CHEM 2324

SPRING 2012

EXAM 1

Instructions: 1) Problems in this part of the exam are reported on SCANTRON, NOT this exam sheet. 2) As announced in class, an additional component of the exam is on a separate sheet. You will work out that problem on that sheet and you will hand that part of the exam in with the SCANTRON. 3) Make sure you name and student ID are on the SCANTRON, and the written part of the exam before you hand them in. 4) Do NOT put SCANTRON answers on the written (problem 17) constitutional isomer part of the exam 5) You may use the exam sheets as scratch paper. 6) You can keep the exam sheets including the structure and IR spectra sheets. A copy of the exam will be posted, with answers after grading is complete. However, MAKE SURE YOU TURN IN PROBLEM 17. 7) Structures for all problems are on the pages of this exam following questions 116. No further structural clarification will be made on any structures. A variety of structural renderings have been chosen to test your ability to interpret them. 8) Lone pairs may have been left off structures, but as discussed in class, are still present based on the overall charges shown for the atoms or molecules. However, for question 3, structures C, D, E, F, G have been explicitly shown with or without lone pairs so you can calculate charge. 9) The exam ends at 10:20AM. If I leave the room without your exam in my hands, it is considered a zero, and will be your dropped grade. 10) Problem valuation: a. The 16 problems on the SCANTRON part of the exam are worth 88% of your grade. No partial credit exists for the SCANTRON part of your grade. b. The written problem on the separate sheet which you also must hand in is worth 12% of your grade. Partial credit may be possible on this part of the exam. START OF EXAM: 1 For structure A, the correct number of hybridized atoms of each kind are: a. FOUR sp, TWO sp2, TWO sp3 b. TWO sp, TWO sp2, FOUR sp3 c. TWO sp, FOUR sp2, TWO sp3 d. TWO sp, THREE sp2, THREE sp3 e. None of the above 2 For structure B, how would you describe the geometry of carbon atoms 1, 2, 3, 4? All must be true within answer. a. 2 & 4 are linear, 1 is tetrahedral, 3 is trigonal planar b. 3 & 4 are linear, 1 is tetrahedral, 2 is trigonal planar c. 2 & 3 are trigonal planar, 1 is tetrahedral, 4 is linear d. 1 is tetrahedral, 2 & 4 is trigonal planar, 3 is linear e. None of the above

3 Of structures, C, D, E, F, G, which has a negative charge?. All parts of an answer must be true. See note (8) above in instructions. a. Structures D & F b. Structures C & F c. Structures E & F d. Structures C & E e. Structures C & D 4 Structure B has how many pi ( ) bonds? a. 0 b. 1 c. 2 d. 3 e. 4 5 Structure B has how many double and triple bonds? a. ONE double, TWO triple b. TWO double c. TWO triple d. TWO Double, ONE triple e. None of the above 6 Structure B has how many a. 5 b. 4 c. 3 d. 2 e. 1
sp2- sp3

bonds?

7 Which orbital gives the longest extension and the longest single bonds extending away from a carbon atom? Basically, which orbital on carbon would give the longest C-H bond length? a. sp b. sp2 c. sp3 d. 1S e. None of the above 8 Examine structures G, H, I, J, K, L, M, N, O Which is true? All assignments in an answer must be true. a. G is an alcohol, J is an alkyne, K is a nitrile b. M is an aldehyde, N is an ether, O is an ester c. N is an amide, O is a aldehyde, K is an ester d. K is an alkyne, M is an amine, J is a carboxylic acid e. None of the above

9 Of the constitutional isomers P, Q, R, S, T, which would be expected to have the lowest boiling point? a. Structure P b. Structure Q c. Structure R d. Structure S e. Structure T 10 Look at Structures U, V, W, X, Y. Which structures are resonance structures of each other? a. b. c. d. e. U and V V and Y W and X W and Y None of the above

11 For Structure Z, how many lone pairs should there be for a neutral structure? a. 2 b. 3 c. 4 d. 5 e. None of the above 12 Structure AA is: a. a primary alcohol b. a secondary alcohol c. a tertiary alcohol d. a quaternary alcohol e. none of the above 13 Structure BB is: a. a primary amine b. a secondary amine c. a tertiary amine d. a quaternary amine e. none of the above

14 Structure CC has (all parts of the statement must be true) a. ONE primary bromine & ONE secondary bromine b. ONE primary bromine & ONE tertiary bromine c. TWO secondary bromines d. ONE secondary bromine & ONE tertiary bromine e. None of the above 15 Consult the infrared spectrum that has been provided. This compound is: a. An alcohol b. A carboxylic acid c. A carbonyl compound (other than a carboxylic acid which also contains a C=O double bond d. A hydrocarbon (not a, b, c) e. None of the above 16 Consult the infrared spectrum that has been provided. Which is true a. DD is the alcohol O-H stretch b. DD is the C-H stretch c. DD is the C=O stretch d. DD is the carboxylic acid O-H stretch e. None of the above This completes the SCANTRON portion of the exam. On an additional page holding problem 17, please complete the question on that sheet. There is no SCANTRON answer for problem 17. You must turn in the sheet with problem 17 with your scantron. Do not forget your name.

H
B H3C
1

H H D

H
H C
3

C H C

O
H

H C
2

C
4

CH

H H C H E H
H

H C H F

H C H
H H C H3 C G O H H C CH3

H2C H2C HO CH2 CH2

CH3

O H3C J H C C H OH

N
H

CH3 C

H3C

C M

CH
H

C NH2 N

O O

Q
P

OH H3C N C CH3

OH H3C N H C CH2

O H3C N H C CH3

O H3C N C CH3

O H3C N H C CH3
OH

H3C

N
CH3

O H

AA

H3C

BB

Br

CC

Br

DD

1550 cm-1

PRINT NAME_________________

SID#______________________

Problem 17. There is no SCANTRON response for Problem 17. You must write the answer on this sheet. For the formula C4H9Cl, draw all possible constitutional isomers Make sure you show the Cl bonded to the molecule. Use the Dash bond structural rendering. Show all H atoms. Partial credit is possible on this problem. You must correctly draw all possible structures to get full credit. Wrong structures or duplicates will lose credit. Incorrectly drawn structures will lose credit. I will not tell you how many there are, but I will tell you it is much less than 10. You may use the reverse side if necessary. Dont forget name and SID#!!!!!
H H H C H H H H H H H H H H H Cl H H H H C C C Cl C H C C H H C Cl H C H H H H C C H C H H Cl

1-chlorobutane
H H C H C C H H H C

1-chloro-2-methylpropane
HH

2-chlorobutane

2-chloro-2-methylpropane