addition reactions

organic chemistry 1

what is Hydrohalogenation

treatment of alkene with HX (Cl, Br, I)

X added to double bond

Regioselectivity of hydrohalogenation

Markonikov

Markonikov addition

addition of a polar molecule to an asymmetric alkene, the (H) attaches to the C with more H, while the other group (such as X, OH, or OR) attaches to the C with fewer H.

anti-Markonikov addition

addition of a polar molecule to an asymmetric alkene, the (H) attaches to the C with fewer H, while the other group (such as X, OH, or OR) attaches to the C with more H.

Regioslectivity of hydrohalogenation with ROOR

anti-Markonikov

Steps of a hydrohalogenation

1. Proton transfer

2. Nucleophilic attack

Do hydrohalogenations form enantiomers

Yes - depends on carbocation formation/rearrangement

what does Acid-catalyzed hydration add

addition of OH and H

Steps for acid-catalyzed hydration

1. Proton transfer

2. nucleophilic attack

3. Proton transfer

Regiosleectivity for acid-catalyzed hydration

Markonikov

Hydrohalogenation reagents

HX

Hydrobromination reagents (anti)

HBr, ROOR

Acid-catalyzed hydration reagents

H3O+ or H2O + H2SO4

Oxymercuration-demercuration reagents

1) Hg(OAc), H2O

2) NaBH4

Hydroboration-oxidation reagents

1) BH3 - THF

2) H2O2, NaOH

Hydrogenation reagents

H2, Pt

Bromination reagents

Br2

Halohydrin formation reagents

Br2, H2O

Anti-dihydroxilation reagents

1) RCO3H

2) H3O+

Syn-dihydroxilation cold reagents

KMnO4, NaOH cold

Syn-dihydroxilation reagents

1) OsO4

2) NaHSO3, H2O

Ozonolysis reagents

1) O3

2) DMS

Hydrohalogenation adds

Halogen and H

Catalyzed Hydrogenation adds

H2

what is Halogenation

Adds 2 halogens

Steps of acid catalyzed hydration

1) Proton transfer

2) Nucleophlic attack

3) Proton transfer

How does concentration affect acid-catalyzed hydration?

The more H2O (diluted H2SO4) will favor formation of alcohol

The less H2O (conc. H2SO4) will favor the alkene

Does acid-catalyzed hydration produce enantiomers?

Yes

Regioselectivity of oxymercuration-demercuration

Markonikov

what does oxymercuration-demercuration add

OH and H

Regioselectivity of Hydrobroration-oxidation

anti-markonikov

Stereoselectivity of hydroboration-oxidation

syn-addition (same plane)

what does hydroboration-oxidation add

OH and H in a syn manner

What does catalytic hydrogenation add

2 Hydrogens

stereospecificity for catalytic hydrogenation

syn addition

Heterogeneous catalyst

Pt, Ni, Pd

What does halogenation add

2 halogens across alkene

stereospecificity of halogenation

anti-addition

what does halohydrin formation add

Halogen and OH

where does OH go in halohydrin formation

in the most substituted position

what does anti-dihydroxilation add

2 OH in anti manner

what does syn-dihydroxilation add

2 OH in a syn manner

what happens in an ozonolysis reaction

double bond is split to form two C=O

Will this base deprotonate a terminal alkyne

Yes

Will this base deprotonate terminal alkyne

yes

Will this base deprotonate a terminal alkyne

yes

will this base deprotonate a terminal alkyne

no

will this base deprotonate a terminal alkyne

no

will this base deprotonate a terminal alkyne

no

name the reaction that makes this

Hydrohalogenation (Markonikov)

name the reaction that makes this

Hydrohalogenation (Anti-Markonikov)

name the reaction that makes this

Acid-catalyzed hydration

Oxymercuration-demercuration

name the reaction that makes this

Hydroboration-oxidation

name the reaction that makes this

Hydrogenation, catalyzed hydration

name the reaction that makes this

Bromination/Halogenation

name the reaction that makes this

Halohydrin formation

name the reaction that makes this

anti-dihydroxylation

name the reaction that makes this

syn-dihydroxylation

name the reaction that makes this

ozonolysis

SN2 _____ be performed in tertiary alkyl

cannot

Regioselectivity of E2 reactions

Favor Zaitsev product

Zaitsev product definition

more substituted alkane

what is alkyl treated with for substitution

nucleophile

what is alkyl treated with for elimination

base

what is key about the configuration of a substitution reaction

it undergoes an inversion of configuration due to back side attack

What type of nucleophile is needed for SN2 reaction

strong nucleophile

Name 5 strong nucleophiles

Name 2 weak nucleophiles

Hoffman product definition

less substituted product

chemicals that are Strong Base/Strong Nucleophile

chemicals that are weak base/strong nucleophile

chemicals that are weak base/weak nucleophile

chemicals that are strong base/weak nucleophile

strong base/weal nucleophile will favor

E2

strong base/strong nucleophile will favor

SN2 and E2

weak base/strong nucleophile will favor

SN1 and SN2

weak base/weak nucleophile will favor

SN1 and E1

Catalytic hydrogenation with Lindlar-P2 catalyst

alkyne to cis alkene

Catalytic hydrogenation with H2/Pt

alkyne to trans alkane

radical anion

intermediate with both a negative charge and a unpaired electron

convert terminal alkyne to trans alkene

catalytic hydrogenation with Lindlar catalyst

convert internal alkyne into trans alkene

1) Na

2) NH3