Organic Chemistry 1 Reagents

hydrogenation

H2, Pt/Ni/Pd, adds H to both carbons of an alkene or alkyne, reducing it to an alkane or alkene depending on starting material.

alkyne/alkene reduction

H2(g),Ni/Pd/Pe

hydrohalogenation (Markovnikov)

HX, CCl4, add halogen to more substitued carbon

hydrohalogenation (anti-Markovnikov)

HX, ROOR, Adds Br to the less substituted carbon and H to the more substituted carbon

halogenation

X2, CCl4, Adds one halogen to each alkene carbon with anti addition

halohydrin formation

X2, ROH

Markovnikov, anti-addition of OH and X

halohydrin formation (ether)

X2, ROH, Adds OR to the more substituted carbon and X to the less substituted carbon, with anti addition

acid-catalyzed hydration

H2SO4, H2O, Adds H to the less substituted carbon and OH to the more substituted carbon

Oxymercuration-Demercuration

1) Hg(OAc)2, H2O

2) NaBH4

Markovnikov hydration without rearrangement

Alkoxymercuration-Demercuration

1) Hg(OAc)2, ROH

2) NaBH4

Adds OR to the more substituted carbon and H to the less substituted carbon

Hydroboration-Oxidation

1. BH3, THF

2. H2O2, NaOH

Adds H to the more substituted carbon and OH to the less substituted carbon; overall anti-Markovnikov

epoxidation

mCPBA, adds O to make a triangle

Oxidative Cleavage

KMnO4, heat, or O3

Cuts the double bond and turns the alkene carbons into carbonyl-containing (C=O) products

Ozonolysis

1) O3, CH2CL2, -78C

2) DMS

Cleaves the alkene into aldehydes/ketones depending on substitution

CH3ONa, heat

E2

Alkene formed with X removal

SOCl2

replaces OH with Cl

HBr, ROOR, light

adds H to most substituted C

adds Br to most accessible C

HBr (only)

adds H to less substituted C

adds Br to most substituted C

X2 (only)

X added to each side of broken alkene

NBS

N-bromosuccinimide

adds Br to C ADJACENT to alkene=

KMnO4 (cold, dilute)

dihydroxylation

syn- addition

adds OH to both alkene carbons on the same face

OsO4, NaHSO3, H2O

syn dihydroxylation

CH2I2, Zn(Cu)

alkene to cyclopropane

PBr3

molecule that replaces OH with Br in an Sn2 reaction

SOCl2, base

replaces OH with Cl

HA, heat

primary alcohol ---> ether, two alcohol molecules can lose water overall and form an ether under acidic conditions, especially with primary alcohols

OTs, OMs, OTf

Williamson ether synthesis

R-O-R'

asymmetrical

HBr/ROOR (peroxide)

radical reaction

Br added to terminal end of alkene =

Br2, light

Radical Mechanism

Forms most stable intermediate

What is being removed: a hydrogen from the alkane.

What is being added: bromine in its place.

reducing agents

NaBH4 (mild)

A reducing agent that adds hydride, H⁻, to carbonyls.

What is being added: hydride.

What is being removed: the carbonyl oxygen’s double-bond character

LiAlH4 (strong)

Also adds hydride, but is strong enough to reduce more functional groups.

What is being added: hydride.

What is being removed: the oxygen-based functionality being reduced

NaBH4, H20

aldehyde--->primary OH

ketone---> secondary OH

What is being added: hydride and then proton

What is being removed: the C=O double bond

LiAlH4, H3O+

Carboxylic acid---> primary alcohol (directly)

What is being added: hydride, then proton.

What is being removed: the carboxylic acid oxygen arrangement.

DIBAL-H

-Reduces esters to aldehydes

-aldehyde--->alcohol

-ketone---> alcohol

What is being added: hydride.

What is being removed: some or all of the carbonyl oxygen character, depending on substrate and conditions

MgBr, H3O+

Grignard

*adds as many Cs attached to MgBr

The Grignard reagent behaves like R⁻, so it adds a carbon group to an electrophile.

What is being added: a carbon chain from the Grignard reagent.

What is being removed: the electrophile’s carbonyl or leaving-group structure, depending on the substrate.

Mg, EtO2

attaches Mg to Br

PCC

oxidation of primary alcohol--->aldehyde

or secondary alcohol--->ketone

What is being added: oxygen functionality in the sense of increased oxidation state.

What is being removed: hydrogens from the alcohol carbon.

NaOH

strong base

CrO3, H3O+

primary alcohol---> carboxylic acid

What is being added: more oxygen and higher oxidation state.

What is being removed: hydrogens from the alcohol carbon.

NaH, CH3I

OH---> OCH3

Grignard + epoxide

The Grignard opens the epoxide ring.

What is being added: the carbon group from the Grignard plus an OH after workup.

What is being removed: the strained epoxide ring.