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1 Monday, September 10th Review Chapter 11 iclicker Quiz #1 Chapter 12 Chapter 13(maybe) Group assignment Keep checking the class webpage at Go to the course tab then CHEM107 Lecture notes Naming chart Coming soon-quiz #1 and answer key Frequency: BB

2 Organic Compounds An organic compound typically contains carbon and hydrogen atoms, and may also contain other atoms, such as, O, S, N, P, or a halogen (F, Cl, Br and I). Propane, C 3 H 8

3 Properties of Organic Compounds Many organic compounds are nonpolar and have weak attractions between molecules. have low melting and boiling points. are not soluble in water. are less dense than water. are highly flammable. Oil (organic) and water (inorganic)

4 Alkanes Contain only C-C and C-H bonds Saturated hydrocarbons Methane CH 4 Ethane C 2 H 6 Propane C 3 H 8 Butane C 4 H 10 Pentane C 5 H 12 Hexane C 6 H 14 Heptane C 7 H 16 Octane C 8 H 18 Nonane C 9 H 20 Decane C 10 H 22 CH 4 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2

5 Naming Alkanes with Substituents

6 What Is in a Name? The structural formula is drawn from the IUPAC name. 2,4-dimethylhexane 2,4 dimethyl hexane Location of Two - groups 6-carbon main chain branches on attached with single C C carbon main chain atoms

7 Isomers of Pentane (C 5 H 12 ) Isomers of pentane have the same molecular formula. have different structural arrangements. consist of a straight chain and two branched chains.

8 Structures of Cycloalkanes Cycloalkanes are named by using the prefix cyclo- before the name of the alkane chain.

9 iclicker Quiz #1 Take out your iclicker! If you do not have an iclicker yet, get a piece of paper. Frequency: BB

10 Back to Chapter 11.4

11 Combustion of Alkanes Alkanes contain single C C bonds which are difficult to break. are the least reactive group of organic compounds. burn readily in the presence of oxygen. undergo combustion to produce carbon dioxide, water, and energy.

12 Combustion of Alkanes We use methane gas to cook food and heat homes. Propane gas is used in portable heaters and gas barbecues. Our cells get energy from the combustion of glucose.

13 Balancing a Combustion Write the equation: Equation Balance C: Balance H: Balance O with O 2 :

14 Crude Oil Hydrocarbons in crude oil are separated by their different boiling points in a process called fractional distillation which removes groups of hydrocarbons by continually heating the mixture to higher temperatures.

15 Crude Oil

16 Elements in Organic Compounds In organic molecules, carbon atoms can form bonds with atoms of O, S, N, P, or halogens, F, Cl, and Br Pearson Education, Inc. Chapter 11, Section 4 16

17 Functional Groups Functional groups are a characteristic feature of organic molecules that behave in a predictable way. are composed of an atom or a group of atoms. are groups that replace a H in the corresponding alkane. provide a way to classify families of organic compounds. 17

18 Some Functional Groups 18

19 Alkenes and Alkynes Alkenes contain a double bond between adjacent carbon atoms. C C Alkynes contain a triple bond. C C Aromatic compounds contain a benzene ring Pearson Education, Inc. Chapter 11, Section 5 19

20 Alcohols, Thiols, and Ethers An alcohol contains the hydroxyl ( OH) functional group. H 3 C CH 2 OH Thiols contain a thiol ( SH) functional group. H 3 C CH 2 SH In an ether, an oxygen atom is bonded to two carbon atoms ( C O C ). Thiol H 3 C O 20

21 Aldehydes and Ketones An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom, attached to at least one hydrogen atom. H 3 C O C H In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms. O C H 3 C 21

22 Carboxylic Acids and Esters Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. An ester contains the carboxyl group between carbon atoms. O H 3 C O C OH H 3 C C O 22

23 Amines and Amides In an amine, the functional group is a nitrogen atom. H 3 C N H H 3 C N H H 3 C N H In an amide, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group. O H 3 C C NH Pearson Education, Inc. Chapter 11, Section 4 23

24 iclicker Questions 1. Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. a) anime b) alcohol c) ester d) carboxylic acid e) ether HO CH 2 CH 2 24

25 iclicker Questions 2. Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. a) anime b) alcohol c) ester d) carboxylic acid e) ether H 3 C O CH 2

26 iclicker Questions 3. Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. a) anime b) alcohol c) ester d) carboxylic acid e) ether H 3 C CH 2 NH 2

27 iclicker Questions 4. Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. O a) anime b) alcohol c) ester d) carboxylic acid e) ether H 3 C C OH

28 iclicker Questions 5. Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. O a) anime b) alcohol c) ester d) carboxylic acid e) ether H 3 C C O

29 Solutions Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine. A. B. C. D. E. HO CH 2 CH 2 H 3 C O CH 2 H 3 C CH 2 NH 2 O H 3 C C OH O H 3 C C O alcohol ether amine carboxylic acid ester 29

30 Unsaturated Hydrocarbons Unsaturated hydrocarbons do not contain the maximum number of hydrogen atoms that could be attached to each carbon atom. are alkenes when they contain double C=C bonds. are alkynes when they contain triple C C bonds. nskis/courses/chem107/tabi d/12265/default.aspx

31 iclicker Questions 1. Identify the following compound as an alkane, alkene, or alkyne. a) alkane b) alkene c) alkyne

32 iclicker Questions 2. Identify the following compound as an alkane, alkene, or alkyne. a) alkane b) alkene c) alkyne

33 iclicker Questions 3. Identify the following compound as an alkane, alkene, or alkyne. a) alkane b) alkene c) alkyne

34 iclicker Questions 4. Identify each of the following compounds as an alkane, alkene, or alkyne. a) alkane b) alkene c) alkyne

35 Solution Identify each of the following compounds as an alkane, alkene, or alkyne. A. alkyne B. alkene C. alkene D. alkane

36 Naming Alkenes and Alkynes The names of alkenes and alkynes use the corresponding alkane name for the longest carbon chain. change the ending from ane to ene for an alkene, ane to yne for an alkyne. Chapter 11, Section Pearson Education, Inc. 36

37 Guide to Naming Alkenes and Alkynes

38 Naming Alkenes and Alkynes Write the IUPAC name for the following. A. B. Step 1 Name the longest carbon chain that contains the double or triple bond. Analyze the Problem. Functional Group Class IUPAC Naming A. Double bond Alkene Replace ane of alkane with ene B. Triple bond Alkyne Replace ane of alkane with yne IUPAC Name Alkene Alkyne

39 Naming Alkenes and Alkynes Write the IUPAC name for the following. A. B. Step 1 Name the longest carbon chain that contains the double or triple bond. A. B. butene heptyne

40 Naming Alkenes and Alkynes Write the IUPAC name for the following. A. B. Step 2 Number the carbon chain from the end nearer the double or triple bond. A B butene 2 heptyne

41 Naming Alkenes and Alkynes Write the IUPAC name for A. B. Step 3 Give the location and name of each substituent (alphabetical order) as a prefix to the alkene or alkyne name. A. B butene methyl 2 heptyne

42 Naming Cycloalkenes When naming a cycloalkene, if there are no substituents, the double bond does not need a number. if there is a substituent, the carbons in the double bond are numbered as 1 and 2, and the ring is numbered from carbon 2 in the direction that will give the lower number to the substituent. cyclopentene 3-methylcyclohexene 3 1 2

43 Learning Check Write the IUPAC name for the following compounds. CH A. 3 C CH CH 2 B. HC C CH

44 Solution Write the IUPAC name for the following compounds. A. B. C CH CH 2 HC C CH Step 1 Name the longest carbon chain that contains the double or triple bond. A. B. C CH CH 2 HC C CH pentene butyne

45 Solution Write the IUPAC name for the following compounds. A. B. C CH CH 2 HC C CH Step 2 Number the main chain from the end nearer the double or triple bond. CH A. C CH CH B. HC C CH CH pentene 1-butyne

46 Solution Write the IUPAC name for the following compounds. A. B. C CH CH 2 HC C CH Step 3 Give the location and name of each substituent (alphabetical order) as a prefix to the alkene or alkyne name A. C CH CH 2 B. 5 2-methyl-2-pentene HC C CH methyl-1-butyne

47 Learning Check Draw the condensed structural formula for each of the following. A. 2-hexyne B. 3-methyl-3-hexene

48 Solution Draw the condensed structural formula for each of the following. A. 2-hexyne B. 3-methyl-3-hexene

49 Cis and Trans Isomers Cis and trans isomers have the same formula, but different physical and chemical properties. occur because double bonds in alkenes are rigid and cannot rotate. We add the prefix cis or trans to denote whether the atoms bonded to the carbon atoms are on the same side or the opposite sides of the double bond.

50 Cis Trans Isomers Cis trans isomers occur when different groups are attached to the carbon atoms in a double bond. In a cis isomer, groups are attached on the same side of the double bond. In the trans isomer, the groups are attached on opposite sides of the double bond.

51 Cis Trans Isomerism Cis trans isomers do not occur if one of the carbon atoms in the double bond has identical groups. (neither cis nor trans) (neither cis nor trans)

52 Naming Cis Trans Isomers The prefixes cis- or trans- are placed in front of the alkene name when there are cis trans isomers. cis- trans- Br Br Br H C C C C H H H Br cis-1,2-dibromoethene trans-1,2-dibromoethene

53 Alkenes: Drawing Cis Trans Isomers Draw the cis and trans isomers of 2-hexene. We start by drawing the condensed structural formula. Because two different groups are attached to each carbon on the double bond, we can draw cis and trans isomers for this compound.

54 Alkenes: Drawing Cis Trans Isomers Draw the cis and trans isomers of 2-hexene.

55 Learning Check Name each, using cis trans prefixes when needed. Br A. C C H Br H H B. H C C Cl C. C C H Cl

56 Solution Name each, using cis trans prefixes when needed. Br Br A. H C C H cis-1,2-dibromoethene H B. H C C trans-2-butene Cl C. H C C Cl 1,1-Dichloropropene Identical atoms; no cis or trans

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