Organic Chemistry Questions
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1 Organic Chemistry Questions The Covalent Bond 1. The hybridization of the central carbon in CH 3 C N and the bond angle CCN are sp 2, 180. sp, 180. sp 2, 120. sp 3, Which of the following statements about an sp hybridized carbon is FALSE? It is divalent. It forms bonds that are linear. It has two p orbitals. It always forms triple bonds to carbon. 3. Which molecule has the largest dipole moment? HCl CCl 4 H 2 S CO 2 4. What are the hybridizations of carbons 1 and 2 respectively in the following structure? sp 3 and sp 2 sp 2 and sp 3 sp 3 and sp sp 2 and sp 2
2 5. What are the hybridizations of atoms 1 and 2 respectively in the following structure? sp 3 and sp 2 sp 2 and sp 3 sp 3 and sp sp 2 and sp 2 6. Identify the orbital hybridization at the two indicated carbons in the molecule below. C 1 : sp; C 2 : sp C 1 : sp 2 ; C 2 : sp 2 C 1 : sp; C 2 : sp 2 C 1 : sp 2 ; C 2 : sp 7. How many total resonance structures can be drawn for the following anion (include those without separation of charge)?
3 8. How many resonance structures can be drawn for the following molecule? The correct geometry around oxygen in CH 3 OCH 3 is linear. bent. tetrahedral. trigonal planar 10. Determine the relationship between the two molecules shown. constitutional isomers enantiomers diastereomers identical molecules 11. What is the correct name for this molecule? (2R,3R)-2-bromo-3-chlorobutane (2S,3R)-2-bromo-3-chlorobutane (2S,3S)-2-bromo-3-chlorobutane (2R,3S)-2-bromo-3-chlorobutane
4 12. What is the specific rotation 20[α ] D of the following molecule? o o o 44.2 o 13. Which of the following physical properties differ for each of a pair of enantiomers? solubility in ethanol direction of rotation of plane-polarized light boiling point and melting point index of refraction 14. Determine the double bond stereochemistry (E or Z) for the following molecules. A: E; B: E A: Z; B: Z A: E; B: Z A: Z; B: E
5 15. Determine the double bond stereochemistry (E or Z) for the following molecules. A: E; B: E A: Z; B: Z A: E; B: Z A: Z; B: E Molecular Structure and Spectra 1. A strong signal at 1700 cm 1 in an IR spectrum indicates the presence of a(n) alcohol ether carbonyl amine 2. A strong signal at 3400 cm 1 in an IR spectrum indicates the presence of a(n) alcohol ether carbonyl amine
6 3. Deduce the structure of an unknown compound with molecular formula C 5 H 12 O using information given by its infrared spectrum. Intensity (peak): Frequency (cm 1 ): m 3300 m 2900 m 2800 m 1465 m 1450 m 1375
7 4. Deduce the structure of an unknown compound with molecular formula C 9 H 10 O using information given by its infrared spectrum. Intensity (peak): Frequency (cm 1 ): s 3100 m 2900 m 2800 s 1710 m-w 1600 m-w 1475 m 1465 m 1450 m 1375
8 5. Deduce the structure of an unknown compound with molecular formula C 5 H 8 O using information given by its infrared spectrum. Intensity (peak): Frequency (cm 1 ): m 3100 m 2800 s 1705 m-w 1640 m 1450 m Which of the following compounds a d has an IR absorption at 3300 cm 1? a b c d
9 7. When an external magnetic field is applied, what happens to the protons in a sample? All protons align with the fiel All protons align opposite to the fiel Some protons align with the field and some align opposite to it. All protons assume a random orientation 8. Which of the following compounds has the MOST deshielded protons? CH 3 Cl CH 3 I CH 3 Br CH 4 9. Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens (largest δ value first, smallest value last). CH 3 CH 2 CH 3 CH 3 OCH 2 CH 3 Cl 2 CHCH 2 CH 3 ClCH 2 CH 2 CH 3 a b c d b > c > a > d b > c > d > a c > b > a > d c > b > d > a 10. An unknown molecule A has 4 signals in the 1 H NMR spectrum. Which of the following corresponds to molecule A?
10 11. Deduce the structure of an unknown compound using the following 1 H NMR spectrum, mass spectroscopy data, and IR spectrum. 1 H NMR spectrum: δ1.30 (triplet, 6H) δ4.29 (quartet, 4H) δ (multiplet, 4H) Mass Spectrum: m/e: Intensity: (as % of base peak) % % % IR Spectrum: Intensity (peak): Frequency (cm 1 ): s 3100 m 2900 m 2800 s 1740 m-w 1600 m-w 1475 m 1465 m 1450 m 1375 s
11 12. A compound of formula C 5 H 12 gives 1 signal in the 1 H NMR and 2 signals in the 13 C NMR. The compound is pentane. 2-methylbutane. 2,2-dimethylpropane. Cannot tell without more information. 13. How many methyl peaks would you expect to observe in the 1 H NMR spectrum of cis-1,4-dimethylcyclohexane?
12 14. An unknown compound A has the molecular formula C 4 H 8 O 2. Based on the following 1 H NMR spectrum, what is the structure of compound A?
13 15. The 1 H NMR spectrum of a compound is shown below. What is the structure of the compound?
14 16. How many absorption bands will appear in the 13 C NMR spectrum for the following compound? How many absorption bands will appear in the 13 C NMR spectrum for the following compound? Not only the molecular ion peak, but all peaks in the mass spectrum of chlorobenzene are accompanied by a smaller peak one mass unit higher. This peak is due to which of the following? capture of an H atom presence of a 13 C presence of a 36 Cl capture of a proton 19. What is the exact mass (in atomic mass units: C, ; H, ; N, ; O, ) of the molecular ion of a compound with molecular formula C 3 H 8 O?
15 Separations and Purifications 1. Which of the following may be separated by ordinary physical methods? a pair of identical molecules a pair of enantiomers a pair of diastereomers a pair of identical atoms 2. Which of the following may be separated by ordinary physical methods? (R)-3-bromo-1-butene and (S)-3-bromo-1-butene cis-2-bromo-2-butene and trans-2-bromo-2-butene (2R,3S)-1,2-dibromobutane and (2S,3R)-1,2-dibromobutane (R)-2-bromobutane and (S)-2-bromobutane Hydrocarbons 1. Place the following structures properly on the (abbreviated) energy surface for cyclohexane ring reversal. 1 = b or c, 2 = a, 3 = d, 4 = b or c 1 = d, 2 = b or c, 3 = d, 4 = a 1 = d, 2 = b or c, 3 = a 1 = b or c, 2 = d 3 = a, 4 = b or c
16 2. Which of the following cyclohexane conformations has the MOST energy (is the LEAST stable)? chair half-chair boat twist-boat 3. Which of the following molecules is trans-1, 2-dimethylcyclohexane? 4. What is the IUPAC name of the following molecule? 1,2-dimethylhexane 2,4-dimethylcyclohexane Dimethylcyclohexane 1,3-dimethylcyclohexane
17 5. Which compound has the highest melting point? decane 2,2,3,3-tetramethylbutane 2,2,3-trimethylpentane 4-methylnonane 6. Which of the following alkanes will have the lowest boiling point? 7. Which of the following cycloalkanes has the MOST strain energy? cyclobutane cyclopentane cyclohexane cycloheptane 8. The balanced equation for the combustion of pentane is 4 C 5 H O 2 20 CH H 2 O 2 C 3 H 8 + O 2? CH H 2 O C 5 H O 2 5 CO H 2 O C 3 H O 2 3 CO H 2 O
18 9. Which of the following is the most stable radical?
19 10. What is the major product of the following reaction?
20 11. What is the major product of the following reaction? 12. Which of the following occurs during the initiation stage of a radical mechanism? Nonradicals are formed from radicals. Radicals are formed from other radicals. Radicals are formed from nonradicals. Nonradicals are formed from other nonradicals.
21 13. What is the product of the following reaction? 14. Which version of the radical halogenation of an alkane is MOST selective? fluorination chlorination bromination iodination Oxygen-containing Compounds 1. Which of the following will NOT convert 1-butanol into 1-chlorobutane in one step? SOCl 2 PCl 3 HCl CCl 4
22 2. Give the major product of the following reaction. 3. The Williamson ether synthesis produces ethers by reacting an alcohol with a metal. alkoxide with a metal. alkoxide with an alkyl halide. alkyl halide with an aldehyde. 4. Ozonolysis (O 3 in CH 2 Cl 2 ) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H 2 /Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? 2,7-Dimethyl-2,8-nonadiene 2,7-Dimethyl-1,8-nonadiene 2,7-Dimethyl-1,6-nonadiene 2,7-Dimethyl-1,7-nonadiene 5. Predict the major product of the following reaction. m-chlorophenol o-chlorophenol and p-chlorophenol o-hydroxytoluene and p-hydroxytoluene m-hydroxytoluene
23 6. Which of the following compounds does NOT give a tertiary alcohol upon reaction with methylmagnesium bromide? 3-methylpentanal ethyl benzoate 4,4-dimethylcyclohexanone 4-heptanone 7. Which of the following compounds gives a secondary alcohol upon reaction with methylmagnesium bromide? Assume the usual acid workup. butyl formate 3-pentanone pentanal methyl butanoate 8. Predict the product of the following reaction. (1R,2S)-2,3,3-trimethylcyclohexanol + enantiomer (R)-1,2,2-trimethylcyclohexanol + enantiomer (1S,2S)-2,3,3-trimethylcyclohexanol + enantiomer (1R,2S)-2,3,3-trimethylcyclohexanediol + enantiomer 9. Which of the following statements about organometallic compounds is FALSE? Alkyllithium reagents (RLi) add to the carbonyl group of aldehydes and ketones. Grignard reagents (RMgBr) add to the carbonyl group of aldehydes and ketones. Alkyllithium and Grignard reagents do not add to esters. Grignard reagents are prepared in ether or tetrahydrofuran (THF).
24 10. What is the name of the following compound? Ethyl cyclohexyl ether Hexyl propyl ether 1-Ethoxycyclohexane Cyclohexyl propyl ether 11. What is the major product formed in the following synthesis?
25 12. Which is the correct IUPAC name for the following compound? 4-Isopropyl-1,1-dimethyl-1-pentanol 5-Isopropyl-1,1-dimethyl-2-hexanol 1,1,4,5-Tetramethyl-1-hexanol 2,5,6-Trimethyl-2-heptanol 13. What is the correct name of the following compound? 3-methylbenzoic acid m-methylbenzoate tolylcarboxylate methylbenzoate 14. What is the correct name of the following molecule? 3-hexene-1-one 5-cyclohexan-1-one 4-cycloheptenone 3-cyclohexen-1-one
26 15. Predict which of the following compounds will have a lower boiling point than 1- butanal. 1-butanol 2-butanol 1-butene butanoic acid 16. Predict the product of the following reaction. PhCH 2 OH + PCC (pyridinium chlorochromate) in methylene chloride benzophenone benzoic acid benzaldehyde benzyl chloride 17. What is a proper name for the following ester? 2-butyl ethylester ethyl 2-pentanoate ethyl 2-methylbutanoate methylbutanoic ethyl ester 18. The correct IUPAC name for ester B is phenylmethyl-2,4,4-trimethylpentanoate benzyl 2-methyl-4,4-dimethylpentanoate benzyl 2,4,4-trimethylpentanoate benzyl 2,4,4-trimethylbutanoate.
27 19. What is the acid anhydride that is hydrolyzed?
28 20. What is the product of the following reaction?
29 21. What are the two possible tautomers for the following ketone?
30 22. Which of the following compounds is the product of an aldol condensation reaction? Amines 1. What is the sequence of reagents that will accomplish the synthesis of the following aromatic amine from benzene? CH 3 Cl, AlCl 3 ; HNO 3, H 2 SO 4 ; H 2 CH 3 Cl, AlCl 3 ; HNO 3, H 2 SO 4 ; Fe, HCl; NaOH HNO 3, H 2 SO 4 ; Fe, HCl; NaOH; CH 3 Cl, AlCl 3 HNO 3, H 2 SO 4 ; CH 3 Cl, AlCl 3 ; Fe, HCl; NaOH
31 2. Which of the following aniline derivatives is the strongest base?
32 3. What is the product of the following reaction?
33 4. What is the name of the following compound? ethylmethylisopropylamine ethylpropylsec-butylamine ethylmethylpropylamine sec-butylethylpropylamin 5. Which of the following amines is a tertiary amine?
34 6. What is the product of the following synthesis? 7. Supply the correct words to complete this sentence: Electron-withdrawing groups such as nitro the basicity of anilines, especially when substituted. increase ; ortho or para increase ; meta decrease ; ortho or para decrease ; meta
35 Biological Molecules 1. Which of the following amines is pyridine? 2. Which of the following statements is NOT true regarding fatty acids? Fatty acids dissolve in nonpolar solvents. Triglycerides are esters of fatty acids. Most naturally occurring fatty acids have trans double bonds. Fatty acids are biosynthesized from acetate. 3. Which of the following statements regarding the biosynthesis of cholesterol is FALSE? Cholesterol has the same carbon skeleton as its biosynthetic precursor, lanosterol. Cholesterol is derived from the dimerization of farnesyl pyrophosphate in a headto-head manner. Cyclization of squalene to cholesterol is initiated by acid-catalyzed ring opening of an epoxide. Cholesterol has three fewer carbon atoms than lanosterol.
36 4. Which of the following represents the structure of a triacylglyceride?
37 5. Which of the following compounds does NOT undergo mutarotation? glucose sucrose ribose fructose 6. Which statements are correct about the following disaccharide? Ring A is an acetal in the α configuration; ring B is a hemiacetal in the ß configuration. Ring A is an acetal in the ß configuration; ring B is a hemiacetal in the α configuration. Ring A is a hemiacetal in the α configuration; ring B is an acetal in the ß configuration. Ring A is a hemiacetal in the ß configuration; ring B is an acetal in the α configuration.
38 7. A glycoside is the carbohydrate form of an ether. acetal. aglycone. alcohol. 8. Which of the following amino acids is achiral? alanine glycine serine cysteine 9. Which of the following is NOT a part of the primary protein structure? the amino acid sequence the disulfide linkages the planar nature of the amide linkage the conformation of the polypeptide backbone 10. Which of the following statements about the conformation (secondary and tertiary structure) of proteins is FALSE? The four atoms of an amide linkage ( CO NH ) lie in a plane as a result of resonance between the nitrogen and the carbonyl group. Electrostatic attraction occurs between basic and acidic side chains. The favored conformation of a protein is always that which has the greatest number of hydrogen bonds. The presence of the amino acid proline has the effect of turning a corner in a protein. 11. Which of the following statements about an enzyme is FALSE? An enzyme is usually a large protein. An enzyme is a catalyst for biological reactions. An enzyme is a chiral molecule. An enzyme changes the equilibrium constant of a reaction. 12. Which of the following statements about the arrangement of a protein in three dimensions is FALSE? As a result of hydrogen bonding, a portion of a protein may exist as a righthanded α-helix with 3.6 amino acid residues per turn, and a repeat unit of 5.4 Å. As a result of hydrogen bonding a portion of a protein may exist as a pleated sheet, in which the repeat unit is 7.0 Å. In a pleated sheet, the polyamide chains may be parallel or antiparallel. A portion of a protein may exist as a flat sheet with a repeat unit of 7.2 Å.
39 13. Which of the following is NOT an example of secondary structure found in proteins? ß-pleated sheet α-helix hydrophobic folding random coil 14. Which descriptors fit the following sugar best? ketose, furanose, α ketose, furanose, ß aldose, pyranose, ß aldose, pyranose, a
40 15. Where are the isoprene subunits in the following terpene?
41 16. Which of the following tetracyclic compounds corresponds to the typical 17-carbon steroid nucleus?
42 17. Which of the following is a steroid?
43 Organic Chemistry Answers The Covalent Bond 1. (b) 2. (d) 3. (a) 4. (a) 5. (d) 6. (d) 7. (d) 8. (c) 9. (b) 10. (b) 11. (d) 12. (c) 13. (b) 14. (d) 15. (b) Molecular Structure and Spectra 1. (c) 2. (a) 3. (c) 4. (b) 5. (c) 6. (a)
44 7. (c) 8. (a) 9. (b) 10. (c) 11. (d) 12. (c) 13. (a) 14. (a) 15. (a) 16. (d) 17. (c) 18. (b) 19. (b) Separations and Purifications 1. (c) 2. (b) Hydrocarbons 1. (a) 2. (b) 3. (d) 4. (d) 5. (b) 6. (c) 7. (a)
45 8. (c) 9. (a) 10. (d) 11. (a) 12. (c) 13. (a) 14. (c) Oxygen-containing Compounds 1. (d) 2. (b) 3. (c) 4. (c) 5. (c) 6. (a) 7. (c) 8. (c) 9. (c) 10. (d) 11. (b) 12. (d) 13. (a) 14. (d) 15. (c) 16. (c) 17. (c)
46 18. (c) 19. (c) 20. (c) 21. (d) 22. (c) Amines 1. (b) 2. (b) 3. (c) 4. (a) 5. (c) 6. (c) 7. (c) Biological Molecules 1. (c) 2. (c) 3. (a) 4. (c) 5. (b) 6. (a) 7. (b) 8. (b) 9. (d) 10. (c)
47 11. (d) 12. (d) 13. (c) 14. (b) 15. (c) 16. (c) 17. (b)
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