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1 H 223 Worksheet 9 Notes Oregon State University 1. Draw a primary alcohol and name it. OH 1-propanol Note: A primary alcohol has the form RH 2 OH; a secondary alcohol has the form R 2 H OH; and a tertiary alcohol, the form R 3 OH. The R groups do not need to be the same. Draw a secondary alcohol and name it. OH 2-propanol Draw a tertiary alcohol and name it. OH 2-methyl-2-propanol 2. Draw and label the cis- and trans- isomers of 2-butene. cis- and trans--2-butene 3. Draw and label the cis- and trans- isomers of 3-pentene.[Should be named 2- pentene] cis- and trans--2-pentene
2 4. What is the systematic (IUPA) name for the following compound? trans-3-hexene Does the above compound have a geometric isomer (cis-/trans-)? Yes, the cis- isomer. 5. What is the systematic (IUPA) name for the following compound? 3-ethyl-2-methyl-2-pentene Does the above compound have a geometric isomer (cis-/trans-)? No. 6. What is the product produced from the addition of H to 1-butene? What is meant by Markovnikov's Rule? The hydrogen adds to the carbon with the most hydrogens already.
3 7. What is the product produced from the addition of H to 2-butene? 8. What is the product produced from the addition of H to 1-butyne? 9. Draw an aldehyde that contains six carbon atoms. Identify the carbonyl group (=O) portion in the molecule. 10. What is the molecular formula for the following four structures? What are the systematic names for these cyclic compounds? All have the molecular formula 6 H Structures (A) and (D) are o-dibromocyclohexane. Structure (B) is m-dibromocyclohexane. Structure () is p-dibromocyclohexane. (A) (B) () (D)
4 11. What is the product produced from the addition of H to 1-butene? What is meant by Markovnikov's Rule? The hydrogen adds to the carbon with the most hydrogens already. 12. The molecule shown below is: (A) (B) () (D) (E) an aldehyde. a ketone. a carboxylic acid. an amine. all of the above. 13. The molecule shown below is: (A) (B) () (D) (E) an aldehyde. a ketone. a carboxylic acid. an amine. all of the above. 14. What is meant by a condensation reaction? Give an example. Water is lost during a condensation reaction. Examples include: the formation of an ester from an alcohol and a carboxylic acid, the formation of an amide from an amine and a carboxylic acid.
5 15. What is meant by an addition reaction? Give an example. Addition is to make an addition to a molecule. An example is the addition of a small molecule (such as 2 ) to an alkene. propene + 2 (in UV) 1,2-dibromopropane 16. What is chiral? Sketch a molecule that contains three chiral carbons. A molecule is chiral if it cannot be superimposed on its mirror image. A carbon in a molecule is chiral if it has four different groups attached to it. H 2 is not chiral. H is. 17. What polymer is formed by the reaction of a radical initiator and ( 6 H 5 ) 2? -[-( 6 H 5 ) 2 -] n - The radical initiator breaks the pi-bond in the monomer causing it to become a larger radical and attacking another monomer unit. R + R monomer initiator new, larger, radical (The dot inside the right carbon is to represent the radical electron) (This new radical will attack a monomer unit and this process will continue...)
6 18. What polymer is formed by the reaction of HOOH 2 H 2 H 2 OOH and H 2 NH 2 H 2 H 2 H 2 NH 2? This is a condensation polymerization. Water is lost between the amine and carboxylic acid: H H O O HNH 2 H 2 H 2 H 2 NH + HOH 2 H 2 OH water will leave H H O O HNH 2 H 2 H 2 H 2 NH 2 H 2 OH new amide The carboxylic acid group on the right is still in tact and will react with an amine group from another H 2 NH 2 H 2 H 2 H 2 NH 2 molecule. The amine group on the left is still in tact and will react with a carboxylic acid group from another HOOH 2 H 2 OOH molecule. 19. Show the mechanism for: + in the presence of Al 3 (This is an Aromatic Electrophilic Substitution reaction) Aromatic: ragrant; chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. It can also be considered a manifestation of cyclic delocalization and of resonance Electrophilic: Electron-lover is a reagent attracted to electrons Substitution: One or more hydrogen atoms of a core structure have been replaced with a functional group atalyst: Species which increases the rate of a reaction without being consumed
7
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