Study Union Final Exam Review Fall 2017

Monday 12/4, 12:00 – 2:00 pm, Cape Florida

Organic Chemistry II (CHM2211)

SI Leader: Ajay G.

I. Nomenclature Nomenclature of Carboxylic Acid Derivatives

Base name (IUPAC) Base Name (common)

Example Compound

IUPAC Name Common Name

Alkane alkane - CH3CH3 Ethane -

Carboxylic acid Alkane Alkanoic acid

Alkane Alkanic acid

CH3COOH Ethanoic acid Acetic acid

Acid halide Alkanoic acid Alkanic acid

Acid anhydride Alkanoic acid Alkanic acid

Ester Alkanoic acid Alkanic acid

Amide Alkanoic acid Alkanic acid

Nitrile Alkanoic acid Alkanic acid

Number of Carbons IUPAC Common name1 Meth- Form-2 Eth- Acet-3 Prop- Propion- 4 But- Butyr- 5 Pent- Valer-

Suffixes for Common Functional Groups: Alkenes: ___________ Alkynes:_____________

Alcohols:___________ Amines: _____________

Aldehydes: _________ Ketones: ____________

Ethers (two ways): _________________________________________

Steps for naming a compound (loose guideline) 1. Identify parent chain 2. Identify and name substituents3. Number parent chain4. Arrange substituents alphabetically5. Indicate any stereochemistry

Practice Problems

1. What is the proper name for this compound?a. 5-bromo-2-nitrophenylb. 3-bromo-6-nitrophenolc. m-bromo-o-nitrophenold. 5-bromo-2-nitrophenol

2. What is the IUPAC name for this compound? a. N-(4-chlorophenyl)ethanamideb. P-chlorobenzylethanamidec. 4-chlorobenzamide d. N-(4-chlorobenzyl)ethanamide

3. Name the following compound:

4. Which of these molecules contains amide, ketone, ester, and ether functional groups?

a.

b.

c.

d.

II. Structure, Hybridization, Resonance, and Aromaticity

Constitutional isomers have the same molecular formula but different connectivity

of atoms and _______________ (identical/different) physical properties

Hybridization is determined by the number of _______ (π/σ/σ+π) bonds and

number of _________________

An atom that is sp3 hybridized has ____________________ electronic geometry

An atom that is sp2 hybridized has ____________________ electronic geometry

An atom that is sp hybridized has _____________________ electronic geometry

Aromatic compounds contain a planar ring with _____________________________

p orbitals and ______________ number of pi electrons

Practice Problems

5. Draw the Newman projection that represents the most stable conformation of (CH3)2CHCH(CH3)2

6. Identify the lowest energy Lewis structure for nitrogen oxide (formal charges not shown)a. c.

b. d.

7. Which of the following structures have eight π electrons?

I. II. III.

a. I onlyb. II onlyc. III onlyd. I, II, and III

8. Which of these structures is/are aromatic?

I. II. III. IV.

a. I onlyb. I and II c. II and IIId. I, II, and III e. All of the above

9. In which of these Lewis structures would sulfur be assigned a formal charge of +2?

a. b. c. d.

10. For which carbocation can the most resonance forms be written to show the delocalization of the positive charge?

a. b. c. d.

11. What is the hybridization of the carbon atom in the following carbene?

a. sp3

b. sp2

c. spd. s

12. Which compound absorbs at the shortest wavelength (highest energy) in the UV spectrum? a. c.

b. d.

III. Acids and Bases A Bronsted-Lowry acid is a proton ______________, while a Bronsted-Lowry base is

a proton ________________

A Lewis acid is an electron ________________, while a Lewis base is an electron

_________________

Relative acidity can be analyzed by comparison of ___________________________.

The stronger acid will have a ____________ (more/less) stable conjugate base.

The four factors to consider when comparing the stability of conjugate bases are:

__________________________________________________________________

Practice Problems

13. Which of the following is the weakest base? a. c.

b. d.

14. Rank the following in order of decreasing acidity (most acidic to least)

I. CH3OH II. CH3OH2+ III. CH3NH2 IV. CH3NH3

+

a. III > I > IV > IIb. II > IV > I > III c. III > IV > I > II d. II > I > IV > III

15. Rank the following in order of increasing acidity

I. II. III. IV.

a. I < II< IV < III b. III < I < IV < II c. I < IV < III < II d. I < III < II < IV

16. Which sets of hydrogen atoms in the compound below will undergo deuterium exchange with CH3CH2OD in the presence of CH3CH2ONa?

IV. III. II. I.

a. II and III onlyb. I, II, and III c. II, III, and IV, only d. I and IV only

17. Rank the following compounds in order of increasing acidity (least acidic to most acidic)

I. II. III. IV.

IV. Stereoisomerism _____________ isomers have the same connectivity of atoms and but different

arrangement in 3D space

Enantiomers are ______________________________________________________

and have _________________ (identical/different) physical properties and differ in

the way they __________________________________________________

Diastereomers are ____________________________________________________

When is a compound chiral?

___________________________________________________________________

Practice Problems

18. Which of the following has “S” configuration? a. c.

b. d.

19. What is the correct stereochemical description of the relationship between this pair of molecules?

a. Enantiomersb. Diasteriomersc. Identicald. Constitutional isomers

20. Which of the following is/are optically active?

I. II. III.

a. I onlyb. II onlyc. III onlyd. I and III onlye. I, II, and III

V. Substitution and Elimination Reactions Practice Problems

21. Which mechanism best represents the E2 reaction between 1-bromopropane and KOH?a. c.

b. d.

22. Draw all possible products of dehydrohalogenation of the following compound with potassium hydroxide:

23. Predict the major product when the following compoundis treated with hydrobromic acid:

a. c.

b. d.

24. Which substrate is most reactive towards solvolysis? a. c.

b. d .

25. Which of the following is most reactive towards nucleophilic acyl substitution? a. N-methylethanamideb. Ethanoic acid c. Ethanoic anhydrided. Sodium ethanoatee. Ethanoyl bromide

VI. Reactions and Synthesis Practice Problems

26. What type of reaction converts FAD to FADH2?

FAD FADH 2

a. Dihydrogenation b. Electrophilic aromatic substitution c. Oxidation d. Reduction

27. Which reagent will accomplish the following transformation?

a. CH3CH2Lib. CH3CH2CuLic. CH3CH2MgBrd. (CH3CH2)2CuLi

28. Draw the major product formed when benzene is reacted with 1-chlorobutane and aluminum trichloride

29. Which set of reagents would most likely convert toluene to the following compound:

a. Br2 with UV lightb. ClCH3 with AlCl3

c. Br2 with FeBr3

d. Br2 in CCl4

30. Draw the polymer produced from the following monomer: (CH3)2C=CH2

31. predict the products when the compound below is heated in a solution sodium hydroxide and

water.

O

32. Which of the following is the product of an aldol condensation? a. c.

b. d.

33. Draw the product formed when benzaldehyde and acetophenone are reacted in a solution of sodium hydroxide and water.

34. Which of the following is a key intermediate in the reaction below?

A. B. C. D.

35. Which of the following methods will produce 1-pentanol?

I.

II.

III.

IV.

A. I onlyB. II and IIIC. I and IV D. I, II, and IIIE. All of the above

36. Which of the following methods will produce cyclopentanol?

A. C.

B. D.

37. Which of the following dienes cannot participate in a Diels-Alder reaction? a. c.

b. d.

38. Predict the product when the following compound is treated with excess chromic acid:

a. c.

b. d.

39. Which of the following compounds is a product of the Dieckmann cyclization shown below?

a. . c.

b. . d.

40. Show the starting materials that can be used to prepare the following compound by a Diels-Alder reaction.

a.

b.

c.

d.

41. Predict the product of the following reaction:

a. c.

b. d.

42. Predict the product of the following reaction: .

43. Predict the product when ethylene glycol reacts with acetaldehyde under dry conditions (removal of water) a. c.

b. d.

44. Predict the product of the following reaction:

a. c.

b. d.

45. Predict the product of the following reaction:

46. Predict the product of the following reaction

a. c.

b. d.

VII. Spectroscopy

Infrared Spectroscopy

(smaller / larger) atoms give bonds that vibrate at (higher / lower) frequencies, thereby corresponding to a higher wavenumber.

(stronger / weaker) bonds will vibrate at higher frequencies, thereby giving rise to a (higher / lower) wavenumber.

Identify the regions in which the following absorption peaks appear: Triple bonds, double bonds, single bonds, and bonds to hydrogen.

Conjugated π bonds absorb at a (higher / lower) wavenumber than localized π bonds. Explain.

The intensity of a signal corresponds to the ___________________ of a bond. The broad signals associated with alcohols and carboxylic acids are due to

__________________________________________ Explain.

Mass Spectrometry

Fragmentation of the molecular ion generates a ______________ and a ________________ The mass spectrometer detects the ___________________ fragment The molecular ion peak corresponds to the _________________________ of the compound The base peak is the ____________ peak in the spectrum and corresponds to the (most / least)

abundant, or (most / least) stable, fragment. The base peak is (always / sometimes / never) the same as the molecular ion peak.

NMR Spectroscopy

If the replacement test yields the same compound, then the two hydrogen atoms are said to be ____________________ and (are / are not) chemically equivalent.

If the replacement test yields enantiomers, then the two hydrogen atoms are said to be ____________________ and (are / are not) chemically equivalent.

If the replacement test yields diastereomers, then the two hydrogen atoms are said to be ____________________and (are / are not) chemically equivalent.

The (right / left) side of an NMR spectra is described as downfield, and the (right / left) side of the spectra is described as upfield.

The more desheilded a proton is, the farther (upfield / downfield) it will appear in an HNMR spectra.

Practice Problems

47. Which compound would you expect to show a (M-18) peak in its mass spectrum?A. 2-methylbutane B. 1-butanol C. butanamine D. diethyl ether

48. Which of the following compounds would yield a molecular ion peak with an odd number m/z value? a. C9H15Fb. C7H10N2Oc. C8H10NId. All of the above

49. How many signal would you expect to see in the HNMR spectrum of (S) 2-bromopentane?A. 5B. 6C. 7D. 8E. None of the above

50. Which, if any, of the following will display spin-spin splitting in HNMR? a. (CH3)3COCH3

b. Br(CH2)3Brc. Para-xylene, CH3C6H4CH3

d. None of the above

51. Which of the following compounds would have a base peak at m/z=43? a. CH3CH2CH2CH2CH2CH3

b. (CH3CH2)2CHCH3

c. (CH3)3CCH2CH3

d. (CH3)2CHCH(CH3)2

52. The hydrogens shown areA. HomotopicB. Enantiotopic C. DiastereotopicD. Stereotopic

53. The hydrogens shown areA. Homotopic B. DiastereotopicC. Enantiotopic D. None of the above

54. A compound shows strong infrared absorption at 1100 cm-1, but none from 3300 to 3400 cm-1. Its 1H NMR spectrum has sharp singlet peaks at δ 1.3 and 4.0 ppm (intensity 3:2). Its proton decouples 13C NMR spectrum shows three peaks at δ20, 68, and 98 ppm. What is the structure of the compound?

a. b. c. d.