Organic Chemistry Chapter Assignment & Problem Set

Organic Chemistry Chapter 25-26 Assignment & Problem Set Name_____________________________ Warm-Ups (Show your work for credit) Date______________ A...
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Organic Chemistry Chapter 25-26 Assignment & Problem Set

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Organic Chemistry Chapter 25-26 Assignment & Problem Set Study Guide: Things You Must Know Vocabulary (know the definition and what it means):  organic chemistry  hydrocarbon  alkane, alkene, alkyne  homologous series  alkyl group  branched hydrocarbon  saturated vs. unsaturated hydrocarbon  structural isomer  functional group  halocarbon  alcohol  ether

           

aldehyde ketone organic acid (carboxylic acid) ester amine amide substitution reaction addition reaction fermentation esterification oxidation polymerization

Learning Objectives (you should know:)  organic chemistry is the study of carbon compounds.  how to name, write molecular formulas, and draw structural formulas for alkane, alkene, and alkyne hydrocarbons, including branched hydrocarbons with alkyl groups.  hydrocarbons form homologous series of compounds with physical and chemical properties that change in a gradual and predictable way.  hydrocarbons are nonpolar molecules held together by weak dispersion forces, and they do not dissolve in water (“like dissolves like”).  alkanes are saturated hydrocarbons and alkenes and alkynes are unsaturated hydrocarbons.  how to draw structural isomers of organic compounds.  burning natural occurring hydrocarbons (coal, petroleum, and natural gas) releases large amounts of energy. The amount of energy released can be calculated using Table I.  a functional group is a reactive group of atoms attached to a carbon chain, and each type of functional group gives special chemical and physical properties to the molecule.  how to recognize the nine functional groups on Table R, and how to name and write structural formulas for compounds containing those functional groups.  how to predict products, write balanced equations, and name compounds for the following chemical reaction classes: substitution, addition, fermentation, esterification, oxidation, and polymerization. Reference Tables you should know how to interpret:  Table I: Heats of Reaction at 101.3 kPa and 298 K  Table P: Organic Prefixes  Table Q: Homologous Series of Hydrocarbons  Table R: Organic Functional Groups

Organic Chemistry Chapter 25-26 Assignment & Problem Set

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•Read Chapter 25 & 26. Skip “geometric isomers & stereoisomers” pp 754-756. •Regents only extra credit assignment (due anytime before the test): Gasoline is a mixture of many different hydrocarbons. Find out what the components of gasoline are. Compile your results in a well-organized table that lists the name, molecular formula, structural formula, and boiling point of each of the component hydrocarbons. You can receive one point for each complete entry, up to a maximum of 20 points. Lab 26: Hydrocarbons Lab 27: Esterification •Regents Tables Table P: Organic Prefixes Table Q: Homologous Series of Hydrocarbons Table R: Organic Functional Groups •Warm-ups and problems will be collected before you take the test. Answer all problems in the space provided. For problems involving an equation, carry out the following steps: 1. Write the equation. 2. Substitute numbers and units. 3. Show the final answer with units. There is no credit without showing work. Alkanes 1. How many valence electrons does carbon have? What is the geometry of the bonding electrons around methane?

2. What is a homologous series? Why are the alkanes such a series?

3. If the boiling point of hexane is 68oC and the boiling point of octane is 126oC, estimate the boiling point of heptane. If the actual boiling point of heptane is 98oC. What is the percent error of your estimate.

4. Name and draw the structural formulas and condensed structural formulas for the alkyl groups derived from methane, propane and butane.

5. Name these alkanes and write their molecular formulas. a. CH3CH2CH3 b. CH3CH2CH2CH2CH2CH3

Organic Chemistry Chapter 25-26 Assignment & Problem Set 6. Name the following hydrocarbons. A. B. C. E. F. G.

7. Draw condensed structural formulas for these compounds: a. 3-ethylpentane b. 2,4-dimethylhexane

8. Draw the following condensed structural formulas and state why the names are incorrect. What are the correct names? a. 2-dimethylpentane b. 1,3-dimethylpropane

9. Why are alkane molecules nonpolar?

10. What intermolecular force(s) hold hydrocarbons together in the liquid and solid state? Why do the melting points of the alkanes increase with increasing molar mass?

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Organic Chemistry Chapter 25-26 Assignment & Problem Set Alkenes and Alkynes 11. Differentiate between unsaturated and saturated hydrocarbons. Give an example of each.

12. Draw the structural formulas for a. 1-butene

b. 2-butene

c. ethyne

13. Draw the condensed structural formula for 4-methyl-2-pentene. What is its molecular formula?

Isomers 14. Draw the carbon backbone formulas for all compounds with the molecular formula C5H10. Name each compound.

15. Draw a carbon backbone for each of the following alkenes. State the molecular formula of each. a. 2-pentene b. 2-methyl-2-pentene c. 2-ethyl-2-pentene

Naturally Occurring Hydrocarbons 16. What are the names of the three naturally occurring states (S, L, G) of fossil fuel? For the fossil fuel that is a gas, what are the hydrocarbon components?

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Organic Chemistry Chapter 25-26 Assignment & Problem Set Functional Groups 17. What is a functional group?

18. Circle the functional group in each structure, name the functional group, and name each compound. a. CH3-OH b. CH3-CH2-NH2

a. CH3-CH2-COH

d. CH3-CH2-CH2-Br

O

e. CH3-CH2-O-CH2-CH3

19. Name the following halocarbons. a. CH3CH2Cl

b. CH3CHCH=CH2 Cl

20. Name the following alcohols. a. CH3CH2CHCH2CH3

b. CH3CHCH3

O-H

O-H

21. What is a carbonyl group? Draw the carbonyl groups that are characteristic of aldehydes, ketones, carboxylic acids, and esters.

22. Name the following aldehydes and ketones: a. CH3CH2C=O b. CH3CH2CH2CCH2CH3 H

O

c. CH3CH2CH2CH2C=O H

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Organic Chemistry Chapter 25-26 Assignment & Problem Set 23. Name the following ethers: a. CH3OCH2CH3

b. CH3CH2CH2OCH3

24. Give the name of each carboxylic acid. (Note: these organic acids are written so that –COOH represents –COH.) O a. HCOOH b. CH3COOH

c. CH3CH2COOH

d. CH3CH2CH2COOH

25. Show that ethyl methyl ether and 1-propanol are structural isomers.

Organic Reactions 26. What is a substitution reaction? Write a substitution reaction for mixing propane and bromine.

27. What is an addition reaction? Give an example of a “hydration” addition reaction (reaction with water) and a “hydrogenation” addition reaction (reaction with hydrogen gas) using ethene.

Hydration:

Hydrogenation:

28. Write a balanced equation for the reaction of 2-butene with hydrogen bromide.

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Organic Chemistry Chapter 25-26 Assignment & Problem Set 29. What reactants are needed to make the ester: propyl ethanoate? Write a chemical reaction.

30. Write an equation for the reaction of ethanol and butanoic acid.

31. Write a balanced equation for the complete combustion of pentane. What other products would be formed if combustion were incomplete?

32. Write an equation for the complete combustion of octane, C8H18.

33. For the following reactions, predict the products, name all the chemicals, and balance the equation. a. ethane + chlorine gas 

b. 2-hexene + chlorine gas 

c. 2-butene + water 

d. ethanol + propanoic acid 

34. In organic reactions, each set of reactants is a clue to knowing the reaction class and predicting products. For these classes, what are the general types of reactant compounds?  Substitution • Addition 

Esterification



Combustion

Organic Chemistry Chapter 25-26 Assignment & Problem Set

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Organic Chemistry Chapter 25-26 Assignment & Problem Set

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Polymerization 35. What is a polymer? A monomer?

36. Give names and uses for three types of polymers.

Properties of Organic Compounds 37. Propane (CH3CH2CH3) and acetaldehyde (ethanal) (CH3CHO) have the same molar mass, but propane boils at -42oC and acetaldehyde boils at 20oC . Account for this difference.

38. Explain why 1-butanol has a higher boiling point than diethyl ether. Which compound would you expect to be more soluble in water?

Review 39. Calculate the pH of the following aqueous solutions a. [OH-] = 1.0 x 10-4 M b. [H+] = 1.0 x 10-4 M

40. Give the oxidation number of each element in sodium sulfate.

41. An aqueous solution of unknown pH turns blue when tested with bromthymol blue and turns colorless when tested with phenolphthalein. What is the pH range of the solution?

42. Calculate the molarity of a solution made by adding 27 g of calcium nitrate to water so that the final volume of the solution is 350 mL.

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