Reactions w/ Reagents

HX (alkene)

adds X + H; carbocation intermediate

dilute H2SO4 & H2O (alkene)

adds H + OH; carbocation intermediate

cat. H2SO4 & ROH (alkene)

adds H + OR; carbocation intermediate

1. Hg(OAc)2 & H2O

2. NaBH4

(alkene)

adds H + OH; 3 membered ring w/ Mercury

Cl2 & CCl4 (alkene)

adds X + X; anti-addition

X2 & H2O (alkene)

adds X + OH; 3 membered ring w/ halogen

1. mCPBA

2. cat. H2SO4 & H2O

(alkene)

adds OH + OH; anti-addition; forms epoxide

1. OsO4

2. NaHSO3 & H2O, NMO

(alkene)

adds OH + OH; syn addition

1. BH3 x THF

2. NaOH, H2O2, H2O

(alkene)

adds H + OH; syn and anti-Markovnikov

H2 & Pt/Pd/Ni (solid metal) (alkene)

adds H + H; syn addition

HBr & ROOR (alkene)

adds H + Br; anti-Markovnikov

1. O3

2. S(CH3)2

(alkene)

makes 2 aldehydes/ketones

1. xs NaNH2

2. H2O

(alkane)

creates alkyne

1. xs NaNH2

2. xs CH3I

(alkyne)

makes C-C bond on alkyne

1. O3

2. H2O

(alkyne)

creates carboxylic acid

H2 & Pd (alkyne)

creates alkane (adds H’s)

H2 & Lindlar’s Catalyst (alkyne)

creates cis alkene

Na^o & NH3

creates trans alkene

? eq. HBR (alkyne)

adds H + Br; Markovnikov [depending on how many equivalents: 1 = alkene 2 = alkane]

? eq. HBr & ROOR (alkyne)

adds H + Br; anti-Markovnikov [depending on equivalents; 1 = alkene 2 = alkane]

? eq. Cl2 (alkyne)

adds Cl + Cl; anti-addition trans [depending on equivalents; 1 = two Cls 2 = four Cls]

NBS; hv

adds Br with Radical

HgSO4, H2SO4, H2O

adds C=O on alkyne to more substituted C

1. 9-BBN

2. NaOH, H2O2, H2O

adds C=O on alkyne to less substituted C