reactions of alkenes + alkynes + light reactions

BH₃ ∙ THF
_____________>
H₂O₂, NaOH

generates products where the OH group is on the less substituted side of the double bond, while the H is on the more (anti-markovnikov addition)

H₂, Pt →

generates products where the alkene converts to an alkane, (make sure to check for chiral centers tho)

CH₃CO₃H/RCO₃H, H3O⁺ →

generates products where the OH are added to the double bond in an anti conformation to each other

OsO₄, NaHSO₃/H₂O

generates products where the OH groups are added in a syn conformation to each other

H₃O⁺→

generates products where the OH group adds to the more substituted side of the double bond while the H adds to the less, but generates carbocation intermediates and rearrangements.

HBr→

Generates products where the Br adds to the more substituted side of the double bond and the H adds to the less, (Markovnikov addition)

1)Hg(OAc)₂, H₂O
2)NaBH₄

Oxymercuration- Demercuration. Adds 1 OH group in an markovnikov addition across a double bond. The H2O can be switched out with other nucleophiles too.

HBr, ROOR →

creates products where bromine is added to the less substituted end of the double bond.

Br₂, H₂O

forms products with a Br on the less substituted end and a OH group on the more substituted end.

Br₂

forms a ring and then is broken by another bromine, causing an addition of two bromines in an anti configuration across a double bond.

1) O₃
2) NMO

forms products where an oxygen is added to both sides of each double bond of the reagent.

KMnO₄, NaOH, cold

generates products where the OH groups are added in a syn conformation to each other

1) mCPBA
2) H₃O⁺

forms products that add OH groups in an anti-conformation across a double bond through epoxide ring formation.

H₂ (lindlars cat)

generates products where the triple bond of an alkyne is converted to a cis double bond alkene

H₂, Ni₂B

generates products where the triple bond of an alkyne is converted to a cis double bond alkene

Na in (NH₃) (l)

generates products where the triple bond of an alkyne is converted to a trans double bond alkene

HX (one equivalent) in alkynes

creates a double-bonded carbon (alkene) with the halogen on the more substituted side

1)HgSo₄
2)H₂SO₄, H₂O of an alkyne

creates a double-bonded oxygen (ketone) that was tautomerized

1) disiamylborane 2) H₂O₂, NaOH

creates a product where the OH group adds the less substituted portion of the alkyne and tautomerizes into an aldehyde.

1) 9-BBN
2) H₂O₂, NaOH

creates a product where the OH group adds the less substituted portion of the alkyne and tautomerizes into an aldehyde.

1) R₂BH
2)H₂O₂, NaOH

creates a product where the OH group adds the less substituted portion of the alkyne and tautomerizes into an aldehyde.

1) O₃
2) H₂O

creates an alkene where the R group is attached to a ketone and an OH group, unless the alkyne has a terminal carbon in which it will become CO2

Acetylene

triple bonded carbon

Br₂, hu (light)

addition of a Bromine atom to the more substituted position of an alkane. Has a radical intermediate where Br replaces one of the hydrogen atoms on an alkane.

NBS, hu (light)

Allylic bromination on a carbon that is attached to another C=C. Adds Br in place of one of the hydrogens on the Allylic carbon

Is HBr a radical addition process?

yes

reduction =

increase in C-H bonds

oxidation =

increase in C-O

NaBH₄, (MeOH, H2O or EtOH)

makes a double-bonded oxygen into an alcohol group through the nucleophilic attack of a hydrogen bond. Powerful enough to reduce ketones and aldehydes.

1. LiAlH₄ (aka LAH)
2. H3O+ workup

much more reactive, 2 steps that result in a double bonded oxygen of an aldehyde or ketone turning into an alcohol. Can also reduce esters and carboxylic acids if there is excess (process happens twice in this case)

grignard reagent

creates a source of nucleophilic carbon. Mg atom is added between a Br to make the carbon bond more nucleophilic. Can be used on aldehydes, ketones and esters to add a carbon bond and reduce a double bond to an alcohol.

POCl3

gets rid of an alcohol group and adds a double bond to the more substituted end.

PCC

adds a double bond to an alcohol

PBr₃

adds a Br to the position of the original alcohol

SOCl2 + pyridine

adds a chlorine to an alcohol position