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Definitions |
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Is the cycloheptatrienyl cation aromatic?
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yes
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Consider the molecules pyridine and pyrrole and choose:
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Both are aromatic
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Nucleophilic aromatic substitution reactions are best accomplished when the aromatic substrate contains
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electron-withdrawing groups
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The molecular formula for aniline is
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C6H7N
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T/F: Friedel-Crafts acylation [electrophilic aromatic substitution] reactions require a Lewis Acid catalyst.
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True
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How many hydrogen atoms are there in benzyne?
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4
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T/F: The energies required for NMR spectroscopy are much smaller than those required for IR spectroscopy.
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true
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The proton bonded to oxygen in carboxylic acids, in 1H NMR, resonates
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far downfield
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Trimethylsilyl ethers are relatively unreactive but do react with
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aqueous acids
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When 2-methyl-1,3-cyclohexadiene is allowed to react with HCl (1 eq), which of the following does not form?
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5-chloro-1-methylcyclohexene
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nitrobenzene is allowed to react with HNO3/H2SO4, a dinitrobenzene is formed. The 13C NMR spectrum of this dinitrobenzene has how many signals?
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4
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T/F: Signal averaging and FT-NMR are important techniques that aid in the collection of 13C NMR data.
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true
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The chlorine atoms in I (on the board) are
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exo
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The molecule cyclobutane has how many peaks in its 13C NMR spectrum?
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1
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1,3-Cyclopentadiene, at room temperature, reacts with itself to form a molecule that has exactly how many hydrogen atoms bonded to sp2-hybridized carbon atoms?
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4
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Consider the -CH2- and -CH3- hydrogens in butane. When comparing the -CH2- and -CH3- hydrogens in butane, it is said that they are...
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non-equivalent
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Which of the following is most generally utilized when testing for the presence of C=O bonds?
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IR spectroscopy
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The molecule 3-phenyl-2-butanol contains how many hydrogen atoms?
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14
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Consider the six -CH3- hydrogens in butane. These hydrogens are...
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homotopic
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Is the heat of hydrogenation of benzene
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less negative than expected
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The Diels-Alder dimerization of 1,3-cyclopentadiene results in a product that has how many carbon atoms that are bonded to exactly one hydrogen atom?
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8
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Consider the cyclopropenyl cation, radical and anion (C3H3+; C3H3.; C3H3-, respectively). Which of the three of these is considered to be aromatic?
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the cation
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Halogen atoms are considered to be ortho-para directing groups (in EAS reactions) because, via resonance, they
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donate electrons
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In the Diels-Alder sense, the molecule benzoquinone
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has four hydrogen atoms and is a dienophile
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The bond between carbon atom #s 2 and 3 in butadiene is
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shorter
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Benzaldehyde contains how many hydrogen atoms?
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6
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Where would p-nitrotoluene be most likely to undergo monobromination?
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ortho to the methyl group
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Which of the following does not form when 1,3-butadiene is allowed to react with HBr?
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2-bromo-2-butene
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There are how many peaks in the carbon-13 spectrum of cyclopentanol?
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3
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Benzoic acid, when allowed to react with HNO3/H2SO4, is transformed into
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m-nitrobenzoic acid
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There are how many unshared pairs of electrons in the best Lewis Dot structure for the nitronium ion?
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4
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When vinylbenzene is allowed to react with H2 (Pd catalyst) at atmospheric pressure and room temperature (mild conditions), the main organic product that results is
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ethylbenzene
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You think a given unknown may have a C=O bond. Which instrumental technique is preferred to confirm your thought?
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IR
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Another name for styrene is vinyl benzene. When vinyl benzene is allowed to react with H2, Pd (in ethanol), the organic product that forms is
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ethyl benzene
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T/F: A standard NMR spectrum has, on its left side, the downfield, deshielded side.
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true
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T/F: solvation effects play important roles in the relative aqueous-phase acidities of simple alcohols
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true
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Which of the following regions of the electromagnetic spectrum is the region of longest wavelength?
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infrared
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The unsaturation present in benzene is
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more difficult
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Consider the four -CH2- hydrogens in butane. These hydrogens are...
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enantiopic
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The molecule 6-chloro-1-methylcyclohexene contains how many carbon atoms that are bonded to exactly two hydrogen atoms?
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3
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When benzene is converted into chlorobenzene (using FeCl3 and Cl2), the reaction proceeds through a
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carboncation intermediate
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If reactant A can form two products (B and/or C)...and both reactions (A-->B and A-->C) are not reversible, this set of reactions is said to be under
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Kinetic Control
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How many carbon absorptions are observed in the 13C NMR spectrum of para-Bromoacetophenone?
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6
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T/F: benzynes are reactive intermediates that are likely to undergo elimination reactions.
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False
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How many bonding molecular orbitals are there in 1,3-butadiene?
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2
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Which of the following does not possess a conjugated system of pi electrons?
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1,4 pentadiene
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When tert-butylbenzene is allowed to react with KMnO¬4¬ (in water), what happens?
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there is no reaction
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Which of the following has a max with the longest wavelength?
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1,3,5,7-octatetraene
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Adding molecular hydrogen to 1,4-pentadiene is (fill in the blank) _______ than adding molecular hydrogen to 1,3-butadiene.
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more exothermic
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When benzene is allowed to react with acetyl chloride (in the presence of AlCl3), the molecular formula for the organic product that results is
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C8H80
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Generally speaking, if you have a reaction that can go to two products (one the 'kinetic product' and the other the 'thermodynamic product')...raising the temperature at which you carry out the reaction increases the likelihood that which product will for
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the thermodynamically-controlled product
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Which of the following is least reactive in electrophilic aromatic bromination reactions?
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nitrobenzene
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Benzene is aromatic. Evidence for the 'aromaticity' of benzene is that its heat of hydrogenation (forming cyclohexane) is
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less exothermic than expected
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There are how many hydrogen atoms in a single molecule of naphthalene?
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8
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Consider the two -CH2- hydrogen atoms in R-2-Butanol. These two hydrogens are...
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diastereotopic
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The molecule pyrrole contains how many hydrogen atoms?
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5
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Benzoquinone, in Diels-Alder reactions, is a suitable...
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dienophile
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Reaction conditions that include high temperatures generally favor
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thermodynamic control
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T/F: In the absence of an external magnetic field, the spins of magnetic nuclei are oriented randomly.
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true
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Pyridine..
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contains five hydrogen and is aromatic
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When 1,3-cyclopentadiene is allowed to react with a strong Bronsted base, the main product that forms is
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the aromatic cyclopentadienide anion
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The Diels-Alder reactions discussed in class occurs in
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a single step
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When primary alcohols are allowed to react with CrO3, the organic product that forms is...
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a carboxylic acid
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The most stable geometry for 1,3,5,7-cyclooctatetraene is one in which it is
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non-planar
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Diels-Alder reactions require a diene and a dienophile. The reactions occur best when
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the dienophile copntains electron withdrawing groups
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When molecular bromine reacts with FeBr3, a species forms which acts as an electrophile (and subsequently reacts with benzene). That species is
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BR+
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presence of electron-withdrawing groups on the aromatic ring are necessary if one desires to complete a nucleophilic aromatic substitution reaction because the organic intermediate in this reaction is a...
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Carbanion
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Which of the following is not aromatic?
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benzene, cyclopentadienyl anion, cycloheptatrieny cation are all aromatic
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1H NMR spectra for dimethyl ether (CH3OCH3) and acetone (CH3COCH3) each consist of one peak. Which peak is most downfield?
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the ether
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Consider the reagent NBS. The 'B' refers to
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Bromo
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Consider reactant A, which can be converted into product B (in one reaction) or product C (in a different reaction). If A forms B reversibly, and A also forms C reversibly...the ratio of B formed to C formed (i.e. [B]/[C]) depends primarily on
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relative product stabilities
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Is the cycloheptatrienyl cation aromatic?
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yes
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The molecule benzoquinone contains how many hydrogen atoms?
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4
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Which of the following is considered to be 'conjugated'?
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1,3 butadiene
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The fact that halogen substituents are ortho-para directing substituents is due to their
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electron-donating resonance effect
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The 'best' Lewis Structure for NO2+ puts what formal charge on oxygen?
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neutral
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There are six benzene molecular orbitals. In the ground state of benzene, how many of these orbitals are bonding?
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3
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T/F: the Diels-Alder reaction is considered to be stereospecific.
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True
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The 'L' in LUMO represents.
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?
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1,3-cyclobutadiene is
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an extremely unstable diene
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The hydrogenation reactions of alkenes (for example, hydrogen + ethene = ethane) are typically exothermic reactions. Which of the following dienes, when allowed to react with excess hydrogen, have heats of reaction that are the most negative (i.e. the mos
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1,4 pentadiene
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T/F: 2,2,2-trifluoroethanol is a weaker acid than ethanol.
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false
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The molecule naphthalene contains how many pi electrons?
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10
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When 1-chloro-2-nitrobenzene is converted into 2-nitrophenol (using KOH), the reaction proceeds through a
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carbanion intermediate
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The 1,4-addition product resulting when HBr (1 eq) is allowed to react with 1,3-butadiene (1 eq) is...
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1-bromo-2-butene
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Draw the molecule 1-chloro-2-nitrobenzene and number all six of the benzene carbons. Which carbon would you expect the next electrophilic aromatic substitution to occur? In other words, if 1-chloro-2-nitrobenzene is subjected to conditions resulting in it
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#4 and #6
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The best Lewis Dot structure for NO¬2+ is one that has what formal charge on N?
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positive
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The hydrogenation of benzene is
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exothermic and endothermic process
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The molecule 'benzyne' undergoes reactions that are best described as
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addition reactions
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Aniline contains which of the following?
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nitrogen
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How many hydrogen atoms are there in a single molecule of p-bromoaniline?
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6
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The molecular formula for naphthalene is
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C10H8
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When ketones are allowed to react with NaBH4, the organic product that forms is
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secondary alcohol
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T/F: water is similar to alcohols and phenols in that all three are both weakly basic and weakly acidic.
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true
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Where would p-methylphenol be most likely to undergo monobromination?
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ortho to the -OH group
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T/F: Friedel-Crafts alkylation and acylation reactions both result in the formation of new C-C bonds
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true
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The conversion of benzene into nitrobenzene requires nitric acid and what other reagent?
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sulfuric acid
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How many carbon resonance lines would you expect in the 13C NMR spectrum of 1-methylcyclohexene?
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7
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Consider the pi molecular orbitals for 1,3-butadiene. Which are lower in energy?
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bonding orbitals
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Via resonance (when adjacent to a carbocation) a chlorine atom
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donates electrons
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In 2-phenylheptane, how many carbon atoms are bonded to exactly two hydrogen atoms?
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4
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Consider the molecule 2-chloropropane...there are two 'sets' of signals in its 1H NMR spectrum. Which 'set' is more downfield
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the set resulting from one hydrogen
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Which of the following is most reactive in electrophilic aromatic bromination reactions?
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aniline
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Which of the following alkenes has the longest max?
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1,2,5,7-octatetraene
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Consider the molecule 2-bromoaniline. Which carbon atom is most reactive toward further electrophilic aromatic substitution in 2-bromoaniline?
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#4
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One of the following terms can describe a pair of hydrogen atoms that are likely to show different 1H NMR absorptions. Which one?
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diastereotopic
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The molecule anthracene contains how many carbon atoms that are bonded to exactly zero hydrogen atoms?
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4
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A photon of infrared radiation has________energy than a photon of ultraviolet radiation (p 500)
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less
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2,5-Dimethylphenol contains how many hydrogen atoms?
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10
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The anionic portion of the reagent 'potassium tert-butoxide' contains how many atoms?
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14
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1,3,5,7-cyclooctatetraene is
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tub-shaped molecule
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Simple alkyl groups, when attached to benzene in EAS reactions, are said to be
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electron donating and ring activating
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Extended conjugation in an organic molecule results in
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longer-wavelength uv-visible absorptions
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When nitrobenzene is allowed to react with chlorine (and FeCl3), the primary organic product that results is
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m-chloronitrobenzene
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The molecular formula for 2,5-dimethylphenol contains how many hydrogen atoms?
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10
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How many constitutional isomers are there for 'dinitrobenzene'?
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3
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How many carbon resonance lines would you expect in the 13C NMR spectrum of methylcyclopentane?
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4
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