1. Winning Fifty Points Revision 430 Chem.

2. A) 1,1,1,6-tetramethyl-2,4-heptanediol B) 2,2,7-trimethyl-3,5-octanediol C) 2,2,6,6-tetramethyl-3,5-heptanediol D) 2,7,7-trimethyl-4,6-octanediol What is the IUPAC name for (CH 3 ) 3 CCH(OH)CH 2 CH(OH)CH 2 CH(CH 3 ) 2 ? B) 2,2,7-trimethyl-3,5-octanediol

3. A) C 2 H 5 OH B) C 2 H 5 O (-) K (+) C) NaCN D) (CH 3 ) 3 N Which of the following reagents would you expect to react with bromocyclopentane by an S N 2 mechanism ? C) NaCN

4. A) 2-methyl-2-pentene B) 4-methyl-1-pentene C) 2,3-dimethyl-2-butene D) 3-methyl-1-pentene Compound X (C 6 H 12 ) reacts with HI. The product of this reaction, when treated with KOH in ethanol, gives Y ( an isomer of X ). Ozonolysis of X (H 2 O 2 workup) produces two compounds: a two carbon Aldehyde, and a four carbon ketone. What is X? A) 2-methyl-2-pentene

5. A) 1-methylcyclohexanol B) 3,3-dimethylcyclopentanol C) 3-methyl-1-hexanol D) 3-ethyl-3-hexanol Which one of the following alcohols will be oxidized by (CrO 3 in 50% sulphuric acid) to a ketone having the same number of carbon atoms ? B) 3,3-dimethylcyclopentanol

6. A) H 3 O + & heat B) (i) HgSO 4 in H 2 O (ii) NaBH 4 C) (i) B 2 H 6 in ether (ii) H 2 O 2 and base D) (i) HOBr (ii) Mg in ether Which reagent(s) would best accomplish the following transformation A) H 3 O + & heat

7. A) HCl & ZnCl 2 B) PCl 3 C) SOCl 2 D) KCl (5 molar solution) Which of the following reagents would not effect the following transformation? D) KCl (5 molar solution)

8. A) cis-4-methylcyclohexyl bromide B) trans-3-methylcyclohexyl bromide C) cis-2-methylcyclohexyl bromide D) trans-2-methylcyclohexyl bromide A C 7 H 13 Br compound reacts with KOH in ethanol to form 3- methylcyclohexene as the major product. What is a likely structure for the starting alkyl bromide? B) trans-3-methylcyclohexyl bromide

9. A) the two methods give the same product B) (i) gives a chiral isomer, (ii) gives an achiral isomer C) (i) gives an achiral isomer, (ii) gives a chiral isomer D) two different isomers are formed, but both are chiral Synthesis of hexane-3,4-diol from trans-3-hexene may be accomplished in two ways: (i) OsO 4 hydroxylation & (ii) C 6 H 5 CO 3 H epoxidation followed by NaOH opening of the epoxide ring. Which of the following statements about the products from these reactions is correct? C) (i) gives an achiral isomer, (ii) gives a chiral isomer

10. A) (i) Mg in ether;.(ii) ethylene oxide (C 2 H 4 O); (iii) HI & heat B) (i) NaC≡CH in ether;.(ii) H 2 + Lindlar catalyst; (iii) HI C) (i) KOH in alcohol;. (ii) C 6 H 5 CO 3 H in CH 2 Cl 2 ; (iii) NaC≡CH in ether ; (iv) 2 H 2 + Pt catalyst D) (i) NaC≡CH in ether;.(ii) H 3 O + + HgSO 4 ; (iii) HI & heat Which of the following reaction sequences would best serve to convert 2-methyl-1- bromopropane to 4-methyl-1-iodopentane? A) (i) Mg in ether;.(ii) ethylene oxide (C 2 H 4 O); (iii) HI & heat

11. A) H 3 PO 4 B) POCl 3 in CH 2 Cl 2 C) Jones' reagent (H 2 CrO 4 )or KMnO 4 / H + D) OsO 4 Which of the following reagents would be best for oxidizing a 1º-alcohol to an aldehyde? C) Jones' reagent (H 2 CrO 4 ) or KMnO 4 / H +