Total

PRINTEDNAME(Last, First) ______________ ____________ ________ __

Question (Points) I (30) II (12) III (8) IV (14) V (6) VI (10) VII (10) VIII (10)

Score

CHEMISTRY 2261 EXAM 1

Last 4 digits of ID#_____________ February 24, 2010

This examhas 8 printedpagesof questions. Checknowto makesureyou haveall 8 pages. Makesureto print your namein capsand last 4 digitsof yourstudentID# above . Useonly ballpointor ink pen for final answers. Writeclearlyin the spacesprovided,use backpagesonly for scratchwork. This examis wortha total of 100 points. I. MultipleChoice(3 pt each, 30 pt total). Writedownthe answersin the box at the bottomof the page. 1. Whichof the followingis the strongestacid?

2. Whichof the followingis the weakestbase?

3. Whichof the followingmoleculeshas the lowestboilingpoint?

4. Whichof the followingmoleculeshas the largestbondanglearoundthe central atom? 1

5. Whichof the followinghas a net dipolemomentof zero?

Problem # Answer

10

6. Whichof the followingmoleculesis a Lewisacid?

7. Fromthe Lewisstructuresgivenbelow,selectthe only valid representationof CH3N3.

8. Whichof the followingstructuredepictsthe moststableconformationof cis-1-isopropyl3-methylcyclohexane?

9. Whichof the followingstructuresis 2-isopropyl5-methyl-cycloyhexanol?

10. Whichoneis the correctIUPACnamefor the followingcompound? 2

(A) 6-chloro3-isopropylN-methyl7-heptamine (B) 2-chloro5-isopropylN-methylheptamine (C) 2-chloro5-ethyl-N,6-dimethylheptamine (D) 3-chloro6-isopropylN-methylheptamine (E) 3-chloro6-ethyl-N,7-dimethylheptamine

II. Fill in the box with the correctanswerthat best describethe relationshipof the followingpairsof molecules(12 pt). (A) Constitutional isomers (B) Conformers (D) Identical structures (E) Unrelated (C) Stereoisomers

III. (a) Drawthe bondline structuresof all five constitutionalisomersof hexane(C6H14) (5pt).

(b) Drawthe bondline structuresof all four possiblecyclicconstitutionalisomerswhosemolecular formulas are C5H10 (3pt).

IV. For simplicity, lonepair electronsare oftenleft out in the bondline structureof a molecule.(a) Fill in the lonepair electronswhereneededin the givenstructure.(b) Write downthe correctorbital hybridizationof the arrowpointedatomsin the boxesgivenbelow(14 pt):

atom hybridization

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V. The followingbondline structuredepicts1-chloropropane.Completethe followingNewman projectionslookingdown1 and2 C-C bond(6 pt):

I) The most stable staggered conformation of 1-chloro-propane.

II) The least stable eclipsed conformation of 1-chloro-propane

VI. (a) Completethe Lewisstructuresof the followingunchargedcompoundsby addingall the nonbondingelectrons,multiplebondsand any necessarynon-zeroformalcharges(4 pt).

(b) Drawthe 3-D structuresof CH3-, BF3 andCH2Cl2 usingwedgesanddashesto indicatein-planeand out-of planebonds. Predict(circle)whichmoleculeswill havea moleculardipolemoment(6 pt).

VII. For the following substituted cyclohexane, draw both possible chair conformations and indicate (circle)whichconformationis morestableor whetherbothare equallystable(10 pt).

VIII. (a) Interconvertthe IUPACnamewith the bondline structurefor the followingmolecules(10 pt): 7

PeriodicChart
I H Li Na Be Mg B Al C Si N P O S F Cl Br II III IV V VI VII