ACS Organic Chemistry Practice Test

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• In SN2 reactions at a stereocenter, what is the resulting stereochemical outcome?
• Which statement describes Boyle's law?
• Which method is commonly used to separate components of a homogeneous mixture?
• In VSEPR theory, electron pairs around the central atom arrange themselves to:
• Which principle does VSEPR theory rely on to determine molecular geometry?
• Covalent bonds are formed when:
• Increasing the concentration of reactants generally has what effect on the rate of a chemical reaction?
• Which description correctly defines the unit of specific heat capacity?
• Which equation represents a decomposition reaction?
• Which expression correctly defines activation energy Ea?
• In adding or subtracting measurements, how should you round the result?
• Percent by mass is defined as what?
• What does VSEPR stand for?
• PBr3 converts alcohols to which product?
• Why is the pressure of a gas directly proportional to temperature?
• Among halide leaving groups in substitution reactions, which is the best leaving group?
• Which factor directly lowers the activation energy of a reaction?
• In infrared spectroscopy, a strong absorption near 1700 cm^-1 indicates which functional group?
• In peroxides, what is the oxidation state of oxygen?
• If a compound has molecular formula C6H6 and empirical formula CH, what is the smallest whole-number multiple that relates them?
• If a system has 6 π electrons, what is n in the 4n+2 rule?
• Which statement correctly describes ionic bonding?
• Which description best characterizes ionic compounds?
• Which statement describes a decomposition reaction?
• What is the oxidation number of oxygen in most compounds?
• Which statement about electronegativity is accurate?
• What does ΔH represent in a chemical reaction?
• Grignard reagents require anhydrous conditions and what solvent?
• If the temperature increases while the volume is held constant, what happens to the pressure?
• What is Avogadro's number?
• Why is the pressure of a gas directly proportional to the number of particles?
• What is the sum of oxidation numbers for a polyatomic ion?
• In 1H NMR, a tert-butyl group typically appears as a singlet around what chemical shift?
• For SN1, what stereochemical outcome is observed when starting from a chiral substrate?
• Which gas will have the highest rate of effusion at the same temperature?
• In free-radical polymerization, which species propagates the chain growth?
• In a reaction with stoichiometry A + 2B → products, if you start with 3 moles A and 3 moles B, which reagent is limiting?
• Which transformation converts an alcohol into a good leaving group that can be displaced in SN2?
• Molarity is defined as which ratio?
• Do columns or rows in the periodic table have repeating patterns?
• Which statement is true about Avogadro's number?
• What term describes the closeness of measurements to the true value?
• Hydroboration-oxidation of an alkene yields what type of alcohol and is Markovnikov or anti-Markovnikov?
• What is the sum of oxidation numbers for a neutral compound?
• What is the value of the ion-product of water, Kw, at 25°C?
• Horner-Wadsworth-Emmons reaction tends to give predominantly which stereochemical outcome in alkenes?
• In an endothermic process, heat flows into the system. What is the sign of q?
• In nucleophilic aromatic substitution, what leaving group and substituent pattern typically enable the reaction?
• The hydration of a terminal alkyne with HgSO4/H2SO4 furnishes what product?
• Are leading zeros significant?
• How do you determine polarity?
• Which oxidation yields carboxylic acids from primary alcohols? PCC or Jones?
• What are the units for the specific heat capacity?
• What are the units for heat capacity?
• In SN2 reactions, what happens to the stereochemistry at a chiral center?
• In E2 elimination, which factor influences the major product, and what does a bulky base favor?
• At standard temperature and pressure, 1 mole of an ideal gas occupies how many liters?
• Which equation represents a combination reaction?
• Infrared spectroscopy: the carbonyl stretch of ketones and aldehydes typically occurs near which wavenumber?
• Molar mass, as a concept, is defined as which of the following?
• What is a common byproduct of the Wittig reaction?
• Activation energy is defined as the energy difference between which two entities?
• Williamson ether synthesis uses what reagents?
• In an E2 elimination using a bulky base, which product is the Hofmann product?
• Jones oxidation of a primary alcohol yields which product?
• Which statement correctly distinguishes molecular formula from empirical formula?
• In electrophilic aromatic substitution, which substituent directs predominantly to ortho and para positions?
• Fischer esterification requires which two substrates and catalyst?
• Which of the following is an example of a homogeneous mixture?
• What is the expression for the equilibrium constant for the reaction A + B ⇌ C + D?
• Which species is most reactive toward nucleophilic acyl substitution?
• Which explanation best accounts for the favored endo orientation in a Diels-Alder reaction?
• According to Gay-Lussac's law (at constant volume), what happens to pressure when temperature increases?
• Which species is least reactive toward nucleophilic acyl substitution?
• Which statement best describes the effect of a catalyst?
• The Knoevenagel condensation involves condensation of aldehydes/ketones with active methylene compounds under base catalysis to yield what?
• Where is the atomic mass number indicated on a chemical symbol according to the material?
• What is the product when an alcohol is treated with p-toluenesulfonyl chloride (TsCl) in the presence of a base?
• Which reagent combination would you use to hydrate a terminal alkyne to a methyl ketone?
• In an epoxide ring opening under basic conditions, which carbon is attacked?
• In a Diels-Alder reaction, which product orientation is typically favored and why?
• Chromatography is used to separate components of what type of mixture?
• Which conditions favor the formation of enolates with LDA versus NaH or OH-?
• In electrophilic aromatic substitution, what kind of substituent is typically a meta-director?
• Which equation expresses dilutions?
• Dalton's Law of Partial Pressures states that the total pressure of a gas mixture is the sum of the partial pressures of its components.
• In a Michael addition to an α,β-unsaturated carbonyl compound, where does the nucleophile attack?
• The oxidation product of primary alcohols using PCC vs Jones oxidation is different; what is produced by PCC?
• Which statement is NOT true about significant figures?
• Specific heat capacity is given by which formula?
• Reaction of a Grignard reagent with an epoxide yields what type of product?
• According to Charles' Law, if the temperature doubles at constant pressure, what happens to volume?
• Graham's law scenario: If Gas A has half the molar mass of Gas B, what is Rate A / Rate B according to Graham's law?
• In an E2 reaction, what geometric arrangement is required between the leaving group and the hydrogen being abstracted?
• Which statement about leading zeros is true?
• In an E2 elimination, which statement correctly describes the regioselectivity under basic vs acidic conditions?
• Tosylate formation of an alcohol commonly uses which reagent and base?
• Molality is defined as what?
• In Knoevenagel condensation, the newly formed double bond lies between which carbons of the carbonyl compound?
• What does the Atomic Mass Number represent?
• In the periodic table, where is atomic size generally larger?
• From a reaction energy diagram, which expression gives ΔH, the enthalpy change?
• How do you distinguish E and Z isomers for a disubstituted alkene?
• Which law describes the rate of effusion being inversely proportional to the square root of the molar mass?
• Which equation represents a double replacement reaction?
• If a polyatomic ion contains a -3 charge, what is the sum of oxidation numbers for that ion?
• How many significant figures are in 50.0?
• In an epoxide ring opening under acidic conditions, which carbon is attacked?
• What is the sum of oxidation numbers for a polyatomic ion? (reiterated)
• Which statement ranks reactivity correctly from most to least reactive for nucleophilic acyl substitution?
• In multiplying or dividing measurements, how should you round the result?
• Nitrile hydrolysis yields what under acidic or basic conditions?
• Molar mass is expressed in which units?
• Distillation separates components based on differences in what property?
• Which area of the periodic table shows greater ionization energy?
• Which formula correctly computes Percent Error?
• What is ΔH defined as in a chemical reaction?
• Which substance exhibits hydrogen bonding?
• Which statement best describes the expression for the equilibrium constant Keq for a general reaction?
• What are the values for STP?
• Which equation represents a single replacement reaction?
• Are trailing zeros after the decimal significant?
• A tert-butyl group contains how many equivalent protons?
• SOCl2 converts alcohols to which product?
• Grignard reaction with carbon dioxide followed by acid workup yields what product?
• Dalton's law of partial pressures states that the total pressure of a gas mixture is equal to:
• In a neutral atom, the number of electrons equals the number of protons. Which statement is true?
• Which technique is used to separate components of a homogeneous mixture?
• In an aldol condensation, the dehydrated product is best described as which type of compound?
• In a combustion reaction, which products are typically formed?
• According to the material, the Atomic Mass equals which quantity?
• What is the oxidation-number sum for NH4+?
• Which gas travels fastest at the same temperature?
• In electrophilic aromatic substitution, nitro groups direct new substituents to which position?
• The 1H NMR signal for a proton on an alkene adjacent to an electron-withdrawing group typically appears downfield or upfield?
• The concept of aromaticity requires a planar cyclic conjugated system with how many π electrons?
• Keq is generally considered to be dimensionless under standard conditions. Which statement best captures this?
• Is water polar?
• A neutral atom with 12 protons and 12 electrons has what electric charge?
• In SN1 reactions, which intermediate forms during the rate-determining step?
• Which statement is true about Grignard reagents?
• What is an isotope?
• The reactivity order for nucleophilic acyl substitution is acid chloride > anhydride > ester > amide. True or false?
• Percent composition is calculated as?
• Nucleophilic aromatic substitution typically requires what kind of substituent pattern on the ring?
• What are the three types of intermolecular forces?
• Which of the following is a homogeneous mixture?
• Which statement best describes an ionic bond?
• Transesterification requires what?
• What are the main products of ozonolysis of an alkene after reductive workup?
• Calorimeters are used to determine which property?
• Graham's Law of Effusion provides the relation Rate A / Rate B = sqrt(M_B / M_A).
• Which statement about electronegativity is accurate, including noble gases?
• The Wittig reaction forms what type of product from aldehydes/ketones and phosphonium ylides?
• Which of the following is NOT a requirement for aromaticity?
• Which statement best describes a homogeneous mixture?
• Which area of the periodic table exhibits greater metallicness?
• In a reaction with stoichiometry A + 2B → products, if you have 1 mole of A and 1 mole of B, which reactant is limiting?
• Which term describes the closeness of a set of measurements to each other?
• Starting from a chiral substrate, SN1 typically yields which type of mixture?
• Which oxidation condition would convert a primary alcohol to an aldehyde rather than to a carboxylic acid?
• Which statement distinguishes molarity from molality?
• Which statement is true about Kw at a given temperature?
• Which expression represents a single replacement reaction?
• What is the rate-determining step in SN1 reactions?
• The Malonic ester synthesis uses diethyl malonate to form what type of product after alkylation and decarboxylation?
• Malonate ester hydrolysis and decarboxylation is a typical route to synthesize what kind of chain?
• Which solvent and substrate combination most strongly favors SN1 over SN2?
• A carbanion stabilized by resonance or hyperconjugation: which is more stable, a benzylic carbanion or a standard alkyl carbanion?
• Calorimeters are used to measure which of the following properties?
• Which statement about oxidation numbers is true for a neutral molecule such as CO2?
• What is the effect of increasing surface area on collision frequency?
• In the O2 molecule, what is the oxidation state of each oxygen atom?
• In an exothermic process, heat flows out of the system. Which statement is true about q?
• If a solution is saturated, is there left over solute?
• Which statement about the molar volume of an ideal gas at STP is true?
• Across a period, how does atomic size change?
• Which equation describes a combustion reaction, as commonly illustrated here?
• What is a common disconnection strategy to form an amide from a carboxylic acid derivative and an amine?
• Which equation correctly represents the heat q in terms of mass m, specific heat capacity c, and temperature change ΔT?
• Swern oxidation of a primary alcohol yields which product?
• Which statement correctly differentiates aldol condensations from Claisen condensations in terms of substrates and products?
• How does increasing surface area affect the reaction rate?
• Which of the following best describes Kw’s dependence on temperature?
• Which state of matter has the greatest kinetic energy?
• Why is the volume of a gas inversely proportional to pressure?
• In ozonolysis with reductive workup, if the alkene is terminal, what is produced as one of the fragments?
• Which substituent on an aryl ring activates it toward nucleophilic aromatic substitution by stabilizing the Meisenheimer complex?
• In a reaction mixture of NaOH 1 mole and HCl 2 moles, which is the limiting reactant?
• In mass spectrometry, what does a molecular ion M+ indicate?
• Which equation demonstrates Charles' law, where volume is directly proportional to temperature at constant pressure?
• For a conjugate acid-base pair, which relation is correct at a given temperature?
• What do you call a solid changing to a gas?
• Grignard reaction with formaldehyde followed by workup yields what product?
• In an E2 reaction, which geometric arrangement is required between the leaving group and the β-hydrogen?