ORGO FINAL REACTIONS

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Dilute H2SO4

adds an OH to most sub carbon, H to least sub carbon alkene

Concentrated H2SO4

acts as a dehydrating agent, converting alcohols to alkenes and facilitating elimination reactions.

HBr

hydrohalogenation: adds an Br to most substituted carbon and H to least substituted carbon

Cl2 / Br2 , cold and dark

halogenation: adds a halogen atom to each carbon of the double bond in alkenes - TRANS

NaOCH2CH3 or NaOCH2(CH3)2

often used as a strong base to deprotonate alcohols or facilitate elimination reactions and alkene formation

peroxyacetic acid

is a peracid used in organic synthesis of an epoxide ring on alkenes or aldehydes - CIS branches

O3 + H2O Zn

ozonolysis - slice, slide slap - slice alkene in half and slide products/cyclo apart, slap on a carbonyl compound on end

NaOCH3, HOCH3 epoxidation

OH on most sub, ether on least sub

HOCH3 + H2SO4 acid catalyzed epoxidation

OH on least sub, ether on most sub

H2O + H2SO4 hydro acid cat

OH on each alkene carbon, place in TRANS position, maintian og stereobonds

carbonyl + NaBH4 reduction

=O to OH, H on same carbon as OH

excess H2, metal cat redcution

=O to OH, J on same carbon as alcohol, ALL alkenes are hydrogenated and reduced to only alkanes

MgBr, H2O reduction

=O to OH, MgBr branch bonds to same carbon as carbonyl making ketone

LAH / LAD reduction + Aqueous workup

H/D on carbonyl carbon, O to =O

Chromic Acid + Aqueous Acid on primary alcohol

OH to =O

Chromic Acid + Aqueous Acid + PCC on primary alcohol

carbonyl restoration

Chromic Acid + Aqueous Acid on secondary alcohol

ketone

OsO4

CIS diol formation on alkene

HIO4

CIS vicinal diol formation, cuts cyclo into chain or cuts chain into two prods, adds an oxygenated carbonyl group at each end

alkyl bromide → alkyne

remove Br with KOH, add 2 halides w Br2 or Cl2, double elimination with 3NaNH2, NH3

PBr

primary alcohol → primary alkyl bromide

H2SO4 + HgSO4 (alkyne reduction)

removes alkyne and adds carbonyl O to where it was

alkyne + 1 eq Br2

alkyne → alkene, Br on each end of alkene

alkyne + 2 eq Br2

alkyne → alkane, 2 Br’s on each end of alkene

alkyne + 2 eq HCl →

adds 2 chlorine to the same carbon, alkyne → alkane

alkyne + HI

I added to most sub, H added to least sub, alkyne → alkene

Tautaumorize

en-ol forms first, then isolates into a carbonyl group with no alkene formation

H2 on alkyne

completely removes alkyne

2Na, 2NH3

alkyne → alkene

H2 + Lindlar

alkyne → CIS alkene