Organic Chemistry Reactions and Synthesis Overview
Explore a comprehensive overview of organic chemistry reactions, including esterification, oxidation, hydroboration, and reductions like Wolff-Kishner and Clemmensen. Dive into compound classifications such as carboxylic acids, ketones, and acid chlorides. Learn about key reagents and reactions essential for organic synthesis.
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The last, final, all-you-can eat, tail-end Drill and Practice
H What s my compound class ? N+ CrO3Cl- = pcc =pyridinium chlorochromate 1o OH O aldehyde K2Cr2O7 H2SO4 OH What s my compound class ? 1o OH O Carboxylic acid
Products class ? An ester O O H+ H O + + O H2 O reflux OH Reaction s name ? Fischer esterification Note !! pyridine O O H O + + H Cl O Cl What s my compound class? An Acid chloride
O3/in freon Zn/H+ H O 2 H H HgSO4/ H2SO4 + H2 O O Hint: keto-enol and Markovnikoff H2O2 /OH- BH3/neat or in THF H.C. Brown s 2 step hydroboration/oxidation O Name of reaction ? H
OH O H+/H2O Mg + dry ether C C Br O H+/H2O Mg dry ether C + 2 Br O OH C + OH OH O Li H+/H2O + dry ether C C
pcc 2o O OH K2Cr2O7 2o H2SO4 OH O My compound class ? ketones NR K2Cr2O7 not strong enough to oxidize 3o ROH K2Cr2O7 3o H2SO4 OH
+ Li - H O O neat Lio + + H2 KHSO4 heat O O + + Cl S OH HCl S O O O Then: O O - + S S + + O O Na O O Na Alkyl sulfonate synthesis Reaction s name ?_______________________________
KMnO4 O heat OH OH Mg/dry ether CO2(g) H+/H2O OH C Cl O NaCN in ethanol H+(acid) OH C O Cl or base, then acid
H+/H2O C O dry ether Br+ Mg OH C C C OH O Pt, Pd, Ru or Ni + H2 25 C C C OH O Pt, Pd, Ru or Ni + H2 25 C C C H H
OH O H+/H2O Mg + dry ether C C Br O H+/H2O Mg dry ether C + 2 Br O OH C + OH OH O Li H+/H2O + dry ether C C
H+/H2O C O dry ether Br+ Mg OH C C C OH O Pt, Pd, Ru or Ni + H2 25 C C C OH O Pt, Pd, Ru or Ni + H2 25 C C C H H
O Mg/ dry ether Br H+/H2O OH H Dry ether AlCl3 neat O O N2H4/OH- Cl Reaction name ? or Zn-Hg/HCl heat Reaction name ? Wolff-Kishner reduction Clemmensen reduction KOH In ethanol What s my name? NBS/light styrene
Cu Li O Cl O Name of this reaction ? Corey-House reaction Cl Li(Al-tBuO)3 In ether or neat H O O SOCl2/pyridine or PCl3 neat H O Cl O O
NaBH4 methanol, then H2O OH O Supply a moderately strong reducing agent/solvent different than H2 that does these two conversions C C NaBH4 methanol, then H2O OH O C C H H LiAlH4 In ether, then H2O Supply a strong reducing agent/solvent different than NaBH4 that does these two conversions OH O C C LiAlH4 In ether, then H2O OH O C C H H
O Mg/ dry ether Br H+/H2O OH H Dry ether AlCl3 neat O O N2H4/OH- Cl Reaction name ? or Zn-Hg/HCl heat Reaction name ? Wolff-Kishner reduction Clemmensen reduction KOH In ethanol What s my name? NBS/light styrene
Name the three major of diene addition reactions 1)Addition of HX 2)Addition of X2 3)Addition of dienophiles Addition of dienophiles go by at least 3 different names. What are they ? 1,3-cycloaddition 2+4 cycloaddition Diels-Alder reaction heat + A reaction condition Who is the dienophile above ?
Aromatic-aliphatic and synthesis drill and practice (cont.) Industrial route to styrene ??? ZnO/60 oC Order the reactivity of Br below from highest to lowest reactivity Br A B Br C Br A > C >B Cl AlCl3 H + C 3 Cl Cl neat H
O H O O Br Br PBr3/Br2 H2O C C C OH H OH Br H H Example of Hell-Volhard-Zellinsky reaction ( not quite aldehyde or ketone but similar) H H3 C + CH2 H3C NaOH C H H H O H3C CH2 CH3 then neat C H3C C H H H O H C OH H H3 =2 C CH2 O H H O O H +H2O Reaction name ? (You did one in lab ) Aldol condensation (aldehyde to bigger alcohol alkene) bigger
O O HIO4 2 H O KMnO4 Ar- P Ar- O + Ar- H2 O Main product O + + NH3 NH H2O By- product
Route to peroxy acid + O H O OH H O O H O O O + O O + H O O H O O O Name of the above oxidation ? Baeyer-Villiger By-product Product Ar Ar Ar benzene HCl P + + C Cl C P Ar Ar H Ar Weird name of product ylide Product By-product
HBr, H2SO4 reflux Br OH Old school, classic route PBr3(g) Br OH Neat, with bubbling New school, modern route 1 SOBr2 Br OH in pyridine or KHCO3(aq) New school, modern route 2
H+ NaCN O COOH CH3CO-OOH O O O (methyl peroxy acid) OH H 2 H KOH H O O
http://introvertspring.com/wp-content/uploads/2014/08/Cat-Hiding-Under-Blanket.jpghttp://introvertspring.com/wp-content/uploads/2014/08/Cat-Hiding-Under-Blanket.jpg Organic Chemistry makes me want to hide all day under a blanket .
