You are working in a pharmaceutical research lab and need to retrieve reagents from storage. The compounds are arranged alphabetically, so you need to determine the names from the structural formulas given in the synthetic procedures you are testing. Name the compounds

(a) CH₃CH(CH₃)CH(OH)CH₃;

(b) CH₃CHClCH₂COCH₃; and

(c) (CH₃CH₂)₂NCH₂CH₂CH₃.

PLAN Follow the procedures in Toolbox 11D.1.

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Toolbox 11D.1 HOW TO NAME SIMPLE COMPOUNDS WITH FUNCTIONAL GROUPS CONCEPTUAL BASIS In general, the names of compounds containing functional groups follow the same conventions and numbering system as those used in the names of hydrocarbons (Toolbox 11A.1), with the ending of the name changed to indicate the functional group. The aim here, as there, is to be succinct but unambiguous. PROCEDURE The functional group has priority in numbering over hydrocar- bon side chains. Alcohols To form the systematic name, identify the parent hydrocarbon and replace the ending -e by -ol. The location of the hydroxyl group is denoted by numbering the C atoms of the backbone, starting at the end of the chain that results in the lowest number for the -OH group location. When -OH is named as a sub- stituent, it is called hydroxy. For example, CH,CH(OH) CHCHCH, is 2-pentanol or 2-hydroxypentane. Aldehydes and ketones For aldehydes, identify the parent hydrocarbon: include the C of -CHO in the count of carbon atoms. Then change the final -e of the hydrocarbon name to -al. The C in the -CHO group is always carbon 1, at the end of a carbon chain, and is not explic- itly numbered. For ketones, change the -e of the parent hydrocarbon to one and number the chain in the order that gives the carbonyl group the lower number. Thus, CH3CHCHCOCH, is 2-pentanone. Carboxylic acids Change the -e of the parent hydrocarbon to-oic acid. To identify the parent acid, include the C atom of the -COOH group when counting carbon atoms. Thus, CHCHCHCOOH is butanoic acid. Esters Change the -anol of the alcohol to -yl and the -oic acid of the parent acid to -oate. Thus, CH,COOCH, (from methanol and ethanoic acid) is methyl ethanoate. Amines Amines are named systematically by specifying the groups attached to the nitrogen atom in alphabetical order (disregard- ing prefixes), followed by the suffix -amine. Amines with two amino groups are called diamines. The-NH group is called amino- when it is a substituent. Thus, (CHCH)NCH, is dieth- ylmethylamine and CHCH(NH)CH, is 2-aminopropane. Halides Name the halogen atom as a substituent by changing the -ine part of its name to -o, as in 2-chlorobutane, CHCHCICHCH. These rules are illustrated in Example 11D.1.