Quiz 3. Flashcards
How do you add NO2 to benzene?
React benzene with HNO3 and H2SO4.
What is a diazonium compound?
A benzene ring that is bonded to a positive N which has a triple bond to another N.
How do we turn the Benzene bonded to NO2 into a diazonium compound?
React the benzene bonded to NO2 with NaNO2 and HCl.
How reactive are diazonium compounds?
Diazonium compounds are very reactive.
If K-I is reacted with a diazonium compound, what is the product?
A benzene ring bonded to an iodine.
If Cu-Br is reacted with a diazonium compound, what is the product?
A benzene ring bonded to an bromine.
If Cu-Cl is reacted with a diazonium compound, what is the product?
A benzene ring bonded to a chlorine.
If a phenol is reacted with a diazonium compound, what is the product?
Benzene-N=N-Benzene-OH.
If H3-P-O2 or Et-O-H is reacted with a diazonium compound, what is the product?
Benzene.
If H2O and H2SO4 at 100 degrees C is reacted with a diazonium compound, what is the product?
A phenol.
If Cu-C-N is reacted with a diazonium compound, what is the product?
A benzene bonded to a C-N
If H-B-F4 is reacted with a diazonium compound, what is the product?
A benzene bonded to a fluorine.
What are activators?
This is more likely to react than a benzene ring.
What are deactivators?
This is less likely to react than a benzene ring.
What are the activating groups?
What are the deactivating groups?
What are the ortho, para and meta substitution positions?
What are the ortho, para directing groups?
What are the meta directing groups?
What are the 3 steps to determining whether something is ortho, para or meta directing?
Look at all the substituents separately. Determine if its ortho, para or meta directing. Determine where addition goes.
What electrophile is used for the bromination of benzene?
Br2 + Fe-Br3 = Br-Br+-Fe(-)-Br3.
What electrophile is used for the chlorination of benzene?
AlCl3 or FeCl3 + Cl2 = Cl-Cl+-Al(-)-Cl3.
What electrophile is used for the iodination of benzene?
HNO3 + H+ +1/2 I2 = I+ + NO2 + H2O.
What electrophile is used for the nitration of benzene?
HNO3 + H2SO4 = A benzene ring bonded to NO2 + H2O.
What electrophile is used for the sulfonation of benzene?
Benzene + SO3 (electrophile) + H2SO4 = Benzene bonded to SO3H.
What is the Friedel Crafts reaction used for?
The Friedel Crafts reaction is used to turn benzene into a benzene with a hydrocarbon chain attached.
What is the electrophile in the Friedel Crafts reaction?
R-CH2 + -Cl+Al(-)-Cl3.
What are the steps of the Friedel Crafts reaction?
Electrophile is formed. Benzene ring attacks C+ and the Cl leaves. The aromaticity on the benzene ring is lost. To regain the aromaticity the chlorine comes back and removes the H thats bonded to the same C as the new hydrocarbon group. The double bond reforms and aromaticity is restored.
Can rearrangements happen in the Friedel Crafts reaction?
Yes.
What are benzylic hydrogens?
The hydrogens that are on the chain carbons that are attached to the benzene.
Which hydrogens does NBS or Br2 attack?
The benzylic hydrogens.
Which hydrogens doNBS or Br2 for attack?
Benzylic hydrogens close to the benzene ring.
If you react HNO3 with H2SO4 and a benzene ring, what products are formed?
A benzene ring with NO2 attached.
What does NBS look like?
What is aniline?
Is aniline ortho, para or meta directing?
Ortho, para.
What wavelength, region, energy KJ/mol and molecular effects of gamma rays?
Wavelength = 10 to the -9. Energy = 10 to the 7. Molecular effects = ionisation.
What wavelength, region, energy KJ/mol and molecular effects of X rays?
Wavelength = 10 to the -7. Energy = 10 to the 5. Molecular effects = ionisation.
What wavelength, region, energy KJ/mol and molecular effects of vacuum UV?
Wavelength = 10 to the -5. Energy = 10 to the 3. Molecular effects = electronic transitions.
What wavelength, region, energy KJ/mol and molecular effects of near UV?
Wavelength = 10 to the -5. Energy = 10 to the 2. Molecular effects = electronic transitions.
What wavelength, region, energy KJ/mol and molecular effects of visible UV?
Wavelength = 10 to the -4. Energy = 10 to the 2. Molecular effects = molecular vibrations.
What wavelength, region, energy KJ/mol and molecular effects of infrared?
Wavelength = 10 to the -3. Energy = 10. Molecular effects = molecular vibrations.
What wavelength, region, energy KJ/mol and molecular effects of microwave?
Wavelength = 10 to the -1. Energy = 10 to the -1 up to 1. Molecular effects = rotational motion.
What wavelength, region, energy KJ/mol and molecular effects of radio?
Wavelength = 10 to the 4 up to 10 to the 2. Energy = 10 to the -6 up to 10 to the -2. Molecular effects = nuclear spin transitions.
Is cyanide a good nucleophile?
Yes.
What is Cyanide?
How do you turn an alkyl halide into an amine?
When you turn an alkyl halide into an amine, by how much does the carbon chain increase?
By 1 carbon.
What reaction is used to turn an amide into an amine?
The Hoffman rearrangement.
What is an amine?
What is an amide?
The Hoffman rearrangement is used for what kind of amides?
Primary amides.
What is the mechanism of the Hoffman rearrangement?
What is the speed of light?
3 x 10 to the 10 cm/sec.
What is an acid or acyl chloride?
How do you turn an acid chloride into an amine?
Acid chloride + ammonia. Cl is knocked off acid chloride and the amide is formed. LiAlH4 then removed the oxygen.
What is the mechanism of the formation of an amine from an acid chloride?
What is the finger print region?
No Z molecules give the same IR spectrum.
What region is the finger print region?
600 - 1400 cm to the minus 1. The region between 1600–3500 cm-1 has the most common vibrations and we can use it to get information about specific functional groups in the molecule.
Describe the IR spectrum for alcohols?
What is the IR spectrum for amides?
Describe the IR spectrum for amides?
Amides will show a strong absorption for the C═O at 1630–1660 cm-1. If there are hydrogens attached to the nitrogen of the amide, there will N—H absorptions at around 3300 cm-1.
What is the IR spectrum for carboxylic acids?
PICTURE!!!
Describe the IR spectrum for carboxylic acids?
What is the IR spectrum for ketones?
Describe the IR spectrum for ketones?
The spectrum of 2-heptanone shows a strong, sharp absorption at 1718 cm-1 due to the C═O stretch.
What is the IR spectrum for aldehydes?
Describe the IR spectrum for aldehydes?
Aldehydes have the C═O stretch at around 1710 cm-1. They also have two different stretch bands for the aldehyde C—H bond at 2720 and 2820 cm-1.
