CHEM&152 Spring 2009 ORGANIC STRUCTURES, SHAPES AND ISOMERISM

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1 EM&152 Spring 2009 ORGANI STRUTURES, SAPES AND ISOMERISM Fill-in Date Stamp here Name Partner Lecturer: Discussion In this experiment you will use molecular models to construct 3-dimensional models of organic compounds. You will then represent these models on the paper by writing structural formulas. Structural formulas are more complete than molecular formulas, since they indicate the position of attachment of each atom, and the type of bond formed. The molecular models you construct should give you a better visual understanding of the 3-dimensional nature and spatial relationships that occur in organic molecules, and it is hoped that your understanding of the concept of "isomers" will be enhanced. Your molecular model kit consists of atoms represented as plastic balls that have been drilled to receive connecting bonds. The atoms are colored to represent the different atoms commonly found in organic compounds. All single bonds are represented by placing a short-length (hard) gray plastic stick between the 2 atoms. Unsaturated (double and triple bonds) linkages (or highly strained linkages) require the use of long-length (flexible) gray plastic sticks. The following color identification scheme is used for the models you will be working with: = black; = white; l = green; N = blue; O = red The IUPA naming system The IUPA naming system was developed to provide a systematic method of naming organic compounds. It is designed with the following fundamental principle: each different compound should have a different name. This discussion will provide a brief introduction to the IUPA system. 1. Each IUPA name consists of several parts: 3-D relationship, numbered substituents, the number of carbons in the longest chain and an ending (suffix) indicating functional groups (base name). 2. ount the number of carbons in the longest, continuous chain; this may or may not be equal to the total number of carbons in the structure. This gives you the base name, which has a root name based on the number of carbons (See Table 1) and one of the following endings: -ane: all - single bonds -ene: one - double bond -yne: one - triple bond. 3. Number the carbon chain. You can number from left to right, or right to left; however the substituents (groups coming off of the chain) should have the lowest possible numbers. 4. Name the substituents as alkyl groups, with a number in front giving the location of this group. An alkyl group name typically consists of the prefix, based on the number of s in the group, and the suffix yl. alogens get a slightly different name: chlorine becomes chloro, bromine becomes bromo. Substituent names are listed in alphabetical order, not numerical order. This part of the name comes before the root name of the longest chain. 5. When two or more substituents are identical, they are listed together. Indicate this by the use of the prefixes di-, tri-, tetra-, etc. Give each substituent its own number. 6. Use hyphens to separate numbers and letters, commas to separate numbers. hemistry&152 Rev Sp09AEM Spring 2009 Page 1 of 15

2 Some examples: note: there are several different ways to draw structures. You can have expanded structures, and condensed structures. Structures are generally drawn in a linear fashion for ease, but remember that a - single bond does not have an angle of 180 o but instead an angle of o. For that reason, it is easier to draw the structures in a line, but note the two examples below for the same structure. 3 3 l 2 3 A more condensed linear structure and an expanded structure with correct bond angles. Both represent the molecule: 2-methyl-3-chloro pentane (prefix substituents) root (5 carbon chain) suffix (ane for all - single bonds) 3 l , 3, 3-trimethylhexane Table 1: The root names for 1 through 10 for hydrocarbon groups are listed below, and should be memorized. The Experiment carbon # root carbon # root 1 meth- 6 hex- 2 eth- 7 hept- 3 prop- 8 oct- 4 but- 9 non- 5 pent- 10 dec- A. The Tetrahedral arbon Atom 1. Examine one of the carbon atoms. ow many holes are found in the model carbon atom? 2. Insert a short gray stick into each hole of the carbon atom. What do these sticks represent? 3. ow many covalent bonds are necessary for each carbon atom in an organic molecule? #1 Organic Structures Rev Sp09AEM Spring 2009 Page 2 of 15

3 4. What is the ideal bond angle represented by any pair of sticks in a carbon with only single bonds; note that all pairs of sticks have identical bond angles. 5. What causes these bonds to be symmetrically arranged about the carbon atom? B. Alkanes and Alkyl Groups. Alkanes are hydrocarbon compounds containing only single bonds. These are considered saturated. They are named according to the longest continuous chain of carbon atoms. 1. onstruct a model of a methane molecule by adding a hydrogen (white ball) to each of the 4 bonds in your carbon model. Draw the structural (2-dimensional) formula represented by this model. This 1-carbon group is called methane, and is the simplest alkane. It, and all alkanes, follow the generic formula of n (2n + 2), where n represents the number of carbon atoms in the longest continuous chain. 2. Remove one of the hydrogens (the white ball) -but not the bond/stick- from your methane model. This is the simplest example of an alkyl group. Draw the structural formula for this group. Alkyl groups are carbon containing chains or groups that are connected to a longer carbon chain. This 1-carbon group is called a methyl group, and has the formula - 3. Alkyl groups of larger carbon number have the general formula of n (2n + 1). This is the simplest of the alkyl groups. Alkyl groups are named by using the root indicating the number of carbons in the group and adding -yl to the root. a. What is the name for a 5-carbon straight chain alkyl group? b. What would be the formula for an ethyl group (2 carbon atoms)? c. Draw the structural formula for the ethyl group #1 Organic Structures Rev Sp09AEM Spring 2009 Page 3 of 15

4 d. onstruct a model of this ethyl group. Rotate the molecule by grasping one methyl group in each hand. Is free rotation about a single bond possible? Yes e. Place a white ball (hydrogen) on the structure so that all bonds are connected to atoms (2 carbons, and 6 hydrogens total). Rotate the molecule until the hydrogens are in a "staggered" arrangement. Rotate the molecule again until the hydrogens are directly over each other (eclipsed). This representation of ethane is called a Newman Projection. No staggered eclipsed Reference: f. Which conformation (form) would you predict would be favored? (Remember that the sticks represent negatively charged electron pairs.) g. Are all six hydrogens of the ethane molecule chemically equivalent? Yes No 3. Remove a hydrogen from ethane, and unite the ethyl group with a methyl group. Draw the structural formula for this new hydrocarbon. a. What is the molecular formula for this new compound? b. What is the name of this compound? c. Examine the arrangements of hydrogen atoms in this new model. Remove a hydrogen from the end carbon. Examine the structure. Replace it. Remove a hydrogen from the other end carbon. Examine the structure. ow are those two structures related - are they all chemically equivalent (meaning, are they the same structure or different)? Yes they are equivalent No, they are different structures d. Now remove a hydrogen from the end carbon, examine the structure. Replace it. Remove a hydrogen from the middle carbon, examine the structure. Replace it. ow are those two structures related are they chemically equivalent (aka the same)? Yes they are equivalent No, they are different structures #1 Organic Structures Rev Sp09AEM Spring 2009 Page 4 of 15

5 4. Straight chain alkanes all have the formula n (2n+2). They are all named by finding the longest continuous carbon chain and following the nomenclature system of : prefix-root-ane. Prefixes will be used if there are substituents (anything other than hydrogen) bonded to the main chain; root represents the number of carbons in the longest chain and -ane indicates that the structure is comprised only of carbon-carbon single bonds. Using this information, draw the following structures: a. Butane: b. Pentane: c. Octane: And name the following structures: a b Now try a few with substituents (side chain groups) a. 2-methyloctane b. 3-ethylnonane 5. Atoms other than carbon and hydrogen can be bonded to carbon atoms. From a 2-dimensional drawing of dichloromethane ( 2 l 2 ) it appears that two different dichloromethanes exist. l l l and l onstruct a model of dichloromethane by replacing 2 of the white balls on methane with green balls. What does your 3-dimensional model tell you about the "equivalency" of the 2- dimensional models of dichloromethane shown above? (circle your answer below) They are equivalent/the same structure They are different structures Briefly explain your circled answer: #1 Organic Structures Rev Sp09AEM Spring 2009 Page 5 of 15

6 . Isomerism Isomers (iso = same; mer = part) are compounds that have the same molecular formulas but differ in either position/connectivity (structural isomer) or 3-dimensional shape (geometric isomer) of attachment. Molecules are not isomers if they can be turned into one another without breaking any bonds. 1. Join 4 carbon atoms together by short single bonds then fill out the structure by adding hydrogen atoms. a. Is it possible to do this in more than one way? b. Draw 2 different structural formulas for a compound containing four carbons and 10 hydrogens. c. ow do the molecular formulas for these two compounds compare? d. What term is used to describe compounds with the same molecular formula but different structural formulas (circle the correct term)? Structural isomer Geometric isomer 2. There are three possible structural isomers of pentane ( 5 12 ). Use your model kit to determine these structures and draw structural formulas for these isomers. 3. There are many other examples of isomerism in organic chemistry. onstruct models and draw the four structural isomers of dichloropropane ( 3 6 l 2 ). #1 Organic Structures Rev Sp09AEM Spring 2009 Page 6 of 15

7 D. ycloalkanes - ydrocarbon compounds arranged in circles. 1. onstruct a model of cyclopropane: a. an this be easily done using the short plastic sticks? b. What is the bond angle that results when you force the 3 carbon atoms to bond in this way? (Think triangles!) 2. onstruct a model of cyclobutane: a. What is the bond angle between carbons in this molecule? b. What should the ideal bond angle be for - single bonds? c. Do you think that cyclopropane is stable? Do you think that cyclobutane is stable? (hint: a stable structure is one in which the atoms are not strained in their bonding) 3. onstruct a model for cyclohexane: a. Note that by puckering and buckling, the cyclic structure can have two different structures (conformations), a boat and chair form. Try this with your structure. boat chair #1 Organic Structures Rev Sp09AEM Spring 2009 Page 7 of 15

8 b. Do the bonds in this structure appear strained in any way? Yes No c. What is the approximate bond angle between carbon atoms in this molecule (remember these are all singly bonded carbons!)? d. Would you expect cyclohexane to be more or less stable than cyclopropane? Explain using the concept of bond strain E. Alkenes and is-trans (Geometric) Isomerism. Alkenes are hydrocarbons containing one or more double bonds. They are unsaturated. They are named according to the longest continuous chain of carbon atoms, adding ene to the end, and using a number to indicate the position of the double bonds, if necessary. The simplest alkene is ethene, 2 = 2, also known by the common name, ethylene. 1. Make a model of butane: a. Rotate the single carbon-carbon bonds such that the end methyl ( 3 ) groups are on opposite sides of the center carbons. b. Rotate the single carbon-carbon bonds such that the end methyl groups are on the same side of the center carbons. c. Would the structures you have produced in parts a and b be considered isomers of one another? Explain the basis for your answer. 2. Make a model of cis-2-butene (both methyl groups are on the same side of the double bond). The structural formula for cis-2-butene is shown below: 3 3 = cis-2-butene a. Make another model of trans-2-butene (the end methyl groups are on the opposite sides of the carbon-carbon double bond). #1 Organic Structures Rev Sp09AEM Spring 2009 Page 8 of 15

9 b. an your cis-2-butene model be converted into the trans-2-butene model without breaking bonds? Meaning, can you rotate the carbon atoms around the double bond? Yes No c. Draw the structural formula for trans-2-butene. d. The cis- and trans-2-butenes are called geometric isomers. Why are they given this name? e. Define the term structural isomer and explain how it differs from a geometric isomer. 3. onstruct a model of the benzene molecule from the structural formula. Benzene is probably the most recognizable example of an aromatic hydrocarbon (it has alternating double and single bonds, in a ring), and a specialized alkene. Two different representations of benzene are shown below- the Lewis structure and a shorthand version. a. What is the hybridization and bond angles on each of the carbons in benzene? ybridization = Bond angle = b. Draw the structural formula for 1,3-dimethylbenzene. #1 Organic Structures Rev Sp09AEM Spring 2009 Page 9 of 15

10 4. Indicate whether each of the following compound pairs are geometric isomers, structural isomers, or not isomers at all. Write the names for the compounds under each formula. a. 3 - = - 3 and = 2 and b. Br Br Br and Br and c and d. l l l 3 2 and 3 2 l and #1 Organic Structures Rev Sp09AEM Spring 2009 Page 10 of 15

11 F. Alkynes. Alkynes are hydrocarbons containing one or more triple bonds. They are unsaturated. They are named according to the longest continuous chain of carbon atoms using a number to indicate the position of the triple bonds, if necessary. The simplest alkyne is ethyne,, also known by the common name, acetylene. 1. onstruct a model of 1-butyne and draw its structural formula. 2. onstruct a model of 2-butyne and draw its structural formula. 3. What is the only difference between 1-butyne and 2-butyne? 4. What chemical term describes molecules like 1-butyne and 2-butyne - they are called? G. Other Functional Groups. The behavior of organic molecules is governed by the presence of functional groups, combinations of atoms that act as chemically reactive sites. ompounds with the same functional group will have many similar properties and undergo similar chemical reactions. Double and triple bonds are also functional groups. Build the following molecules. 1. Alcohols-alcohols have the general formula R-O, where R= any alkyl group and the O is called a hydroxy group. (Note: since the O is bonded covalently to a carbon, it does not come off as a hydroxide ion! In other words, this is not an ionic compound.) Again, the longest carbon chain will be the chain that contains the O functional group and the O will always get the lowest number in the molecule. a. onstruct a model then draw the structural formula for 1-propanol, 3 7 O. (The common name is propanol, or propyl alcohol) b. onstruct a model of 3-propanol. Explain why this name is not correct. #1 Organic Structures Rev Sp09AEM Spring 2009 Page 11 of 15

12 c. You most likely left something off your Lewis structure above. What is missing from the oxygen that would complete its octet? (Think back to Lewis Structures) d. onstruct a model, then draw the structural formula for 2-propanol, 3 7 O. (The common name is isopropanol, or isopropyl alcohol). Name the following alcohol, using the examples above: O Ethers have the general formula R-O-R', where R,R' = alkyl groups. a. onstruct a model then draw the structural formula for dimethyl ether, 2 6 O. Ethanol has the same molecular formula. Draw the structure for ethanol Dimethyl ether Ethanol b. What chemical term describes structures like ethanol and dimethyl ether? These structures are called O 3. Aldehydes and ketones have the general formula R groups. For aldehydes, at least one R must be hydrogen. R', where R and R' = alkyl a. onstruct a model then draw the structural formula for the simplest aldehyde, methanal, 2 O. (The common name is formaldehyde). Remember carbon must always have 4 bonds. #1 Organic Structures Rev Sp09AEM Spring 2009 Page 12 of 15

13 b. onstruct a model then draw a structural formula for propanal, 3 6 O. c. onstruct a model then draw the structural formula for the very common ketone, 2- propanone, 3 6 O. (The common name is acetone) d. What chemical term describes structures like propanal and propanone? These structures are called 4. arboxylic acids (OO) have the general formula R O- where R = an alkyl group. When naming a carboxylic acid, the carbon attached to the oxygens is the first carbon in the chain, and the longest chain beginning with that carbon sets the prefix for the name. The e is dropped from the alkane chain name, and oic acid is added. a. onstruct a model, then draw the structural formula for ethanoic acid, 2 4 O 2 (The common name is acetic acid). O b. Now do the same for 3-chloropropanoic acid. c. Acids can be derived from benzene, where the carboxylic acid group (OO) is attached to the benzene ring. onstruct a model for benzoic acid ( 7 6 O 2 or 6 5 OO) and draw it. Then construct a model and draw the structural formula for 4-methylbenzoic acid ( 8 8 O 2 ) Benzoic Acid 4-methylbenzoic acid #1 Organic Structures Rev Sp09AEM Spring 2009 Page 13 of 15

14 O 5. Esters have the general formula R O R' where R, R' = alkyl groups. Esters are named by starting with the alcohol, named as an alkyl group, and then ending with the carboxylic acid, removing the ic acid and replacing it with the suffix -ate. a. The following steps will help you construct a model of ethyl butanoate. b. First: ethyl represents which part of the molecule the alcohol, or the acid? Make this molecule draw it below: c. Second: the butanoate represents which part of the molecule the alcohol, or the acid? Make this molecule draw it below: d. Finally, bring the two molecules together O end to O end. Remove the O from the acid (remove the bond O also) and one hydrogen (white ball only) from the alcohol (leave the bond still attached to the alcohol), connect/bond the remaining molecules together. By the loss of water, you have created an ester! e. onstruct a model then draw the structural formula for ethyl ethanoate, 4 8 O 2. (The common name is ethyl acetate, the smelly stuff in nail polish remover!) #1 Organic Structures Rev Sp09AEM Spring 2009 Page 14 of 15

15 6. Amines have the general formula of R 3 N, where R is any alkyl group or hydrogen. They are named by listing the names of the three alkyl groups, followed by the amine suffix. a. Draw the structure for ammonia, N 3, the simplest amine. b. Again, you probably took a few shortcuts when drawing your N 3 molecule. What did you leave off from your Lewis structure that would complete the octet on the N? c. onstruct a model then draw the structural formula for triethylamine, N( 2 3 ) 3. This compound has a fishy smell. (note the N is attached to groups!) O 7. Amides have the general formula R N. They are formed by combining a carboxylic acid and an amine and removing a water molecule. a. onstruct a model then draw the structural formula for the amide formed when ethanoic acid reacts with ammonia (hint: follow the same procedure for the loss of water that you did when making the ester on the previous page). b. onstruct a model then draw the structural formula for benzamide, 7 7 NO (or 6 5 ON 2 ). #1 Organic Structures Rev Sp09AEM Spring 2009 Page 15 of 15

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