Alcohol Reactants, Epoxide Reactants, Ether Reactants

alcohol + metal hydride

forms an alkoxide

alcohol + active metal

forms an alkoxide

alcohol + H[halogen]

substitution reaction that forms an R-[halogen] and water

alcohol + PBr3, pyridine

substitution reaction that forms an alkane bromide by replacing -OH with -Br
CH3OH (1', 2' Alcohol only) as well as POBR2 and other salts

alcohol + SOCL2

substitution reaction that generates an alkyl chloride

alcohol + MsCl, pyridine

substitution reaction that converts R-OH to a sulfonate; forms an alkyl nucleophile and OMs-

alcohol + TsCl, pyridine

substitution reaction that converts R-OH to a sulfonate; forms an alkyl nucleophile and OTs-

alcohol + strong acid, heat

dehydrating elimination reaction that generates an alkene

alcohol + H2SO4, heat

dehydrating elimination reaction that generates an alkene

alcohol + H3PO4, heat

dehydrating elimination reaction that generates an alkene

alcohol + CrO3, H2SO4, Δ

Jones Oxidation reaction that results in a C=O in the form of an aldehyde or, if H2O is present, a carboxylic acid (1°) or in the form of a ketone (2°)

alcohol + Na2Cr2O7, H2SO4, Δ

Jones Oxidation reaction that results in a C=O in the form of an aldehyde or, if H2O is present, a carboxylic acid (1°) or in the form of a ketone (2°)

alcohol + K2Cr2O7, H2SO4, Δ

Jones Oxidation reaction that results in a C=O in the form of an aldehyde or, if H2O is present, a carboxylic acid (1°) or in the form of a ketone (2°)

alcohol + PCC

oxidation reaction that turns 1° alcohols into aldehydes and 2° into ketones

alcohol + (1) (COCL)2, DMSO (2) Et3N

Swern Oxidation reaction that turns 1° alcohols into aldehydes and 2° into ketones

alcohol + (1) DMP, (2) Et3N

DMP Oxidation reaction that that turns 1° alcohols into aldehydes and 2° into ketones

alcohol + HIO4 (periodic acid)

Periodic Acid oxidation reaction that splits C-C bond and replaces it with a O=C bond by splitting the reactant

structure of PCC

structure of mesyl chloride (CH3SO2Cl)

structure of DMP

structure of oxalyl chloride/(COCL)2

structure of Et3N

structure of pyridine

structure of a metal hydride

compounds of one or more metal cations (M+) and one or more hydride anions (H−)

structure of halohydrin

a halogen and a hydroxyl are bonded to adjacent carbon atoms

structure of PBR3

structure of H2SO4

structure of H3PO4

alkene + mCPBA

syn epoxide synthesis stereospecific rxn that generates an epoxide and a carboxylic acid

alkene + [R]CO3H

epoxide synthesis stereospecific rxn that generates a racemic mix of enatiomers

alkane + halohydrin

forms an alkoxide used to generate epoxide

structure of an alkoxide

an organic group bonded to a negatively charged oxygen atom, written as RO− and often ionically bonded to a positively charged ion (like Na+)

structure of an epoxide

organic three-membered cyclic oxygen compounds

structure of a halohydrin

a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms

alkene + halogen, H2O

forms a halohydrin (with an OH group) to generate an alkoxide which helps generate an epoxide

epoxide + strong acid (H+), H2O

acid catalyzed ring opening rxn in which the acid attacks the more substituted carbon

structure of H2SO4

very strong acid

epoxide + strong base (OH-), H2O

base catalyzed ring opening rxn in which the strong nucleophile attacks the less substituted carbon

epoxide + alkoxide, alcohol

ring opening rxn that acts as a fully SN2 rxn

epoxide + H+, alcohol

ring opening rxn that acts as an "SN1-like" SN2 rxn

epoxide + strong nucleophile (no acid)

ring opening rxn that generates an alkyl with an alcohol group from the nucleophile attacking the less substituted carbon

alcohol + H+, Δ, low heat

ether synthesis reaction that works with symmetrical ethers by adding the R groups on either side of the O

alkyl halide + alkoxide

Williamson Ether Synthesis that results in asymmetrical ethers

structure of an alkoxide

consists of an organic group bonded to a negatively charged oxygen atom and tends to form ionic bonds with positive ions, like Na+

ether + HI or HBr (1 eq.)

ether cleavage resulting in an alkyl halide and an alcohol; uses SN1 unless both Cs are 1°

structure of an ether

R-O-R

ether + HI or HBr (2+ eq.)

ether cleavage resulting in an alkyl iodide or alkyl bromide and alcohol; uses SN1 unless both Cs are 1°

structure of an alkyl halide

alkyl group bonded to a halogen

alkene + acid (H+), R-OH

acid catalyzed addition of alkenes to alcohols and ethers