23) Which reaction will yield the following alkene as only elimination product? NaOEt A) Br E-3. Br NaOCH, B) KOIBU Br KHSO,JAT D) 24) What is the product of the following transformation? A9OH Br A) B) OH C) D) он ÕH 25) Rank the following alkenes according to their heat of combustion from the LOWEST to the HIGHEST. II II IV A) II < IV < I< Il B) III < I< IV < || C)I< Il < IV < II D) II < IV < I| < I

Which of the following reaction sequences would you use to convert 1- methylcyclohexene to the product 2 ? OH 2 O A) Oxymercuration-Demercuration O B) Hydroboration-Oxidation O C) Os04 / Pyridinc- NalHSO3 O D CH3CO3H- H30+

4) Show how you could make the following from 1,2-dimethylcyclohexene. OH хасах d) OH a) b) ОН ОН c) Br Br

10) Which of the following additions to alkenes occur(s) specifically in an syn fashion? A) dihydroxylation using OsO4, H2O2 B) addition of H2 C) hydroboration D) addition of HCl E) A, B, and C

3. Which of the following is the major product of the reaction? A) Br Br B) Br HBr -15°C + Br D) Br

For each reaction below suggest structures for alkenes that give the indicated reaction products. There may be more than one answer in some cases

Draw the alkene starting material of the reaction shown below. Ignore inorganic byproducts. I Drawing KMnO4 KOH HO E OHH I I

ОН CH3CH2CH2CH2ČHCH3 Can this alcohol be synthesized selectively by hydroboration-oxidation of an alkene? • If yes, draw the structure of the alkene. • If no, draw the structure given above. • You do not have to explicitly draw H atoms. opy aste ChemDoodle

What is the major product formed in the following reaction? Ο 1) NaOCH3 CH3OH Major Product 2) H3O+ LOCH3 LOH H3CO. H3CO, H3CO OH a) b) c) HO HO _ OCH 3 OCH3 d) e) C 635 x 481

two equivalents of HBr! a) ) Draw the organic product when each alkyne is treated with CH₂CH₂CH₂CH₂-C=CH b) H3C-C=C-CH(CH3)2 1 JL