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Chemistry 261 Spring 2010 Exam 1 Ashby

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_______________ (36 points possible) _______________ (36 points possible) _______________ (28 points possible)

TOTAL

_______________ (100 points possible)

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1. Draw the structure for 1-sec-butyl-2-isobutylcyclohexane.

2.

Write the IUPAC name for the following compound.

3.

Write the IUPAC name for the following compound.

4.

Circle the compound with the lowest pKa. a) CH3CH2SH b) CH3CH2NH2 c) CH3CH2OH d) CH3CH2PH2

5.

Write the following reaction using complete Lewis structures, and draw arrows indicating the electron movement for the forward reaction.

HC CH

NH2

HC C

NH3

6. 7.

What is the role of NH3 in the acid base reaction above. ______________________ What is the role of ethyne in the acid base reaction above. _____________________ Write the geometry for each of the following molecules. a) AlCl4 __________________
-

b) C2H2

__________________

8.

Circle the following molecule(s) that is/are polar.

a) BF3

b) CH2CF2

c)

F H

H F

d)

H F

H F

9.

Write the formal charge for each of the following. If the molecule is neutral, write none. *All lone pairs are shown.

a) PCl3
________

b) CCl 3
________

c)

NH3

d) H
_______

O _______

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10. Which of the following statement(s) is/are true regarding contributing resonance structures? a) Each atom in all of the resonance structures must have a complete shell of valence electrons. b) All resonance structures must have the same arrangement of atoms. c) All resonance structures must be valid Lewis structures. d) The resonance structures may have different energies. What is the approximate dihedral angle (0, 60, 120 or 180 degrees) for each of the following? a) cis-1,2-dimethylcyclohexane _______ b) the least stable trans-1,2-dimethylcyclohexane _______ Which atomic orbitals overlap to form the sigma bonding molecular orbital of the indicated C-N bond in the molecule? In which orbitals do you find the designated lone pairs?

11.

12.

(A)

(B)

N H
13.

C orbital = ________ N orbital = ________ (A) lone pair = ________ (B) lone pair = ________

Draw constitutional isomers of the compound shown below *(1) should give a more exothermic combustion and (2) should give a less exothermic combustion reaction.

__________________________ 1) More exothermic isomer 14.

_________________________ 2) Less exothermic isomer

Label the compounds below from the strongest (1) to the weakest (3) base. a) CH3CH2NH ________
-

b) CH3CH2O

c) CH3CH2CH2 ________

________

15.

A sample containing a mixture of enantiomers has a specific rotation of +40. An optically pure R enantiomer has a specific rotation of +100. What is the enantiomeric excess of R? ________ What is the percentage of R enantiomer in the sample? ________ Circle the statement(s) that is/are true? a) R and S enantiomers of a compound have identical melting points. b) Diastereomers have different chemical properties in a chiral solvent. c) R and S enantiomers of a compound react at identical rates with chiral reagents. d) All chiral centers are not stereocenters. Circle the statement(s) that is(are) true regarding racemic mixtures? a) 40% (1S,3R)-mandelic acid and 60% (1R,3S)-mandelic acid is not a racemic b) A racemic mixture is optically active. c) A racemic mixture has an optical rotation of zero. d) A racemic mixture has a 50% enantiomeric excess. Which of the following has the highest boiling point? a) 2,3-dimethylbutane b) 2-methylpentane c) 3-methylpentane d) hexane Briefly explain:___________________________________________________________ mixture.

16.

17.

18.

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19. Which of the following represents a different stereoisomer?
Br H 3C H3 CH 2C Br H 3C H Br Br H CH3 CH 2 CH 3

H 3C

H CH 2CH3

Br

20.

Consider the structures below. Answer the following questions using the terms enantiomers, diastereomers, or the same compound.
COOH Cl C CH H OH COOH COOH H OH Cl COOH C CH CHO HO H F CH CH 2 CHO CH CH 2 F H CHO OH CHO

Compounds 1 and 2 are ____________________________________. Compounds 3 and 4 are ____________________________________. 21. Which of the following compound(s) rotate(s) plane polarized light? a) cis-1,2-dibromocyclohexane b) cis-1,3-dibromo-2-fluoro-5-methylcyclohexane c) cis-2,5-dibromo-1-fluoro-2-methylcyclohexane d) cis-1,4-dibromo-2-methylcyclohexane Circle and label each non-alkane functional group in the following compound? Use primary, secondary and tertiary descriptions, if appropriate.
O O HO O N H

22.

23.

Which of the following statements is not true? a) The sp3 C-H bond of an alkane is longer than the sp2 C-H bond of an alkene. b) The carbon-carbon double bond of an alkene is 2 times as strong as a carbon-carbon single bond in an alkane. c) The carbon-carbon double bond of an alkene is shorter than the carbon-carbon triple bond of an alkyne. d) The sp CH bond of an alkyne is weaker than the sp3 CH bond of an alkane. Draw the Newman projection for butane with a dihedral angle of 120 degrees. Your view is down carbons 2 and 3.

24.

Briefly describe the type(s) of strain experienced in this structure? __________________________________________________________________________________ __________________________________________________________________________________ 25. Who won the Superbowl? a) New Orleans Saints b) Dallas Cowboys