4. Step 1: The longest carbon chain above is 5 carbons long, therefore, the base name of the molecule is pentanol. Step 2: The molecule should be numbered from right to left, placing the –OH group on C2, and the methyl groups on C3 and C4. The name is thus, 3,4-dimethyl-2-pentanol .
5. Naming cyclic alcohols The –OH group is assigned the C1 position. The second substituent then gets the lowest number. The name of the compound is 3-isopropyl-cyclopentanol
12. 1. Name the longer chain as the alkane and the shorter chain as the alkoxy group Above the longest chain is a hexane. Longest chain 2. Use IUPAC rules to finish the name. The substituent should have the smallest number possible. Thus, number from right to left. 3-methoxyhexane methoxy
16. Naming epoxides This is oxirane – the simplest epoxide These are named as substituted oxiranes 1,2-dimethyloxirane 1,1-dimethyloxirane To name an epoxide as a substituent, it is called an epoxy. This is then 1,2-epoxycyclohexane
19. Draw the product of the following two-step sequence [1] In the first step the base NaH removes the proton from the alcohol [2] In the second step of the process the alkoxide acts as a nucleophile displacing the leaving group in an S N 2 reaction
29. Think of the possibilities A 1,2-methyl shift occurs during the dehydration of this compound A 1,2-hydride shift occurs during the dehydration of this compound
30. Used curved arrows to show the methyl shift when 3,3-dimethyl-2-butanol is treated with sulfuric acid. Used curved arrows to show the hydride shift when 3-methyl-2-butanol is treated with sulfuric acid.
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33. Sometimes it is necessary to use a little more finesse in order to do a dehydration reaction with an alcohol. Reaction conditions
45. Can be used for all HI ROH RI Best for CH 3 OH and 1° and 2° alcohols PBr 3 + pyridine ROH RCBr Can be used for all HBr ROH RCBr Best for CH 3 OH and 1° and 2° alcohols SOCl 2 + pyridine ROH RCl Can be used for all HCl ROH RCl Usefullness reagent reaction