2. Rank the following molecules based upon reaction with H:O/HSO. (Fastest reacting alkene first). d. iii >i> ii e. ii ili>i 3. Addition of hydrogen chloride to the following molecule would produce: CI Cl Cl CI HCI CI CI Cl IV a. I and II b. II and III c. I and IV d. III and IVe. V 4. Determine the starting material for the following reaction. 1, NaOEt, EtOH, heat 2. Hg(OAc)h. THF. heat 3. NaBHa Br 5. Identify the alkene with the largest molar heat of hydrogenation (most exothermic). Solution 2) option B is correct Explanation: Reaction of alkene with H2O, H2SO4 involves formation of carbocation as an intermediate. Benzyl cation is more stable so it reacts fastest then tertiary carbocation is more stable than secondary so structure III is faster than II. 3) option A is correct Explanation: Addition of HCl to alkene produces carbocation as an intermediate. Now, the nucleophile attacks the carbocation and produces racemic mixture of products. 4) option B is the starting material Explanation: NaOEt is a base which gives elimination reaction and produces alkene as product. Oxymercuration-demercuration of alkene with Hg(OAc)2, THF and NaBH4 produces more substituted alcohol which on further cyclization produces the required product. .

1. 2. Rank the following molecules based upon reaction with H:O/HSO. (Fastest reacting alkene
first). d. iii >i> ii e. ii ili>i 3. Addition of hydrogen chloride to the following molecule would
produce: CI Cl Cl CI HCI CI CI Cl IV a. I and II b. II and III c. I and IV d. III and IVe. V 4.
Determine the starting material for the following reaction. 1, NaOEt, EtOH, heat 2. Hg(OAc)h.
THF. heat 3. NaBHa Br 5. Identify the alkene with the largest molar heat of hydrogenation (most
exothermic).
Solution
2) option B is correct
Explanation: Reaction of alkene with H2O, H2SO4 involves formation of carbocation as an
intermediate. Benzyl cation is more stable so it reacts fastest then tertiary carbocation is more
stable than secondary so structure III is faster than II.
3) option A is correct
Explanation: Addition of HCl to alkene produces carbocation as an intermediate. Now, the
nucleophile attacks the carbocation and produces racemic mixture of products.
4) option B is the starting material
Explanation: NaOEt is a base which gives elimination reaction and produces alkene as product.
Oxymercuration-demercuration of alkene with Hg(OAc)2, THF and NaBH4 produces more
substituted alcohol which on further cyclization produces the required product.