Organic Exam 3

KMn04—>-OH (Cold)

Requires a double bond. The Double bond tuns into an OH that connects to each end.

 

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KMn04—>H+ (Heat)

 

Turns the double bonds into two seperate carboxylic acids. They appear on each side of the double bond. 

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O3—>Zn,H20 (or Me2S)

This is a workup reaction from our last exam. You have to break the double bond and form a double bonded oxygen at each end of the broken bonds. 

 

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This reaction is very similar for another example. They both do the same thing.

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O3—->H2O2

Another workup reaction. Instead, this actually turns an available H into an alcohol. (pg) 155

 

 

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PCC

1 degree- aldehyed

2 degree- keytone

3 degree- alcohol

Look at the top picture. (Pg 155)

 

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K2Cr2O7/H2SO4

Cro3/H2SO4

Kmn04,Oh-

Kmno4,H+

 These are all strong oxidizers. There is a great picture on page 155 of our notes. 

1 degree-Carboxylic Acid

2 degree- Keytones

3-remains and alcohol

aldehyde to C02H

 

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Ag2O,NH3

Br2,H20

A mild oxidation of aldehydes. This turns an aldehyde into a carboxylic acid. (Pg 155)

 

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KMnO4/OH-,Heat—–>H30+

This reaction turns  any R group into a Carboxcylic acid. Remember, there must be a Hydrogen available in the Benzyllic position or else this reaction would be “No Reaction” (Pg 156).

 

A great page is dedicated to this reaction on page 156.

 

1)X2, NaOH

2)H3O+

 

 

 

Where X is either Cl,Br, or I

From page 156, This reaction turns a keytone into a carboxcylic acid and the second product would be CHX3.

 

A great example is on page 156. 

1) NaCN

2) H2O,H3O+,Heat

1) Removes the best leaving group and replaces it with a CN.

2) Turns the CN into a carboxcylic acid.

(Page 157)

*Beware of the keytone.

 

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1)H20,OH-(excess)

Heat

2)H30+

This reaction will remove the best leaving group, leaving you with a partially negative O2. Finally, the H30+ comes in and turns the CO2- into a carboxylic acid.

 

Check out page 157 at the very bottom of the page.

Grignard Reaction

1)X2, Fe

2) Mg,ether

3)Co2, H30+

This reaction will initally place your X group onto the benzene ring. The 2nd step will place an Mg in front of the X group. The CO2 will replace the MgX and finally, the H3O+ will turn the CO2- into a carboxcylic acid. (Page 158)

 

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SOCL2 or PCL3

Will turn an Alcohol into a Cl group. 

 

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Heat( 500-700) Degrees C.

Pg 160 *also page 165

Will actually form an anhydride, which looks like the image below. 

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In addition, look on page 68 on the practice exams for a great example of how this reaction can be used.

HO-R

H+

 

The H+ will act as a catalyst. The best leaving group will be removed and the O-R group will occupt its place. 

 

Look on page 160 for a great example.

H—NR2

Heat

This reaction will add an amine group by replacing the leaving group.

 

Check out page 160 for more details

Order of Reactivity

 

 

RCOCl,RCOOCOR,RCOOR, and RCONR2

The order will be described on page 161 in the notes.

They are in order as seen above. 

PCl5

Very similar to PCl3 or SOCl2, this will remove the best leavign group and replace it with a Cl group. (Page 164)

 

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Mirgatory Aptitude

 

What is the Order from fastest to slowest?

 

H>Phenyl>3*Alkyl>2*Alkyl>1*Alkyl>Methyl

 

CH3COOOH

This reaction will add an Oxygen to the place of FASTEST Migratory Aptitude. By memorizing the 6 placements, you will be able to understand this reaction easily. remember to look at the Alpha Carbons.

 

Great examples are on page 174

1) X2,P

2)H20

 

 

X=Cl or Br

This reaction will remove an available Alpha H and add the X group in its place. This is an intersting reacion because on the page of the notes,(175) the CO2H remains unaffected. However, from page 68 on the old exams, the CO2H actually turned into a CO2Br. Things that make you go Hmmmmmm…

1)K2CO3

2) H20,Heat

This reaction will turn the X group into an OH group, and deprotenate a H off an alcohol.

(Page 175) Notes

 

NH3

This reaction will Turn the X group into an NH3 as well as deprotenates the H off the alcohol group.

 

Check out Page 175 and page 63 of old exams

H2,Pd/C

Low Pressure

It actually look like it has no effect on the keytone. Look at page 178 for more information.
H2Pd/C High Pressure or NaBH4/LiAlH4 H20

This reaction will transform a keytone into an an alcohol. Page 178 shows a great example of how these reactions can do the exact same thing. 

 

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1)HOCH2CH2OH/H+

2)LiAlH4

3)H30+

Or

LiALH4(Excess)

H2O

This is a reducing agent that will Turn a Carboxcylic acid into two seperate Alcohol groups. Look on page 178 for an example. The only difference is that the LiAlH4 will actually turn the Keytone into an Alcohol as well.
H2O Or CH3OH

This reaction will deprotenate the available electrons off of the Nitrogen and add the hydrogen. This then sends two availbale electrons to the Bromine. In Addition, the X group will become a partial negative group. 

 

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H2/Raney Ni (Pressure/Heat)

Or

LiBH3CN

Turns a double bonded oxygen into a double bonded NH. Look at page 190. Though it is coupled with NH3, I wrote in the reaction for just what he stated in class.

HONO2

H2SO4

This eraction will turn a Benzyllic H into a NO2. By coupling it with H, it will turn that NO2 into a NH2.

Page 192

 

 

Fe/HCl

OH-

This reaction will also turn a NO2 group into an NH2 group. Page 192 will help clear up any questions.

NaNO2

HCl,H2O

(0-5* C)

 

This reaction will react differently depending on the placement.

1*-Turns the NH2 into a double bonded N=N

2* Will yield a Nitroso derivativeN=O

3* Will actually add the N=O onto the N group; thus making the N +.

Page 194

NaNO2

HCl

This reaction will turn a NH2 group into a triple bonded N=-N Group. Check out page 198.
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