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Nomenclature Alkanes: 1. Determine the number of carbons in the longest continuous chain. This is the parent hydrocarbon (“last name”). As this chain is six carbons long, the parent name is: hexane 2. Any groups that are not part of the chain continuous chain are substituents. Number the chain in the direction that gives the substituent the lower number. Number are used for systematic names only (never for common names). a. Name: 2 3 - dimethylhexane 3. Substituents are listed in alphabetical order. A number and word are separated by a hyphen: numbers are separated by commas. Prefixes like di, tri and tetra are ignored when alphabetizing. a. Name: 2 , 2 – dimethyl – 4 – propyloctane b. If the substituent is a branched chain then you will need to use further specialized naming. i. Name: 2,4 – dimethyl – 4 – (2 – methylpropyl)octane 4. Only if the same set of numbers is obtained in both directions does the first group cited get the lower number. a. Name: 3 – ethyl – 4 – methylhexane Regardless of the direction numbered, the substituents are on the 3 and 4 carbon of the parent chain. In this case, take a look at the substituents. In this example we have ethyl and methyl. Because ethyl comes first (alphabetically) we will preferentially give it the lower number. 5. In the case of two hydrocarbon chains with the same number of carbons, choose the parent to be one with more substituents. a. Name: 5 – butyl – 3, 4, 6 – trimethylnonane This means that the parent chain is: 6. Give the systematic name for the following: a. Name: 4 – ( 1,1 – dimethylethyl)octane b. Name: 2,2 – dimethyl – 4 – propylheptane c. Name: 3,3 – diethyl – 4 – methyl – 5 – propyloctane CH3CH2C(CH2CH3)2CH(CH3)CH(CH2CH2CH3)2 Cycloalkanes 1. In cycloalkanes with an attached alkyl substituent, the ring is the parent hydrocarbon, unless the substituent has more carbon atoms than in the ring. If there is only one substituent on a ring, do not give that substituent a number. a. Name: ethylcyclobutane 2. If the ring has two substituents they are cited in alphabetical order and the number one position is given to the substituent cited first. a. Name: 1 – ethyl – 2 – methylcyclopentane In this case the numbering is the same regardless of direction that you count the chain. So we have the flexibility to given the lower number preference to the substituents that is listed first. 3. If there is more than two substituents, the substituent given the number one is the one that results in a second substituent getting as low a number as possible. If two substituents have the same low number, the ring is numbered in the direction that gives the third substituent the lowest number possible. a. Name: 4 – ethyl – 1,2 – dimethylcyclohexane In this case we are more concerned with achieving lowest possible numbers. So the fact the ethyl is listed first does not factor into the numbering scheme. 4. Give the systematic name for the following a. Name: 2 – cyclopropylpentane H3C b. Name: CH3 1 – ethyl – 3 – (2 – methylpropyl)cyclohexane CH3 H3C CH3 Alkyl Halides 1. The common name s of the alkyl halides consist of the name of the alkyl group, followed by the name of the halogen – with the “ine” ending of the halogen name replaced with “ide”. 2. In the systematic naming, the alkyl halides are named as substituent alkanes. The prefixes for the halogens end with “o” (fluoro, chloro, bromo, iodo). 3. What is a primary, secondary and tertiary alkyl halide? 4. Give the common and systematic names for the following and indicate whether it is a primary, secondary or tertiary alkyl halide. a. Common Name: IUPAC: sec – butyl chloride 2 – chlorobutane secondary H3C CH3 Cl b. Common Name: IUPAC: cyclohexyl bromide bromocyclohexane secondary Br c. Common Name: IUPAC: isohexyl chloride 1 – chloro – 4 – methylpentane primary CH3 H3C Cl Ethers 1. The common name of an ether consists of the names of the two alkyl substituents (in alphabetical order), followed by the word “ether”. 2. In the systematic scheme an ether is named as an alkane with an RO substituents. The substituents are named by replacing the “yl” ending in the name of the alkyl substituent with “oxy”. The substituent group is the shorter of the two carbon chains. 3. Give the systematic and common names (if there is one) for the following: a. Common Name: IUPAC: ethyl methyl ether methoxyethane H3C O CH3 b. Common Name: IUPAC: butyl propyl ether 1 – propoxybutane H3C O CH3 c. Common Name: IUPAC: isopentyl isopropyl ether 3 – methyl – 1 – (1 – methylethoxy)butane CH3 H3C O CH3 CH3 d. Common Name: IUPAC: No Common Name 2 – (1 – methylethoxy)pentane CH3 H3C CH3 O CH3 Alcohols 1. The common name for an alcohol consists of the name of the alkyl group to which the OH group is attached, followed by the word “alcohol”. 2. The systematic name of an alcohol is obtained by replacing the “e” at the end of the name of the parent hydrocarbon with the suffix “ol”. 3. The parent hydrocarbon is the longest continuous chain containing the functional group. a. Name: 4. The parent hydrocarbon is numbered in the direction that gives the functional group the lowest possible number. a. Name: 5. 1 – pentanol 3 – hexanol If there is a functional group suffix and a substituent, the functional group suffix gets the lowest possible number. a. Name: 4 - methylcyclohexanol It is not necessary to include the “1” for the alcohol position. Because functional groups take priority when naming it is assumed that it is in the first position. 6. If counting in either direction gives the same number for the functional group suffix, the chain is numbered in the direction that gives a substituent the lowest possible number. a. Name: 7. 2,5 – dimethyl – 4 – heptanol If there is more than one OH functional group use prefixes to indicate the number. a. Name: 2 , 4 – hexanediol 8. What is a primary, secondary and tertiary alcohol? 9. Give the systematic name for the following and indicate whether it is primary, secondary or tertiary. a. 5 – chloro – 2 – methyl – 2 – pentanol tertiary HO CH3 H3C Cl b. 4 – bromo – 3 – ethylcyclohexanol secondary Br H3C OH c. 2, 3 – dimethyl – 1 – butanol primary CH3 H3C H3C OH Amines 1. The common name of an amine consists of the names of the alkyl groups bonded to the nitrogen, in alphabetical order, followed by “amine”. (Note that the entire name is written as one word) 2. For the systematic naming, use the suffix “amine” to denote the amine functional group. The “e” at the end of the name of the parent hydrocarbon is replaced by “amine”. A number identifies the carbon to which the nitrogen is attached. The number can appear before the name of the parent hydrocarbon (the longest carbon continuous carbon chain attached to the amine group) or before “amine”. a. Name: 3. The name of any alkyl group bonded to the nitrogen is preceded by an “N” to indicate that the group is bonded to a nitrogen rather than a carbon. a. Name: 4. 1 - hexanamine N, N – diethyl – 1 – propanamine The substituents – regardless of whether they are attached to the nitrogen or to the parent hydrocarbon – are listed in alphabetical order. Each assigned either a number or “N” denoting its location. a. Name N – (2 – methylpropyl) – 2 - butanamine 5. The chain is numbered in the direction that gives the functional group the lowest number. a. Name: N – ethyl – 3 – methylcyclopentanamine 6. What is a primary, secondary and tertiary amine? 7. Give the common (if there is one) and systematic name of the following. Also indicate whether it is a primary, secondary or tertiary amine. a. Cyclohexanamine primary NH2 b. N, N – dimethyl – 3 - pentanamine tertiary H3C H3C N CH3 CH3 c. N – ethyl – N – methylcyclohexanamine tertiary CH3 N CH3 d. 5 – methyl – 1 – hexanamine primary CH3 H3C NH2