones/aldehydes)

PCC (aldehydes)

Swern oxidation: 1. DMSO, (COCl)2 2. Et3N (aldehydes)

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oxidative cleavage of vicinol diols

HIO4

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imine

R2CO + R-NH2, acid

<p>R<sub>2</sub>CO + R-NH<sub>2</sub>, acid </p>
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enamine

R2CO + R2-NH, acid

<p>R<sub>2</sub>CO + R<sub>2</sub>-NH, acid </p>
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adding R groups to ketones

  1. R-Li, R-MgX

  2. H2O

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reduction of C=O

  1. LiAlH4/NaBH4 (*NaBH4 cannot be used to reduce carboxylic acids)

  2. H2O

or meerwein-ponndorf-verley-oppenaner equilibration (for aldehydes and ketones)

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making C=C bonds

Wittig reaction:

R2C=O + ylide (Ph3P=CR2) —> R2C=CR2

<p>Wittig reaction:</p><p>R<sub>2</sub>C=O + ylide (Ph<sub>3</sub>P=CR<sub>2</sub>) —&gt; R<sub>2</sub>C=CR<sub>2</sub></p>
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making carboxylic acids from CO2

  1. R-Li/R-Mg-X + CO2

  2. acid

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b-keto carboxylic acid —> ketone

decarboxylation (heat)

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alkene —> carboxylic acid

ozonelysis

  1. O3

  2. H2O2

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making ester

  • fischer esterification: carboxylic acid + ROH/acid

  • SN2: 1. carboxylic acid + base 2. R-I

  • carboxylic acid + H2CN2 (diazomethane)

  • bayer-villager

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carboxylic acid —> acyl chloride

SOCl2

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carboxylic acid —> amide

  1. DCC

  2. R-NH2 or R2NH

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2 carboxylic acid —> anhydride

300 C

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adding R groups to carboxylic acids

  1. R-Li (2 eq. for one addition)

  2. H3O+

you make geminal diols, so you can use acid/base to reverse it into ketone with new R group

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alcohols —> alkyl bromide/chloride

PBr3/SOCl2

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alkyl halide —> carbon nucleophiles

2 Li+ or Mg

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ester —> aldehyde

DIBAL-H / -78 C

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acyl chloride —> amide

HNR2

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anhydride —> amide

R2NH

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R-I —> R-CN (nitrile)

KCN (SN2)

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acyl chloride/ester/amide/nitrile —> carboxylic acid

NaOH or H3O+/H2O

(*if you use base, you have to adjust pH in the end with acid or else you have carboxylate ion)

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RR’CO —> RCOOR’

bayer-villager: ketone + peroxy acid —> ester

rearrangement!

<p>bayer-villager: ketone + peroxy acid —&gt; ester</p><p>rearrangement!</p>
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RCOR’ —> R‘CONHR

beckmann rearrangement

ketone + NH2OH/H3O+ —> oxime + acid/H2O —> amide

<p>beckmann rearrangement</p><p>ketone + NH<sub>2</sub>OH/H<sub>3</sub>O+ —&gt; oxime + acid/H<sub>2</sub>O —&gt; amide</p>
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add one more carbon to acyl chloride

wolffe rearrangement

acyl chloride + CH2N2 (diazomethane) —> ketene + H2O —> one more carbon added

<p>wolffe rearrangement</p><p>acyl chloride + CH<sub>2</sub>N<sub>2</sub> (diazomethane) —&gt; ketene + H<sub>2</sub>O —&gt; one more carbon added</p>
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add one more carbon to carboxylic acid

arndt-einstert rearrangement (basically wolffe but we convert carboxylic acid to acyl chloride first)

  1. SOCl2 2. CH2N2 3. H3O+/H2O

<p>arndt-einstert rearrangement (basically wolffe but we convert carboxylic acid to acyl chloride first)</p><ol><li><p>SOCl<sub>2</sub> 2. CH<sub>2</sub>N<sub>2</sub> 3. H<sub>3</sub>O+/H<sub>2</sub>O</p></li></ol><p></p>
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acyl chloride —> isocyanate

curtius rearrangement

  1. NaN3

  2. heat or hv

<p>curtius rearrangement</p><ol><li><p>NaN<sub>3</sub></p></li><li><p>heat or hv</p></li></ol><p></p>
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isocyanate —> products

carbamate (use ROH)

amine (use H2O)

urea derivative (RNH2)

<p>carbamate (use ROH)</p><p>amine (use H<sub>2</sub>O)</p><p>urea derivative (RNH<sub>2</sub>)</p>
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primary amide —> amine

hoffman rearrangement

  1. Br2

  2. H2O/KOH

<p>hoffman rearrangement</p><ol><li><p>Br<sub>2</sub></p></li><li><p>H<sub>2</sub>O/KOH</p></li></ol><p></p>
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halogenation at a-position

X2/acid or X2/base (overreacts!)

no F!

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keto-enol tautomerization

acid/base

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methyl ketone —> carboxylate ion

haloform/iodoform reaction

I2/NaOH, H2O

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making a-B unsaturated ketone

aldol condensation (acid/base)

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alkylation at a-position

  1. LDA (irreversible!)

  2. R-I (SN2)

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enamine —> iminimum —> alkylated ketone/aldehyde (with one more carbon added)

dean-stork alkylation

enamine + R-I —> iminium + acid —> alkylated ketone/aldehyde with one more carbon added

<p>dean-stork alkylation</p><p>enamine + R-I —&gt; iminium + acid —&gt; alkylated ketone/aldehyde with one more carbon added</p>
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1,5 dicarbonyl

michael addition

ketone + a-B unsaturated ketone (prefers 1,4 addition) in NaOH/H2O

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a-B unsaturated ketone selectivity

+ R-Li/R-MgX prefers 1,2 addition

+ R2CuLi prefers 1,4 addition

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ester —> b-keto ester

claisen condensation *very useful for synthesis!

  1. NaOR/HOR

  2. adjust pH levels (bc a-H very acidic!) — pH = 7 makes ester, pH = 1 makes b-keto acid

<p>claisen condensation *very useful for synthesis!</p><ol><li><p>NaOR/HOR</p></li><li><p>adjust pH levels (bc a-H very acidic!) — pH = 7 makes ester, pH = 1 makes b-keto acid</p></li></ol><p></p>
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cannizaro reaction

base catalyzed (NaOH): 2 benzaldehyde —> benzoic acid ion + benzoic alcohol

<p>base catalyzed (NaOH): 2 benzaldehyde —&gt; benzoic acid ion + benzoic alcohol</p>
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meerwein-ponndorf-verley-oppenaner equilibration

R2CO + 1. Al(OCH(CH3)2)3 2. H2O —> R2OH

<p>R<sub>2</sub>CO + 1. Al(OCH(CH<sub>3</sub>)<sub>2</sub>)<sub>3<sup> </sup></sub>2. H<sub>2</sub>O —&gt; R<sub>2</sub>OH</p>
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mannich reaction

knowt flashcard image
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swern oxidation

1. DMSO, (COCl)2 2. Et3N (aldehydes)

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zipper reaction

  1. NaNH2

  2. H2O

making terminal alkynes with 100% yield

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