Predict the products you would get when the following alkenes undergo (i) hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂ or (ii) oxymercuration–reduction [1. Hg(OAc)₂, H₂O 2. NaBH₄].

(a)

Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)₂ , H₂O 2. NaBH₄ ].

(b)

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(c)

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(d)

Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(e) 

Unlike hydroboration–oxidation, the addition of H₂O catalyzed by H₃O⁺ is not stereospecific. Thinking carefully about the mechanism of the reaction, give two reasons why.

The first step of oxymercuration–reduction is stereospecific, and yet this fact wasn't emphasized in that discussion. Show the stereospecificity of the first step for the following alkene and then explain why the stereospecificity becomes unimportant after the second step.

Calculate the index of hydrogen deficiency for the following molecular formulas and structures.

(a)

Calculate the index of hydrogen deficiency for the following molecular formulas and structures.

(b)

Calculate the index of hydrogen deficiency for the following molecular formulas and structures.

(c)

Calculate the index of hydrogen deficiency for the following molecular formulas and structures.

(f) C₆H₈O₂

Using IUPAC rules, name the following molecules.

(a)

Using IUPAC rules, name the following molecules.

(c)

Using IUPAC rules, name the following molecules.

(d)

Using IUPAC rules, name the following molecules.

(e)

Using IUPAC rules, name the following molecules.

(g)

Given the name, draw the structure of the following compounds.

(b) (4Z,8R)-8-bromo-5-methylnon-4-ene

Given the name, draw the structure of the following compounds.

(c) (3S,6Z)-8-ethyl-3-iododeca-1,5-diene

Given the name, draw the structure of the following compounds.

(e) (3R,5S)-5-chloro-3-isopropylcycloheptene

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr;

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl;

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr; (ii) HCl; (iii) HBr, H₂O₂ (iv) H₂SO₄, H₂O (v) 1. Hg(OAc)_2, H₂O 2. NaBH₄ ; (vi) 1. BH₃ 2. H₂O₂, NaOH

(d)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(g)