Review One

Review Topics… Going over Online Practice Exam (Please turn in a copy). Topics for Exam Multiple Choice Questions

Practice Exam One

Other topics or Questions?  Isomers Functional groups Melting/boiling points Cis/trans in cycloalkane rings & double bonds

Isomers… Draw any isomer of decane in the space below (just not n-decane)…(or draw in your composition books)…

Possible isomers… The easiest one for me to do is to draw 1 fewer carbons in the “main” chain, and then add a methyl somewhere… Key is to keep the number of carbons at 10!  (and of course, the hydrogens at 22).

Functional Groups… Draw a ketone in your composition book… What is this type of functional group?

Draw a ketone in your composition book… Remember they contain a carbonyl with two carbons attached… What is this type of functional group? This is an ether…

Melting Point/Boiling Point Rank the following in terms of decreasing boiling point (i.e. highest on the left side)… ______ > ______ > ______ > ________

C & D have 8 carbons, D is higher b/c it is a straight chain. A has 5 carbons and B only 4, so A is higher than B. __d____ > ___c___ > __a____ > _____b___

Naming (emphasizing cis & trans)… Name the following compound Draw trans-2-heptene

answers… Name the following compound This is cis-1-fluoro-4-methyl cycloheptane Draw trans-2-heptene

Exam Setup Multiple choice Questions (please bring a green scantron) Short Answer Questions (drawing structures, giving names, etc.). Reaction Page (6-7 reactions where you draw in the reagent or product).

Multiple Choice Questions (time permitting)

1. All except which of the following are formulas of organic compounds? a) C4H10 b) CH3CH2OH c) KCl d) CH3CH2Cl © 2013 Pearson Education, Inc.

1. All except which of the following are formulas of organic compounds? a) C4H10 b) CH3CH2OH c) KCl d) CH3CH2Cl © 2013 Pearson Education, Inc.

2. The simplest hydrocarbon is _______. a) CH2 b) CH4 c) C2H4 d) C2H6 © 2013 Pearson Education, Inc.

2. The simplest hydrocarbon is _______. a) CH2 b) CH4 c) C2H4 d) C2H6 © 2013 Pearson Education, Inc.

3. The raw material from which most hydrocarbons are obtained is _______. a) gasoline b) petroleum c) animal fats d) vegetable oils © 2013 Pearson Education, Inc. 40

3. The raw material from which most hydrocarbons are obtained is _______. a) gasoline b) petroleum c) animal fats d) vegetable oils © 2013 Pearson Education, Inc. 41

4. The IUPAC name for the following alkane is _______. a) 2,3-dimethylpentane b) 3-ethyl-2-methylbutane c) 3,4-dimethylpentane d) 2-methyl-3-ethylbutane © 2013 Pearson Education, Inc.

4. The IUPAC name for the following alkane is _______. a) 2,3-dimethylpentane b) 3-ethyl-2-methylbutane c) 3,4-dimethylpentane d) 2-methyl-3-ethylbutane © 2013 Pearson Education, Inc.

5. Which is NOT a gas? a) methane b) ethene c) acetylene d) octane 44 © 2013 Pearson Education, Inc. 44

5. Which is NOT a gas? a) methane b) ethene c) acetylene d) octane 45 © 2013 Pearson Education, Inc. 45

Compounds comprised of the same number and kinds of atoms, but different in their atomic arrangement are known as_______. a) isotopes b) isomers c) homologs d) allotropes © 2013 Pearson Education, Inc.

Compounds comprised of the same number and kinds of atoms, but different in their atomic arrangement are known as_______. a) isotopes b) isomers c) homologs d) allotropes © 2013 Pearson Education, Inc.

7. The one element necessarily present in every organic compound is_______. a) hydrogen b) oxygen c) carbon d) nitrogen © 2013 Pearson Education, Inc. 48

7. The one element necessarily present in every organic compound is_______. a) hydrogen b) oxygen c) carbon d) nitrogen © 2013 Pearson Education, Inc. 49

8. In the name cyclohexane, the prefix “cyclo-” means that_______. a) the compound is explosive b) the carbon atoms are joined in a ring c) the compound is a derivative of benzene d) the carbons have a valence of three © 2013 Pearson Education, Inc. 50

8. In the name cyclohexane, the prefix “cyclo-” means that_______. a) the compound is explosive b) the carbon atoms are joined in a ring c) the compound is a derivative of benzene d) the carbons have a valence of three © 2013 Pearson Education, Inc. 51

9. How many compounds having the formula C3H8 are possible? a) one b) two c) three d) four © 2013 Pearson Education, Inc.

9. How many compounds having the formula C3H8 are possible? a) one b) two c) three d) four © 2013 Pearson Education, Inc.

10. The IUPAC name for the following cycloalkane is_______. a) 3-bromo-4-chlorocyclopentane b) 1-bromo-2-chlorocyclopentane c) 3-chloro-4-bromocyclopentane d) 4-chloro-3-bromocyclopentane © 2013 Pearson Education, Inc.

10. The IUPAC name for the following cycloalkane is_______. a) 3-bromo-4-chlorocyclopentane b) 1-bromo-2-chlorocyclopentane c) 3-chloro-4-bromocyclopentane d) 4-chloro-3-bromocyclopentane © 2013 Pearson Education, Inc.

11. Which is NOT an appropriate name for CH2=CH-Cl? a) chloroethylene b) chloroethene c) methylene chloride d) vinyl chloride © 2013 Pearson Education, Inc. 56

11. Which is NOT an appropriate name for CH2=CH-Cl? a) chloroethylene b) chloroethene c) methylene chloride d) vinyl chloride © 2013 Pearson Education, Inc. 57

12. If octane and water are mixed, the result is_______. a) an emulsion b) a clear solution of hexane dissolved in water c) a layer of octane sitting on top of a layer of water d) a layer of water sitting on top of a layer of octane © 2013 Pearson Education, Inc.

12. If octane and water are mixed, the result is_______. a) an emulsion b) a clear solution of hexane dissolved in water c) a layer of octane sitting on top of a layer of water d) a layer of water sitting on top of a layer of octane © 2013 Pearson Education, Inc.

13. In ethylene, the two carbons are joined by a(n)_______. a) single bond b) double bond c) triple bond d) ionic bond © 2013 Pearson Education, Inc.

13. In ethylene, the two carbons are joined by a(n)_______. a) single bond b) double bond c) triple bond d) ionic bond © 2013 Pearson Education, Inc.

1. Which compound does not contain a double bond? propylene butene acetylene cyclohexene © 2013 Pearson Education, Inc.

1. Which compound does not contain a double bond? propylene butene acetylene cyclohexene © 2013 Pearson Education, Inc.

3. The IUPAC name for the following compound is_______. ethylcyclopentene 1-ethylcyclopentene 3-ethylcyclopentene 4-ethylcyclopentene © 2013 Pearson Education, Inc.

3. The IUPAC name for the following compound is_______. ethylcyclopentene 1-ethylcyclopentene 3-ethylcyclopentene 4-ethylcyclopentene © 2013 Pearson Education, Inc.

4. Restricted rotation around double bonds results in_______. structural isomerism geometric isomerism stereoisomerism fused ring compounds © 2013 Pearson Education, Inc.

4. Restricted rotation around double bonds results in_______. structural isomerism geometric isomerism stereoisomerism fused ring compounds © 2013 Pearson Education, Inc.

1-bromopropane butene diethyl ether phenol 5. Which of the following molecules would you expect to be capable of possessing geometric isomers? 1-bromopropane butene diethyl ether phenol © 2013 Pearson Education, Inc. 68

1-bromopropane butene diethyl ether phenol 5. Which of the following molecules would you expect to be capable of possessing geometric isomers? 1-bromopropane butene diethyl ether phenol © 2013 Pearson Education, Inc. 69

structural cis trans stereo 6. An isomer that has the substituents located on the same side of a double bond is said to be a _______ isomer. structural cis trans stereo © 2013 Pearson Education, Inc. 70

structural cis trans stereo 6. An isomer that has the substituents located on the same side of a double bond is said to be a _______ isomer. structural cis trans stereo © 2013 Pearson Education, Inc. 71

2-heptyne 2-pentene pentane cyclopentene 7. The name of the product in the following equation is_______. 2-pentyne + 2H2  2-heptyne 2-pentene pentane cyclopentene © 2013 Pearson Education, Inc.

2-heptyne 2-pentene pentane cyclopentene 7. The name of the product in the following equation is_______. 2-pentyne + 2H2  2-heptyne 2-pentene pentane cyclopentene © 2013 Pearson Education, Inc.

Br CH3CHCH2CH3 CH3CH=CHCH3Br CH3CHCH2CH3Br CH3CH=CCH3 8. The product for the following reaction using Markovnikov’s rule is_______. CH3CH=CHCH3 + HBr  Br CH3CHCH2CH3 CH3CH=CHCH3Br CH3CHCH2CH3Br CH3CH=CCH3 © 2013 Pearson Education, Inc.

8. The product for the following reaction using Markovnikov’s rule is_______. CH3CH=CHCH3 + HBr  CH3CH=CHCH3Br CH3CHCH2CH3Br CH3CH=CCH3 © 2013 Pearson Education, Inc.

9. Addition reactions are characteristic of_______. alkanes alkenes alkynes aromatics © 2013 Pearson Education, Inc.

9. Addition reactions are characteristic of_______. alkanes alkenes alkynes aromatics © 2013 Pearson Education, Inc.

10. The IUPAC name for the following compound is_______. 1-chloro-2-methylbenzene 2-chlorotoluene 2-methyl-1-chlorobenzene 6-chlorotoluene © 2013 Pearson Education, Inc.

10. The IUPAC name for the following compound is_______. 1-chloro-2-methylbenzene 2-chlorotoluene 2-methyl-1-chlorobenzene 6-chlorotoluene © 2013 Pearson Education, Inc.

11. Benzene and its derivatives are commonly known as_______. cycloalkanes cycloalkenes cycloalkynes aromatics © 2013 Pearson Education, Inc.

11. Benzene and its derivatives are commonly known as_______. cycloalkanes cycloalkenes cycloalkynes aromatics © 2013 Pearson Education, Inc.

12. Two adjacent substituents on a benzene ring are said to be_______. 1,1-disubstituted ortho to one another meta to one another para to one another © 2013 Pearson Education, Inc.

12. Two adjacent substituents on a benzene ring are said to be_______. 1,1-disubstituted ortho to one another meta to one another para to one another © 2013 Pearson Education, Inc.

13. If two positions on a benzene ring are substituted, how many isomers are possible? one two three four © 2013 Pearson Education, Inc. 84

13. If two positions on a benzene ring are substituted, how many isomers are possible? one two three four © 2013 Pearson Education, Inc. 85