Answer to Question #94009 in Organic Chemistry for Isaac Samuel

Question

Q1_Consider a compound A-2chloro-2methyl butane,B-2chlorobutane,C-chloro-propane,1:which of the compound will readily undergo dehydrochlorination.2:what informs your answer.
Give structures of the compounds that produces the following pairs of compounds upon ozonolysis:
i-4-hydro-3phenyl-pentan-2-one and phenyl butanone.ii-2,5dimethylhexane,1,6,diol.
iii-3-oxo-2phenylbutanoic acid and 4-bromo-2,2,dihydroxy-4-butanal
iv-cyclopentanoic acid and 3-hydroxy-3phenylbutanoic acid.
3-state the products of the following reactions: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-2ene in the presence of zinc 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