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69 Cards in this Set
- Front
- Back
How many signals are expected in a 13C NMR spectrum of methylcyclohexane? |
5 |
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The 1H NMR spectrum of a compound is shown below. What is the structure of the compound? |
this |
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Rank the following alkyl radicals in order of increasing stability (least < < most) |
1 < 3 < 4 < 2 |
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What is the major product of the following reaction? |
this |
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Consider the reaction of 2-methylpropane with a halogen. With which halogen will the product bealmost exclusively 2-halo-2-methylpropane? |
Br2 |
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Identify the reagent(s) that will promote the following transformation. |
B) HBr, peroxides |
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Which of the following statements regarding 1,2- or 1,4-conjugate addition of HBr to 1,3-butadiene isFALSE? A) The kinetic product, 3-bromo-1-butene, arises from the more stable carbocation intermediate. B) The thermodynamic product, 1-bromo-2-butene, is the more stable product. C) The kinetic product is favored by carrying out the reaction at high temperature. D) Formation of the two products arises from a common resonance stabilized carbocation intermediate. |
C) The kinetic product is favored by carrying out the reaction at high temperature. |
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What is the major product of the following reaction? |
this |
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What are the reactants needed to accomplish the following reaction? |
this |
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Which of the following compounds are aromatic? |
a, b, and d |
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Which compounds give a 1H NMR spectrum with two signals in a ratio of 2:3? a. CH3CH2Cl; b. CH3CH2CH3; c. CH3CH2OCH2CH3; d. CH3OCH2CH2OCH3 |
a, c, d only |
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Rank the following compounds in the order of increasing λmax |
B |
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In comparing kinetic control to thermodynamic control for the reaction of butadiene and HCl, which ofthe following statements represents kinetic control? A. The intermediate is more stable and the product is more stable. B. The intermediate is less stable and the product is more stable. C. The intermediate is more stable and the product is less stable. D. The intermediate is less stable and the product is less stable. |
C. The intermediate is more stable and the product is less stable. |
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The best sequence to use to form propylbenzene from benzene is A. Friedel–Crafts alkylation using 1-chloropropane and aluminum trichloride. B. Friedel–Crafts acylation followed by reduction. C. Electrophilic addition of 1-chloropropane. D. Nucleophilic aromatic substitution using propyl Grignard. |
B. Friedel–Crafts acylation followed by reduction. |
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6. What is the electrophile in the electrophilic substitution reaction of benzene using HNO3 and H2SO4? A. SO3 B. NO3 C. NO2+ D. NO+ |
C. NO2 + |
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Predict the major product of the following reaction. |
m-nitrobenzaldehyde |
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Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution |
Y |
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Which of the following compounds is the most acidic? CH3COOH; H2SO4; CH3OH; HF |
H2SO4 |
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Which of the following compounds does NOT give benzoic acid when heated with alkaline potassiumpermanganate? A. tert-Butylbenzene B. Ethylbenzene C. Toluene D. Styrene |
A. tert-Butylbenzene |
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Which of the following statements about organometallic compounds is FALSE? A. Alkyllithium reagents (RLi) add to the carbonyl group of aldehydes and ketones. B. Grignard reagents (RMgBr) add to the carbonyl group of aldehydes and ketones. C. Alkyllithium and Grignard reagents do not add to esters. D. Grignard reagents are prepared in ether or tetrahydrofuran (THF). |
C. Alkyllithium and Grignard reagents do not add to esters. |
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Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens(largest δ value first, smallest value last). a) CH3OCH2CH3; b) CH3CH2CH3; c) Cl2CHCH2CH3; d) ClCH2CH2CH3 |
a > c > d > b |
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Which of the following statements regarding the Diels–Alder reaction is TRUE? A) The diene must be s-cis and the major product is usually the endo product. B) The diene must be s-trans and the major product is the endo product. C) The diene must be s-cis and the major product is the exo product. D) The diene must be s-trans and the major product is the exo product. |
A) The diene must be s-cis and the major product is usually the endo product. |
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When benzene undergoes hydrogenation in the presence of a catalyst, the energy that is released (the heat ofhydrogenation) is A) the same as for cyclohexatriene. B) the same as for 1,3-cyclohexadiene. C) the same as for 1,4-cyclohexadiene. D) less than for 1,3-cyclohexadiene. |
D) less than for 1,3-cyclohexadiene. |
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Which of the following aromatic compounds undergoes Friedel–Crafts alkylation with methyl chloride andaluminum chloride? A) benzoic acid B) nitrobenzene C) aniline D) toluene |
D) toluene |
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Which of the following compounds does NOT give a tertiary alcohol upon reaction with excessmethylmagnesium bromide? A) 3-methylpentanal B) ethyl benzoate C) 4,4-dimethylcyclohexanone D) 4-heptanone |
A) 3-methylpentanal |
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Predict which of the following compounds will have a lower boiling point than 1-butanal. A) 1-butanol B) 2-butanol C) 1-butene D) butanoic acid |
C) 1-butene |
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What ylide is needed to make 3-ethyl-3-heptene from 3-pentanone in a Wittig reaction? A) Ph3P=CH-CH2-CH3 B) Ph3P=CH(CH2CH3)2 C) Ph3P=CH-CH2CH2CH3 D) Ph3P=CH2 |
C) Ph3P=CH-CH2CH2CH3 |
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Which of the following compounds will react most rapidly with water? A) acetone B) acetyl chloride C) acetic anhydride D) ethyl acetate |
B) acetyl chloride |
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What is the product formed when benzonitrile is treated with phenylmagnesium bromide followed by acidhydrolysis? A) benzophenone B) benzyl alcohol C) benzaldehyde D) triphenylmethyl amine |
A) benzophenone |
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Which compound is formed when the enolate of 2-methylcyclohexanone, formed from lithiumdiisopropylamide (LDA), reacts with methyl iodide? |
B |
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What is the name of the following compound? |
lithium diisopropylamide |
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Predict the product of the following reaction. Benzenediazonium chloride + CuCN → A) Ph2CuCl B) Ph–CN C) Ph2CuLi D) Ph–N=N–CN |
B) Ph–CN |
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Which of the following compounds form the highest percentage of gem-diol at equilibrium? A) CH3CH2CH2CHO B) CH3CH2COCH3 C) CH3CF2CHO D) CH3CH2CHO |
C) CH3CF2CHO |
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Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution. CH3CH2CH2CONH2 (W); CH3CH2CH2COCl (X); CH3CH2CH2COOCH2CH2CH3 (Y); (CH3CH2CO)2O (Z) |
W < Y < Z < X |
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Rank the following three compounds in the order of increasing basicity. |
b < a < c |
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What reagent(s) is/are needed to convert 1−ethylcyclohexene into1,2−dibromo−1−ethylcyclohexane? A. H2, Pd−C B. HBr, ROOR C. HBr D. Br2 |
D. Br2 |
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Match 1H NMR spectra with compounds. |
C. Spectrum E is from compound X, and spectrum F is from compound Z. |
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Which of the following compounds are aromatic? |
Compounds S, T, U, V, X, Z only. |
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Which labeledH atom is most acidic? Which labeled H atom is least acidic? |
Hb is most acidic because its conjugate base is aromatic; Hc is least acidic because its conjugate base isantiaromatic. |
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Explain why 2,2,5,5−tetramethyl−3−hexyne can't be made using acetylide anions. Selectthe single best answer. A. The 1° alkyl halide is too crowded for nucleophilic substitution. B. It has an internal alkyne; and internal alkynes cannot be made using acetylide anions. C. The 2° alkyl halide is too crowded for nucleophilic substitution. D. The 3° alkyl halide is too crowded for nucleophilic substitution. |
D. The 3° alkyl halide is too crowded for nucleophilic substitution. |
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Which is it |
X |
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Assign carbon-13 NMR signals to each carbon in the compound shown. |
C1, C2, C3 and C4 appear at 23, 70, 32 and 10 ppm, respectively. |
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Provide reagents for the following multistep synthesis. |
Reagent X is Cl2 and water; reagent Y is NaH; reagent Z is first NaC≡CH, then water. |
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Using the pKa values given, which of the following bases are strong enough to deprotonate CH3COOH(pKa = 4.8)? |
Only bases V, Z and X are strong enough. |
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Identify the reactants required for the formation of an enamine. A) A ketone or an aldehyde and a secondary amine B) A ketone or an aldehyde and a primary amine C) An ylide and a primary amine D) An ylide and a secondary amine |
A) A ketone or an aldehyde and a secondary amine |
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What 10-carbon compound will undergo ozonolysis to give 2,4-pentadione as the only product? A) 1,2-Dimethylcyclopropene B) 1,6-Cyclodecadiene C) 1,2,4,5-Tetramethyl-1,4-cyclohexadiene D) 2,4-Dimethyl-1,4-cyclooctadiene |
C) 1,2,4,5-Tetramethyl-1,4-cyclohexadiene |
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Which reagent would be used to reduce the alkene in cyclopentenone? A) NaBH4 B) LiAlH4 C) 1 equivalent H2 and catalytic amount of Pd/C D) DIBAL-H |
C) 1 equivalent H2 and catalytic amount of Pd/C |
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Which of the following molecules would give an IR spectrum with the following peaks: 1650 cm-1; 2900 cm-1; 3040 cm-1; 3300 cm-1 (weak); 3400 cm-1 (weak) |
Compound Y |
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Identify the hemiacetal carbon atom in this structure. |
B |
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An unknown compound X has the molecular formula C6H14O. X shows a strong peak in its IR spectrum at3000 cm–1. The 1H NMR spectral data of X are given below. What is the most likely structure of X? |
Compound C |
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Which of the following alkenes undergo allylic bromination to form a single monobrominated product (notincluding stereoisomers)? |
A |
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Which of the following compounds give one singlet in 1H NMR spectra? |
Compounds S, U, W, Z |
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Which of the following compounds matches or match the IR spectrum shown? |
X |
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What is the first step in the general mechanism for electrophilic aromatic substitution? A) Protonation of the aromatic ring B) Deprotonation of the aromatic ring C) Addition of the electrophile to the aromatic ring D) Loss of the electrophile from the aromatic ring |
C) Addition of the electrophile to the aromatic ring |
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Why is the nitro group a meta director? A) Because it is sterically very large B) Because it adds electron density to the meta position, thus activating it C) Because it stabilizes the intermediate cation D) Because it removes more electron density from the ortho and para positions than the meta position, thusdeactivating the meta position less |
D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less |
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How could you separate the following compounds? |
Make a weakly basic aqueous solution, then extract with an organic solvent |
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Rank the following from most to least acidic. |
Compound B > Compound C > Compound A |
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What is the missing reagent in the reaction below? |
(Picture 30) Compound B |
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What is the product of the following reaction? |
Compound D |
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Which reagent would bring about the following transformation? A) LiAlH4 C) Br2, light B) FeCl3 D) Basic KMnO4 |
D) Basic KMnO4 |
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What reagent(s) is (are) needed to add NO2 to benzene? A) HNO3, HCl B) HNO3, H2SO4 C) NO2(g) D) NO2, CCl4 |
B) HNO3, H2SO4 |
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An electron donating group attached to a benzoic acid will: A) Make the benzoic acid less acidic B) Make the benzoic acid more acidic C) Deactivate the benzene ring D) Not change the acidity of the benzoic acid |
A) Make the benzoic acid less acidic |
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Which of the reagents are suitable for the following transformations? A. (1) SOCl2; (2) benzylamine (PhCH2NH2) B. Benzylamine, DCC (N,N′-dicyclohexylcarbodiimide) C. (1) Benzylamine; (2) heat to more than 100 °C D. All above |
D. All above |
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For proton and carbon NMR spectra, which statement is NOT correct? A. Downfield direction is the direction from right to left in the spectra or from lower chemical shift to higherchemical shift B. More deshielded nucleus will have a larger chemical shift than less deshielded nucleus C. Normally, hydrogen on a tertiary carbon has a larger chemical shift than that on a primary carbon D. Hydrogens on benzene ring are deshielded due to the current from circulating π electrons, the same is truefor alkenes and alkynes |
D. Hydrogens on benzene ring are deshielded due to the current from circulating π electrons, the same is true for alkenes and alkynes |
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Rank the following enolates according to their stability from most stable to least stable. |
(pic 34) X > W > Y > Z |
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Select the appropriate reagents for the following transformation. A. (1) DIBAL-H; (2) water B. (1) LiAlH4; (2) water C. (2) NaBH4; (2) water D. All above |
(pic 35) A. (1) DIBAL-H; (2) water |
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What are the products of the following two reactions? |
Product U is Z; product V is W |
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For molecular orbital (MO) theory, which of the following is NOT correct? A. An MO that has more nodes is higher in energy than an MO that has fewer nodes B. HOMO has higher energy than LUMO C. The lowest energy MO formed by the six p atomic orbitals in benzene is the MO in which all the p orbitalsare in phase D. The energy is not lowered when atomic orbitals form MOs |
B. HOMO has higher energy than LUMO |
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What is the product of the following multiple step reaction? |
Compound Z |