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Orgo 2 > Reaction mechanisms > Flashcards

Reaction mechanisms Flashcards

1
Q

Starting: Alcohol

(COCl)2 in DMSO?

AKA?

A

Alcohols to aldehydes and keytones.

Swern

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2
Q

Starting: Alcohol

[CrO3Cl-] + [C5H5NH+] in CH2Cl2

AKA?

A

Alcohols to aldehydes and keytones

AKA PCC

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3
Q

Starting: Alcohol

PBr3

A

Alcohol to bromine

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4
Q

Starting: Alcohol

SOCl2 with pyridine?

A

Alchohol to chlorine

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5
Q

Starting: Alcohol

ZnCl2 in HCl

A

Alcohol to chlorine

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6
Q

Starting: Alcohol

LiCl in DMF

A

Chlorine via SN2 - inversion!

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7
Q

Starting: Alcohol

MsCl, TsCl, or TfCl

A

Sulfonate ester; makes excellent LG

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8
Q

Starting: Alcohol

t-BDMS-Cl in NEt3

A

tert-butyldimethylsilylchloride; protection

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9
Q

Starting: Alcohol

KMnO4

A

Carboxylic acid on terminal alcohols or carbonyl group for all other alcohols.

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10
Q

Starting: alcohol

Cr6 in acetone

A

Carboxylic acid on terminal alcohols or carbonyl group for all other alcohols.

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11
Q

m-CPBA in CH2Cl2

A

epoxidation of alkenes (non-terminal alkenes!!)

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12
Q

Starting with an ester:

NaBH4 with MeOH

A

No reaction - too weak against esters

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13
Q

Starting with a keytone or an aldehyde:

NaBH4 with MeOH

Where do the protons come from?

A

alcohol

Alcohol = sodium borohydride
Hydrogenated carbons = methanol

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14
Q

Starting with an aldehyde or keytone:

LiAlH4

Where do the protons come from?

A

alcohol.

Alcohol = protic solvent (H2O, H3O+, etc)
On hydrogenated carbons = lithium aluminum hydrides

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15
Q

Starting with an ester or carboxylic acid:

LiAlH4

Where do the protons come from?

A

One alcohol (terminal alcohol on carboxylic acid is lost)

Alcohol = protic solvent (H2O, H3O+, etc)
On hydrogenated carbons = lithium aluminum hydrides

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16
Q

Starting with an ester:

  1. R-MgBr
  2. Acid (H3O+)

Aka?

A

Alcohol with two R groups

Grignard reagents

17
Q

Starting with an ester or a keytone:

  1. R-MgBr
  2. Acid

Aka?

A

An alcohol and one R group

Grignard

18
Q

Starting with an ester:

  1. Li-R
  2. acid
A

Alcohol and two R groups

19
Q

Starting with an aldehyde:

  1. Li-R
  2. Acid
A

Alcohol with one R group

20
Q

Ethers can be cleaved with?

A

HI or HBr (HCl and HF are too weak)

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