Part 7
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Br2/hv
Free radical halogenation. Will add to most substituted carbon. Bromine is picky, but chlorine will more rapid and depends not only on the stability of intermediate, but on the number of hydrogens present.
Which compound will undergo an oxidation reaction without the cleavage of any covalent bond between two carbons? a. t-butyl alcohol b. ethyl methyl ketone c. acetaldehyde d. acetate e. all of the above
c. acetaldehyde Hydrogen is accessible at the end to oxidizing agent.
Reagents used for oxidation of aldehydes
KMnO4, CrO3, Ag2O, H2O2. The product of oxidation is a CARBOXYLIC ACID.
Carboxylic Acid + Alcohols –> ?
Esters. Mixtures of COOH and -OH will condense into esters, liberating water, under acidic conditions.
Conformational isomers
Compounds that differ only by rotation about one or more single bonds. (Different positions of a compound)
Geometric Isomers
Compounds that differ in the position of substituents attached to a double bond. (e.g. cis/trans and Z/E)
Acetone
(CH3)2C(=O)
Heats of hydrogenation
Heats of hydrogenation can be used to measure the relative stability of isomeric alkenes. Heats of hydrogenation correlate with structure just like heats of combustion do. The greater the heat of hydrogenation, the less stable the alkene.
Which of the following could be the formula for an ester? a. C6H12O b. C7H12O2 c. C7H14O d. C7H16O2 e. C7H16O
b. C7H12O2
William Ether Synthesis
Produces ethers from the reaction of metal alkoxides with primary alkyl halides or tosylates. Alkoxides behave as nucleophiles, displacing halide or tosylate via an SN2 reaction, producing an ether.
What is the product of the following reaction: CH3Cl + CH3O-Na+ –> ?
CH3OCH3 William ether synthesis reaction.
With molecular formular CH4, how many structural isomers can be formed? C2H6? C3H8? C4H10? C5H12? C6H14? C7H16? C8H18? C9H20? C10H22?
CH4 = 1 C2H6 = 1 C3H8 = 1 C4H10 = 2 C5H12 = 3 C6H14 = 5 C7H16 = 9 C8H18 = 18 C9H20 = 35 C10H22 = 75
Aromatic (with C2H5) attached + KMnO4 –> + SOCl2 –> + HCN –> + H2O –> ? what is final product of these reactions?
aromatic + C(=O)COOH
Thionyl Chloride
SOCl2 Used to convert carboxylic acids to acyl chlorides. Also alcohols to corresponding alkyl chlorides.
acetal
Molecule with two single bonded oxygens attached to the same carbon atom.
Ketal
Functional group or molecule containing the functional group of a carbon bonded to two -OR groups.
Purine
Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. (4 nitrogens: 2 in hexane ring, 2 in pentane. They are attached)
Pyrmidine
Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring.
To prepare a primary alcohol with a grignard reagent, the grignard reagent must react only with a. CH3COCH3 b. CH2CHO C. HCHO d. HCOOH e. CO2
c. HCHO converts ketones and esters to alcohols.
D2O
Heavy water. or H2O.
CH3MgBr + D2O –> ?
DCH3
Ch3MgBr + CO2 –> ?
CH3COO-
The base-catalyzed condensation products of two acetaldehyde molecules is…
a beta-hydroxylaldehyde