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Organic Chemistry

Exam #3

The pi electrons of benzene are located: Above and below the ring plane.
Anthracene -It is a component of coal tar -(400-500 nm peak)
What reagents most effectively convert an aromatic compound into an unconjucated cyclohexadiene? Na in NH3(l)
What is unusual about the electrophile normally used in sulfonation of aromatic compounds? It is not a cation
Friedel-Crafts alkylation and acylation are similar but differ in one important way: Only alkylation often involves rearrangements.
There is no such substituents as one that is both __ and ___-directing. Activation; m-
Electrophilic Reagent attracted to electrons that participates in chemical reaction by accepting an electron pair in order to bond to a nucleophile. electrophiles accept electrons, they are Lewis acids Most electrophiles are positively charged, have an atom that carri
Which substance should react most readily by nucleophilic aromatic substation? 2,6-dinitrofluorobenzene
Nucleophilic aromatic substation a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring There are 6 nucleophilic substitution mechanisms encountered with aromatic systems
The highest energies are used in _____ spectroscopy of organic compounds. UV
The H-NMR signal produced by the number 2 carbon from the left of CH3CHClOCH3 should have what shape? a quartet
How many C-NMR signals is the compound para-dimethylbenzene (p-xylene) going to have? 3
Which special NMR technique allows you to associate specific H atoms with specific C atoms they are on? HETCOR
Which IR band would be within the fingerprint region of a spectrum? (all answers are in WN (1/cm)) 750
The MS of CH3C(=O)CH2CH2CH3, the main organic product after workup will be: 4-methyl-4-heptanol
Which organometallic reagents are dangerous neurotoxins? Those of Hg
What organometallic reagents have Na+ as their metal allow adding alkyne groups to carbonyl compounds? Acetylides
Grignard Reagents -One major requirement in their synthesis reaction: solvents must be ethers. -
Carbenes is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R-(C:)-R' or R=C:.
H-NMR -Also known as Proton NMR. -Large singlet with no splitting usually means isolated methyl. -Classic isopropyl signal group: a septet (area 1) and a big doublet (area 6).
C-NMR -The alkyl carbons should be identified as 45 = methine, 30 = methylene and 22 = methyl (probably) -
UV -If you have UV absorbance then you have an aromatic compound or a non aromatic compound with 2 or more conjugated double bonds.
MS -Fragment at 43 is a great match for COCH3 from a methyl ketone. -
SODAR (2C+2+N-H-X)/2 C= Carbons; N= Nitrogens; X= Halogens -Shows how many pi bonds and/or rings you have in your compound. -IF the number is greater than 4 it usually indicated an aromatic compound.
IR -Bands at 3300 indicated OH groups -Large bands at 1716 indicated C=O -
The MO structure of benzene has ___ bonding ____ anti bonding, and ____ nonbonding pi orbitals with 6pi electrons. 3,3,0
Aromatic compound aniline has the _____ group as a substituent on the basic benzene structure. -NH2
When styrene (vinylbenzene) is treated with HCl, what is the major product formed? 1-chloro-1-phenylethane
Electrophilic Aromatic Substitution (EAS) -First step involving the ring is electrons from the ring pi system attack the reagent. -Most require a cation or cationic reagent
Sulfonation Neutral species in EAS.
Meta position 1,3 position
Para Position 1,4 position
Ortho Position 1,2 position
Which of the following groups, when on a benzene ring, will both activate the ring and meta direct new EAS? None of these: -NO2, -Br, -OH
If ou wish to reduce the product of a Friedel-Crafts acylation to a hydroaron, which reagent(s) will work? Zn(Hg)+HCl
Starting with toluene, using any needed reagents, which 3 steps best make 3-Bromo-5-nitrobenzoic acid? H2SO4/NaCr2O7/HEAT; HNO3/H2SO4; BR2/FeBr3
H-NMR Cont... -Classic splitting pattern of an isolated ethyl group is a triplet (area 3) and a quartet (area 2) -
An unknown organic sub stand has a C-NMR spectrum with 5 peaks, at 14, 22, 24, 44, and 203 ppm. It is NOT: CH3CH2CH2CH2OH
To correlate the H-NMR and C-NMR spectra of a compound, so that you know which C have which H, you use: HETCOR
HETCOR, COSY, FTIR, DEPT DEPT= tells you how many H are on each C atom in a C-NMR
The majority of simple organometallic compounds are ____ and react vigorously with _____. Nucleophiles ; water
If a ketone is treated with excess Grignard or Lithium reagent, the main organic product formed by workup is: Tertiary Alcohol
An example of an activation group which is also ortho, para directing would be: -CH3
The normal reagent sequence used to place an n-butyl group on a benzene ring would be: CH3CH2CH2COCl+ AlCl3, then HCL +Zn(Hg)
If you treat 1-bromo-2-nitrobenzene with Cl2 +AlCl3, where will the Cl most likely be placed? C-4 and C-6
Which analytical method does NOT rely on the presence of energy levels of some type within a molecule? MS
The two common forms of 'hyphenated MS' combinee MS with: Chromatography
The most common alkenylbenzene compound, used in making a variety of polymers, is: Styrene
In order to be useful for substitution reactions of aromatic reigns, a reagent must be classified as a (an) Electrophile
Sulfonation of benzene is unusual in two ways; which two? The active reagent is not an ion and it is very reversible
The hydrogens on the second carbon atom of 1-chlorobutane should have a H-NMR signal which is: a triplet of triplets
Which is a limitation of 13C-NMR as it is usually perfumed? peak area doesn't correspond to the number of C
In infrared Spectroscopy the peaks that are largest are produced by: Highly polar bonds
Which of the following should have a significant UV spectrum (produce absorbances in the UV range)? 2-Phenylpropane
Organometallic reagents like Grignard and Lithium reagents are usually made by reacting: Alkyl Halides and Metals
When a Grignard reagent is reacted with formaldehyde (H2C=O) and then worked up normally, the product is: a primary alcohol
If we react excess CH3CH2MgBr wit hthe ester CH3CH2COOCH3, the major product formed after workup is (CH3CH2)3COH
The Simmons-Smith Reagent -CH2I2 + Zn(Cu) -Used to transform alkenes into cyclopropyls
When organometallic chemists study the bonding and stability of complexes, they see if the electron count on the metal is ___ , which indicates greater stability. 18
Which is correct as a description of the MO model of pi orbitals in benzene or other arenas? the pi MO's are above and below the ring
In naming the benzene ring as a substituent (C6H5-) the name it is usually given is phenyl
the usual products formed by Birch Reduction of aromatic rings with Na in NH3(l) would be called: 1,4-cyclohexadienes
Annulenes with ____ pi electrons satisfy Hückel's rule; therefore they _____ "aromatic" 10; are (4n+2), n=2
Sulfonation of an aromatic ring is most often performed using a reagent of SO3 + H2SO4
In general, if a substituent always adds electron density to an aromatic ring, that substituent will be: an activating, ortho, para-director
which species, if it is already on an aromatic ring, will tend to prevent Friedel-Crafts alkylation of the ring? -NO2
What sequence of reactions would be convert toluene into 2-bromo-4-nitrobenzioc acid? HNO3 + H2SO4, then Br2, then heat with acidic aq dichromate.
Pyridine is significantly less reactive than benzene in electrophilic aromatic substations reactions because the N in the ring reacts with Bronsted or lewis acids
In the H-NMR spectrum of 1-propanol, CH3CH2CH2OH, which of the hydrogens' signals will be further upfield: That of CH3
What shape will the H-NMR signal from the methyl group in 1-propanol be? Triplet
Relatively stable in contact with water? (CH3)4Si
Grignard reagents can be used to make alcohols; tertiary alcohols form by Grignard reaction with Ketones
Several reagents can be used to make cyclopropyl rings from alkenes, including all the following: CH2I2 + Zn(Cu), CHCl3+K(+)(-OC(CH3)3), and CH2N2
Metallocenes are transition metal organometallic compounds which use ___ ligands. cyclopentadienide
The Heck and Suzuki reaction are both useful organometallic syntheses using ___ as a key part of the process Pd
Electrophilic cont... Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons
Created by: 1315996748



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