10. Addition Reactions

Which compound is formed as the major oxidation product when cyclohexene is treated with cold, dilute ${\mathrm{KMnO}}_4$ in water?

Alkenes undergo an addition reaction with borane in tetrahydrofuran (THF). For the reaction below: $R-C=CH\mathrm{R\text{'}}$ + $B_{2}H6$ (in THF) → product. What is the major organic product of this hydroboration-oxidation sequence after subsequent treatment with hydrogen peroxide and sodium hydroxide?

When $H_{\mathrm{Br}}$ is added in a 1:1 ratio to an unsymmetrical diene such as 1,3-butadiene, which of the following best describes the major products formed from mono addition?

Which of the following represents the structure of the product formed when $C_2{H}_4$ reacts with water in the presence of an acid catalyst?

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(a)

Which compound is formed when 1-butene reacts with bromine (${\mathrm{Br}}_2$) in an inert solvent?

Consider the addition reaction shown: ${\mathrm{CH}}_2={\mathrm{CH}}_2$ reacts with $\mathrm{HBr}$. Which major product is formed according to Markovnikov's rule?

When $2-\mathrm{butene}$ reacts with bromine (${\mathrm{Br}}_2$) in carbon tetrachloride (${\mathrm{CCl}}_4$), predict the two major organic products of the reaction.

In the electrophilic addition of $H_{2}O$ to propene, what is the major organic product formed?

Which of the following is the major neutral organic product formed when $\mathrm{cycloheptene}$ reacts with $H{2}_{}O$ in the presence of $H{2}_{}\mathrm{SO}{4}_{}$?

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(a) meso-2,7-dimethyloctane-4,5-diol, (CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂.

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.

a. ethyl bromide

b. tert-butyl bromide

c. formaldehyde

Show how you would accomplish the following synthetic conversions.

c. 1-methylcyclopentanol → 2-chloro-1-methylcyclopentanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.