ch 9 alcohol ethers and epoxides reagents

how to Convert Hydroxyl Groups into Good Leaving Groups?

convert alcohol to alkyl halide (HI, HBr, HCl) 

when Converting Hydroxyl Groups into Good Leaving Groups, what reaction do primary, secondary and tertiary alcohol undergo?

primary alcohol: SN2

secondary and tertiary alcohol: SN1

primary or secondary alcohol + 1) PBr3, pyridine 2) NaN3? does it cause conversion?

alkyl bromide, yes to conversion

primary or secondary alcohol + 1) PBr3, pyridine 2) NaN3 3) CN-? does it cause conversion?

SN2 reaction, yes to inversion

primary or secondary alcohol + 1) SOCl2, pyridine 2) NaN3? does it cause conversion?

alkyl chloride, yes to inversion

primary or secondary alcohol + 1) SOCl2, pyridine 2) NaN3 3) CN-? does it cause conversion?

SN2 reaction, yes to inversion

primary or secondary alcohol + 1) MsCl, pyridine 2) NaN3? does it cause conversion?

tosylate, no inversion

primary or secondary alcohol + 1) MsCl, pyridine 2) NaN3 3) CN-? does it cause conversion?

SN2, yes inversion

primary or secondary alcohol + 1) TsCl, pyridine 2) NaN3? does it cause conversion?

mesylate, no inversion

primary or secondary alcohol + 1) TsCl, pyridine 2) NaN3 3) CN-? does it cause conversion?

SN2, yes inversion

Williamson Ether Synthesis reagents

alcohol +

1) NaH or NaNH2 (strong base)

2) alkyl halide

alcohol + 1) NaH or NaNH2 (strong base) 2) alkyl halide

ether

Ether Synthesis reagents

1) acid catalyst

2) second molecule of the alcohol (same as starting reagent)

primary alcohol + 1) acid catalyst 2) second molecule of the alcohol (same as starting reagent)

symmetrical ether

Acidic Cleavage of Ethers can and cannot be used with what alkyl halide?

can: HBr, Hl

cannot: HCl, HF

ether + HBr

2 alkyl bromide

ether + HI

2 alkyl iodide

If the ether is bound to an aryl or vinyl group, what is produced?

alcohol (does not undergo substitution) and alkyl halide

what is an epoxide? 

three membered ring consisting of one oxygen atom and two carbon atoms

When an asymmetric epoxide is opened in basic conditions, where does the ring open?

ring opening occurs at the less substituted position (nucleophile attaches to less substituted position)

When an asymmetric epoxide is opened in acidic conditions, where does the ring open?

ring opening occurs at the more substituted position (nucleophile attaches to more substituted position)

epoxide ring opening in acidic and basic conditions cause what to the stereochemistry

inversion of stereochemistry