Answer to Question #94135 in Organic Chemistry for Valentine Michael

Question

1. Consider compound A= 2 chloro 2 methyl butane, B= 2 chloro butane, C= chloro propane.
(i). Which of the compound will readily undergo dehydrochlorination
(ii). What informs your answer?

2. Give structures of the compounds that produces the following pairs of compounds upon ozonolysis
(i). 4-hydroxy 3-phenyl pentan-2-one and phenyl butanone
(ii). 2, 5 dimethyl hexane 1, 6 dial
(iii). 3-oxo 2 phenyl butanoic acid and 4-bromo, 2, 2 dihydroxyphenylalanine 4-butanal
(iv). Cyclo pentanoic acid and 3-hydroxy 3-phenyl butanoic acid

3. State the products of the following reactions
(i). Hydrobromination of 2, 4, dimethyl pent-2-ene
(ii). Hydrolysis of 2 methyl pent-2-ene in the presence of hydrogen peroxide
(iii). Ozonolysis of 2-methyl hex-2-ene in the presence of Zn and CH3COOH

Answer 1

1.The answer is compound A. If the mechanism of elimination is E1 then the reactivity of dehydrohalogenation is dependent on stability of carbocation. The more stable the carbocation the more readily it undergoes the reaction. The compound A will produce tertiary carbocation, the most stable one.

2.See the structures attached in the picture

i) (E)-4-methyl-3,8-diphenyloct-4-en-2-ol

ii) 3,6-dimethylcyclohex-1-ene

iii) (E)-7-bromo-5,5-dihydroxy-3-methyl-2-phenylhept-3-enoic acid

iv) (E)-5-cyclopentyl-2-phenylpent-4-en-2-ol

3. i) 2-bromo-2,4-dimethylpentane

ii) 2-hydroxy-2-methylpentane

iii) isopropyl alcohol and 1-butanol