Chapter 21: Phenomena Phenomena: Below are the names and pictures of - PowerPoint PPT Presentation

Chapter 21: Phenomena Phenomena: Below are the names and pictures of several organic compounds. Can you determine the naming conventions of these compounds? What are the b) CH 3 a) c) H 2 C CH 2 CH 2 CH 3 names of the H 3 CH 3 C CH ethane following H 2 C CH 2 H 3 CH 2 CH 2 C structures and heptane d) H 3 CH 2 CH 2 CH 3 C CH 2 CH 2 why? methylcyclopentane butane e) g) CH 2 CH 2 f) CH 3 H 2 C CH 2 H 3 C CH 2 H 2 C CH 2 CHCH 2 CH 3 H 3 CH C H 2 C CH 2 CH 2 CH 2 cyclobutane CH 3 cyclopentane H 3 CH C 2,3-dimethylpentane CH 3 j) CH 3 h) H 3 C i) CH 3 H 3 CH C CH 3 CH 2 CH methylpropane CH 2 CH 3 H 3 CH C H 2 C CH 2 methylbutane CH 2 H 2 C CH 3 H 2 C CH 2 methylcyclopropane m) CH 2 k) l) CH H 3 CH 2 CH 2 CH 2 CH 3 C H 3 CH 2 CH 2 CH 2 CH 2 CH 3 C H 3 C CH 2 CH CH 2 CH 2 CH 3 pentane H 2 CH 2 CH 3 C 3-ethylhexane hexane Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es

Chapter 21: Organic and Biochemical Big Idea: The large number of Molecules hydrocarbons arise from the ability of • Simple Organic carbon atoms to form Molecules long chains and rings with one another. The • Isomers properties of • Functional Groups hydrocarbons are • Organic Reactions dominated by the • Polymers functional groups • Biochemistry present. Functional groups properties are independent of their bonding environment. 2

Simple Organic Molecules Structural Representations Lewis Structure H H H H H H H C C C C C C H H H H H H H Chemical Formula CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Line notation Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 3

Simple Organic Molecules Structural Representations Lewis Structure Line Notation O Not ote: When other groups of  Chemical Formula hydrocarbons are coming off of a longer chain of carbons CH 2 CHC(CH 3 ) 2 CH 2 OCH 3 they are put in parentheses in the chemical formula. Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 4

Simple Organic Molecules Short Space Long Chemical Chemical Name Filling Short Hand Formula Formula Model H CH 4 Methane CH 4 C H H H C 2 H 6 Ethane CH 3 CH 3 C 3 H 8 Propane CH 3 CH 2 CH 3 C 4 H 10 Butane CH 3 CH 2 CH 2 CH 3 C 5 H 12 Pentane CH 3 CH 2 CH 2 CH 2 CH 3 Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 5

Simple Organic Molecules Short Space Chemical Long Chemical Formula Name Filling Short Hand Formula Model C 6 H 14 Hexane CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 C 7 H 16 Heptane C 8 H 18 Octane CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 C 9 H 20 Nonane CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 C 10 H 22 Decane CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 6

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) Example: The longest continuous chain of carbon  1. atoms determines the root name for the hydrocarbon. Note the longest chain might not be in a straight line. Example: The longest chain will be named by  2. taking the core name and adding -ane. # of Carbons Core Name # of Carbons CoreName root name: hexane 1 meth- 6 hex- 2 eth- 7 hept- 3 prop- 8 oct- 4 but- 9 nan- 5 pent- 10 dec- Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 7

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) When alkane groups 3. Example:  appears as a CH 3 CH 2 - ethyl substituent (bonded to a larger alkane), they are named by taking the core name and adding – yl. When halogens are 4. Halogen Name present as substituents F fluoro they are named using Cl chloro the following: Br bromo I iodo Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 8

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) When multiple of the same Example: 5.  trimethyl substituents are present the appropriate prefix is added to the name of the substituent. # of the same Name substituents 2 di- 3 tri- 4 tetra- Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 9

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) Number the carbons in Example: 6.  the chain so that the Correct Incorrect lowest number is given 3 2 1 4 2 4 3 1 to the substituent. If both directions give 7. Example:  the same lowest number for the 1 st Correct Incorrect substituent then use the 1 5 3 3 5 1 numbering which gives 2 4 4 2 the lowest number for 2,2,4 2,4,4 the 2 nd substituent. Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 10

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) If two numbering schemes 8. have the same lowest Example:  numbering scheme, give the Correct Incorrect lowest number to the 3 4 substituent that appears first in 5 1 2 6 6 2 1 5 4 3 the name. Cl Cl In front of each substituent, list 9. the carbon number in which the substituent is bonds to in the Example:  alkane. If there are multiple of 2,2,4-trimethyl one type of substituent, multiple numbers will need to be used. 4 Separate multiple numbers with 2 1 3 5 comas. Separate the number 6 from the name with a hyphen. Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 11

Simple Organic Molecules  Rules for Naming Branching Alkanes (C n H 2n+2 ) 10. Substituents are listed in alphabetic order with respect to their root name (methyl, ethyl etc.). If multiple substituents are present, they are separated from each other with a hyphen. The substituent that is closest to the root name is combined with the root name. Example:  4-ethyl-2,3-dimethyloctane Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 12

Simple Organic Molecules isopropyl CH 3 CHCH 3 R H isobutyl ― CH 2 ―C―CH 3 R CH 3 sec-butyl CH 3 CHCH 2 CH 3 R CH 3 tert -butyl ―C―CH 3 R CH 3 Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 13

Simple Organic Molecules Student Question Which of the following has the lowest boiling point? a) Butane b) Ethane c) Propane d) Methane Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 14

Simple Organic Molecules  Rules for Naming Alkene and Alkynes If a double bond is present, 1. Example:  the root hydrocarbon is the pentene longest chain that contains the double bond. The root hydrocarbon will be named by adding – ene to the core. If a triple bond is present, the 2. root hydrocarbon is the Example:  longest chain that contains butyne the triple bond. The root hydrocarbon will be named by adding – yne to the core. Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 15

Simple Organic Molecules  Rules for Naming Alkene and Alkynes If multiple double and 3. Example: heptadiene triple bonds are present  the following notation is placed in front of the – ene # of bonds Name or – yne suffix which 2 di- identifies the number of 3 tri- bonds in addition an “a” is 4 tetra- added to the root name. Example: The root chain will be  4. numbered so that multiple Correct bonds get the lowest 2 4 6 8 possible number. This takes 1 7 3 5 Incorrect precedence over giving branching hydrocarbons or 7 5 3 1 halogens. 8 2 6 4 Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 16

Simple Organic Molecules  Rules for Naming Alkene and Alkynes Example:  Bonds are numbered in the 5. C Numbers Bond Numbers same order as the carbons. 2 4 6 8 7 3 5 1 4 6 2 1 7 3 5 The bond number is placed in 6. Example:  front of the root name. If there root name: 3-octene are multiple double or triple bonds, multiple numbers will need to be used. Separate multiple numbers with comas. Separate the number from the name with a hyphen. Example: Usethe rules for naming  7. 7-methyl-3-octene alkanes to name the rest of the substituents. Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 17

Simple Organic Molecules  Rules for Naming Cyclic Hydrocarbons Use a ring for the root name if the ring has more 1. carbons than any of the other chains. The root name is formed by adding the prefix cyclo- to 2. the core name (indicating the number of carbons). If only single bonds exist in the ring, the suffix – ane is 3. added to the core name. If double bonds exist in the ring, the suffix – ene is added 4. to the core name. If multiple double bonds exist, include di-, -tri-, etc. Number the cyclic hydrocarbon so that double bonds 5. get preference over halogen or hydrocarbon chains Examples: 3  2 2 4 3 1 1 5 4 Chapt pter er 21: : Organi nic c and Bioch chemi emical cal Molecul ecules es 18