Part 7

Question 1

Br2/hv

Answer 1

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.

Question 2

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

Answer 2

c. acetaldehyde

Hydrogen is accessible at the end to oxidizing agent.

Question 3

Reagents used for oxidation of aldehydes

Answer 3

KMnO4, CrO3, Ag2O, H2O2. The product of oxidation is a CARBOXYLIC ACID.

Question 4

Carboxylic Acid + Alcohols –> ?

Answer 4

Esters.

Mixtures of COOH and -OH will condense into esters, liberating water, under acidic conditions.

Question 5

Conformational isomers

Answer 5

Compounds that differ only by rotation about one or more single bonds.

(Different positions of a compound)

Question 6

Geometric Isomers

Answer 6

Compounds that differ in the position of substituents attached to a double bond. (e.g. cis/trans and Z/E)

Question 7

Acetone

Answer 7

(CH3)2C(=O)

Question 8

Heats of hydrogenation

Answer 8

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.

Question 9

Which of the following could be the formula for an ester?

a. C6H12O
b. C7H12O2
c. C7H14O
d. C7H16O2
e. C7H16O

Answer 9

b. C7H12O2

Question 10

William Ether Synthesis

Answer 10

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.

Question 11

What is the product of the following reaction:

CH3Cl + CH3O-Na+ –> ?

Answer 11

CH3OCH3

William ether synthesis reaction.

Question 12

With molecular formular CH4, how many structural isomers can be formed? C2H6? C3H8? C4H10? C5H12? C6H14? C7H16? C8H18? C9H20? C10H22?

Answer 12

CH4 = 1
C2H6 = 1
C3H8 = 1
C4H10 = 2
C5H12 = 3
C6H14 = 5
C7H16 = 9
C8H18 = 18
C9H20 = 35
C10H22 = 75

Question 13

Aromatic (with C2H5) attached + KMnO4 –> + SOCl2 –> + HCN –> + H2O –> ?

what is final product of these reactions?

Answer 13

aromatic + C(=O)COOH

Question 14

Thionyl Chloride

Answer 14

SOCl2

Used to convert carboxylic acids to acyl chlorides.

Also alcohols to corresponding alkyl chlorides.

Question 15

acetal

Answer 15

Molecule with two single bonded oxygens attached to the same carbon atom.

Question 16

Ketal

Answer 16

Functional group or molecule containing the functional group of a carbon bonded to two -OR groups.

Question 17

Purine

Answer 17

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)

Question 18

Pyrmidine

Answer 18

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.

Question 19

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

Answer 19

c. HCHO

converts ketones and esters to alcohols.

Question 20

D2O

Answer 20

Heavy water. or H2O.

Question 21

CH3MgBr + D2O –> ?

Answer 21

DCH3

Question 22

Ch3MgBr + CO2 –> ?

Answer 22

CH3COO-

Question 23

The base-catalyzed condensation products of two acetaldehyde molecules is…

Answer 23

a beta-hydroxylaldehyde