BUC Midterm exams Fall 2011 November 13th, 2011 November 20th 2011

MIDTERM EXAMINATIONS FALL 2011 EXAM DETAILS Course Name: Organic Chemistry Model Answer Instructor: Dr. Imtiaz Khalid Timings: 11:00 12:30 Total marks: 100 Course Code: CHM 102 Date: November 15th 2011 Location: Lecture F02 Number of exam pages: 9

BUC policy states that the midterm exam constitutes 20% of your final grade for the course. All rules and regulations have been provided to you in the student handbook and the exam instructions document. EXAM SPECIFIC INSTRUCTIONS 1. 2. 3. 4. Read each question carefully For multiple choice questions, make sure you circle one answer; questions with more than one answer will NOT be graded For questions with short answers, answer each question clearly and completely but keep your answers concise Attempt each question and use your time efficiently

Good Luck!

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Circle the best fit answer in all of the following questions. (2.5 pts each, 70 points total) 1. Which is the shortest of the carbon-carbon single bonds indicated by arrows in the following compounds? A)
H3 C CH3
C CH CH2

B)
H3C

C)
H3C

CH
C C CH CH

D) E)
HC C H2C HC

2. Which of the structures below is not expected to contribute to the CO2 resonance hybrid? A)
O C O

B)

C) O D) E) 3. A) B) C) D) E) 4. A) B) C) D) E)

O O

C C C
C

O O O
O

Which molecule has a zero dipole moment? CH3Cl CH2Cl2 CHCl3 CCl4 None of these Which of these is the weakest of the intermolecular attractive forces? Ion-ion van der Waals Dipole-dipole Covalent bonding Hydrogen bonding

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5. Which of the following is not found in the following substance? CH3CH2CH2CH2CH2OH A) Ion-ion B) van der Waals C) Dipole-dipole D) Resonance E) Hydrogen bonding 6. Consider the following: CH3CH2CH2CH=CHCH2CH2CH3 I CH3CH2CH=CHCH2CH2CH2CH3 III A) B) C) D) E) CH3CH2CH2CH2CH2CH2CH=CH2 II CH2=CHCH2CH2CH2CH2CH2CH3 IV

Which structures can exist as cis-trAns: isomers? I and II I and III I and IV II and III I alone

7. Consider the equilibrium PO43

+ H2O

P 42

Which are the Bronsted-Lowry bases? A) PO43 and HPO42 B) PO43 and OH C) PO43 and H2O D) H2O and OH E) H2O and HPO42 8. Which functional groups are present in the following compound?

A) B) C) D) E)

Alkene, 1 alcohol, ketone Alkene, 2 alcohol, aldehyde Alkene, 2 alcohol, ketone Alkyne, 1 alcohol, aldehyde Alkyne, 2 alcohol, ketone

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9. Which of the following represent pairs of constitutional isomers? OH O A)

O

and
CH3

O
H H Br

B)
H

CH3 Br H CH2 Br CH3

and Br

C)

and

H CH3

D) More than one of these pairs E) All of these pairs 10. A) B) C) Of the following compounds, the one with the highest boiling point is: CH3CH3 CH3CH2Cl CH3C=O

H D) CH3CH2OH E) CH3CH2OCH2CH3

11. For a molecule to possess a dipole moment, the following condition is necessary but not sufficient. A) Three or more atoms in the molecule B) Presence of one or more polar bonds C) A non-linear structure D) Presence of oxygen or fluorine E) Absence of a carbon-carbon double or triple bond 12. Which compound listed below is a secondary alcohol? A) CH3CHCH2CH3
OH B) CH3CHCH2OH

C)

CH3 CH3 CH3COH

CH3 D) CH3CH2CH2CH2OH E) CH3CH2CH2OCH3

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13.

The compound shown below is a substance called Capsaicin, found in varying concentrations in several varieties of hot peppers, and responsible for their respective degrees of heat. Which functional groups are present in the molecule of capsaicin?
O N H O OH

A) B) C) D) E)

Capsaicin Alkene, ketone, amine, alcohol, ester Alkene, ketone, alcohol, ether Alkene, amine, phenol, ether Ether, alcohol, alkene, amide Ester, phenol, alkene, amide

14.

Which compound(s) contain(s) tertiary carbon atom(s)?

F

I
Br

II

III
OH OH

A) B) C) D) E)

I, II, III I II, III I, IV V

IV

15. A) B) C) D) E)

The hybridization state of the charged carbon in a carbocation is sp4 sp3 sp2 sp s

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16. Which compound has an index of hydrogen deficiency equal to three?

II

III

IV A) B) C) D) E) I, III IV, V V II II, V

17. Which of the following statements is true when ethane, ethene and acetylene are compared with one another? A) Acetylene is the weakest acid and has the longest C-H bond length. B) Acetylene is the strongest acid and has the shortest C-H bond length. C) Ethane is the strongest acid and has the longest C-H bond length. D) Ethene is the strongest acid and has the shortest C-H bond length. E) Ethene is the weakest acid and has the longest C-H bond length. 18. A) B) C) D) E) Which of these is not a Lewis acid? AlCl3 H3O+ FeCl3 SO3 C4H10

19. When proton transfer reactions reach equilibrium, there have been formed: A) the weaker acid and the weaker base. B) the weaker acid and the stronger base. C) the stronger acid and the weaker base. D) the stronger acid and the stronger base. E) All proton transfers go to completion; they are not equilibrium processes.

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20. Which type of compound will not show evidence of hydrogen bonding? A) B) C) D) E) Aldehyde Alcohol Carboxylic acid Phenol Primary amine

21. The following substance is expected to have low solubility in which of the following solvent(s)?
O Na O

A) B) C) D) E)

CCl4 C2H5OH CHCl3 CH2OHCH2CH2CH2CH2CH2OH The given substance is likely to be quite soluble in all of the solvents described

22. Which of the acids below would have the strongest conjugate base? A) CH3CH2OH pKa = 18 B) CH3CO2H pKa = 4.75 C) ClCH2CO2H pKa = 2.81 D) Cl2CHCO2H pKa = 1.29 E) Cl3CCO2H pKa = 0.66 23. Which one of the following is a true statement? A) The stronger the acid, the larger is its pKa. B) The conjugate base of a strong acid is a strong base. C) Acid-base reactions always favor the formation of the stronger acid and the stronger base. D) Strong acids can have negative pKa values. E) Hydrogen need not be present in the molecular formula of a Bronsted-Lowry acid. 24. As a consequence of the "leveling effect," the strongest acid which can exist in appreciable concentration in aqueous solution is: A) H3O+ B) H2SO4 C) HClO4 D) HCl E) HNO3

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25.

A correct IUPAC name for the following compound is:

OH

Cl

A) B) C) D) E) 26.

4-propyl-5-chloro-3-heptanol 4-propyl-3-chloro-5-heptanol 4-(1-chloropropyl)-3-heptanol 5-chloro-4-propyl-3-heptanol 3-hydroxy-4-propyl-5-chloroheptane

A correct IUPAC name for the following compound is:

Br

A) B) C) D) E) 27.

3,6,7-trimethyl-4-bromo-1-octene 4-bromo-3-methyl-6-isopropyl-1-heptene 4-bromo-3,6,7-trimethyl-1-octene 4-bromo-6-isopropyl-3-methyl-1-heptene 4-bromo-6-isopropyl-3,6-dimethyl-1-hexene

The IUPAC name for is:

A) B) C) D) E)

6-Ethyl-3,4-dimethylheptane 2-Ethyl-4,5-dimethylheptane 3,4,6-Trimethyloctane 3,5,6-Trimethyloctane 2-(1-Methylpropyl)-4-methylhexane

28. The correct sequence of the ions shown, in order of increasing basicity, is: A) CH3CH2: < CH2=CH: < HC C: B) CH3CH2: < HC C: < CH2=CH: C) HC C: < CH3CH2: < CH2=CH: D) CH2=CH: < HC C: < CH3CH2: E) HC C: < CH2=CH: < CH3CH2:

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II.

Answer each of the following. (20 points) 1. Draw three isomers of C3H8O and classify each according to functional group. (6 pts) Ans: C3H8O
OH OH O

primary alcohol

secondary alcohol

ether

2. Carbon dioxide is non- polar, despite the fact that oxygen is much more electronegative than carbon. Briefly explain why, using relevant diagrams as appropriate to illustrate your answer. (5 pts) Ans: The overall dipole moment of a polyatomic molecule depends on two factors: the polarity of various bonds and molecular geometry, since dipole forces have both magnitude and direction. In some molecules containing bonds of identical polarity, the molecular geometry may result in a net cancellation of the overall dipole forces. This is what happens in carbon dioxide: although there are two polar C-O bonds, because of the linear geometry of the molecule, the net dipole is zero. .. .. : O C O:

3. Ethanol, C2H5OH, and propane, C3H8, have approximately the same molar mass, yet, ethanol has a much higher boiling point. Briefly explain why. (3 pts) Ans: Strong hydrogen bonding between molecules of ethanol leads to elevation in boiling point. No hydrogen bonding is possible between molecules of propane, resulting in a lower boiling point compared with ethanol.

4. Draw three tertiary amine isomers of C6H15N ( 6 pts) Ans:

N N N

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III.

Fill in the blanks. (10 points) 1. Addition reactions are characteristic of compounds with ______________. Ans: multiple bonds 2. Heterolytic bond-breaking produces __________. Ans: charged fragments/ions 3. The process of bond-breaking where each fragment takes away one of the electrons from the bond is called ____________. Ans: homolysis 4. According to Lewis theory, a base is a substance that can _________. Ans: donate a lone pair of electrons 5. Reagents that seek to react with a proton or some other electron-deficient center are called ____________. Ans: nucleophiles 6. According to Bronsted-Lowry theory, an acid is a substance that can ____________. Ans: donate a proton 7. The four basic types of reactions are: ________________, ________________,______________________and_____________________. Ans: substitution, addition, elimination, rearrangement 8. Organic compounds are classified into chemical families on the basis of similarities in chemical properties; these similarities are primarily due to the presence of characteristic arrangements of atoms known as ________________. Ans: functional groups 9. A group in which a carbon atom has a double bond to an oxygen atom is called a __________. Ans: carbonyl

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