alkene addition reaction (mostly) product prediction | Quizlet

X2 (Br2), H2O

halohydrin formation

X and OH added anti

(markovnikov: H2O attacks more substituted side of halonium ion intermed —> OH on more substituted C)

H2, Pd/Pt/Ni

hydrogenation (reduction)

H and H added syn

1. O3

2. Zn/H+/DMS

ozonolysis

aldehyde and/or ketone (cut double bond down the middle, put O on each double bond)

HX (HBr, HCl)

hydrohalogenation

H and X added

markovnikov: X to more substituted C

not stereoselective - mixture of syn and anti

H2O, acid (H+ etc)

acid-catalyzed hydration

H and OH added

markovnikov: OH to more substituted C

no regioselectivity —> mix of syn and anti

1. BH3

2. H2O2, -OH

hydroboration oxidation

H and OH added

anti-markovnikov: OH to less substituted C

X2

halogenation

X and X added anti (vicinal dihalide created)

OsO4/KMnO4 (osmonium __, potasium manganate), cold dilute -OH

dihydroxylation (mild oxidation)

OH and OH added syn

(w other reagents, can include formation of an epoxide ring, addition is anti)

SOCl2 (thionyl chloride)

R-Cl

substitutes an OH group with a Cl (SN2)

NaNH2 (sodium amide)

form alkynes (C-=C) (when u have 2 NaNH2, one for each bond)

can create triple bond from dihalides by stealing e- from both X's in a dihalide, eliminating the X's (E2)

deprotonate terminal alkynes

create acetylide anion

CrO3/H+ (H2CrO4)

chromic acid oxidation - oxidizes alcohols

primary alcohol —> carboxylic acid

secondary alcohol —> ketone

also oxidize aldehyde —> carboxylic acid

NaBH4 (sodium borohydride)

reduces aldehydes and ketones to alcohols (R-OH)

(splits the double bond to O, adds H to the O and to other single bond —> OH, H, R, R on the C)