5
Assign priority (1, 2, 3 or 4) to each of the groups attached to C2 on the following molecule.
1 matches Choice CH(CH3)2 2 matches Choice CH3 3 matches Choice D (Deuterium) 4 matches Choice H
Which of the following is an appropriate name for the compound shown?
1,2-epoxy-2-methylpropane
Which of the following is an appropriate name for the compound shown
1,2-epoxycyclohexane
Rank the following substituents in order of decreasing priority (highest to lowest) according to the Cahn-Ingold-Prelog system. Place the group with the highest priority at the top of the list
1. -CH=CHCH3 2 -CH2CH3
Assign a priority (1, 2, 3, or 4) to each group bonded to the stereogenic center in the molecule shown. Place the group with the highest priority (1) at the top of the list and the group with the lowest priority (4) at the bottom of the list
1. NH2 2. CH2OH 3. CH3 4. H
What is the correct IUPAC name for the compound shown
3-methylheptan-2-ol
Select the correct IUPAC name for the compound shown
4-chloro-4-methylhex-2-yne
Consider a mixture of two enantiomers, A and B. If the mixture contains an excess amount of B and has an ee of 84%, how much of each enantiomer is present? Multiple choice question.
8% A; 92% B
Consider a mixture of two enantiomers, A and B. If the mixture contains an excess amount of A and has an ee of 72%, how much of each enantiomer is present? Multiple choice question.
86% A; 14% B
Select the most stable alkene from the pair shown in the figure
A
Select the structure that corresponds to the IUPAC name 1-ethynylcyclohexanol
A
What is the product formed from treatment of the reaction depicted in the box
A
Which of the following molecules would be expected to be the major product of the E2 reaction shown
A
Which of the following options gives the correct structure for the product formed in the reaction shown
A
Which of the following compounds are more likely to be soluble in an organic solvent than in water?
A B
Select all the structures that represent secondary alkyl halides
A C
What products are possible in the alkyne reaction shown
A D
Which of the following structures represent alcohols
A E
Match each structure with its correct IUPAC name
A matches Choice 3,3-dimethyl-1-pentyne B matches Choice 1-ethynyl-2-methylcyclohexane C matches Choice 4-methyl-2-pentyne
Match the structure of each alkyl halide to its correct IUPAC name
A matches Choice 4-chloro-2-methylhexane B matches Choice 2-chloro-2-methylpentane C matches Choice 1-bromo-2-methylcyclohexane D matches Choice 2-bromo-3,4-dimethylheptane
Match each structure shown to the correct IUPAC name
A matches Choice 6-methyloctan-2-ol B matches Choice 4-ethylhexan-3-ol C matches Choice 4-methylhexan-3-ol D matches Choice 6-methylheptan-2-ol
Match each type of bond in the representation of a tetrahedral stereogenic center with its correct meaning.
A matches Choice Bond is in the plane. B matches Choice Bond is behind the plane. C matches Choice Bond is in front of the plane.
Match the general structure of each compound containing a carbonyl group to the correct name for each compound type.
A matches Choice Carboxylic acid B matches Choice Ketone C matches Choice Acid chloride D matches Choice Ester
Match each reaction shown to its appropriate description
A matches Choice Elimination reaction B matches Choice Substitution reaction
Match the substituent that adds at each carbon indicated if the alkyne shown
A matches Choice H B matches Choice OH
onsider the following reaction coordinate vs. energy diagram
A matches Choice Reactants B matches Choice Transition state C matches Choice Products D matches Choice Ea E matches Choice ΔH°
match the structure of the alkyl halide to its common use
A matches Choice halothane (a general anesthetic) B matches Choice dichloromethane (an important solvent) C matches Choice freon 11 (a refrigerant) D matches Choice teflon (nonstick coating) E matches Choice polyl(vinylchloride) (used in pipes and insulation)
Match the structure of each alkyl halide with its common name
A matches Choice isopropyl chloride B matches Choice propyl chloride C matches Choice tert-butyl chloride D matches Choice isobutyl chloride
Which of the following options correctly describe the general characteristics of a substitution reaction?
A bond breaks and a new bond is formed at the same carbon atom in this type of reaction. Heteroatoms such as oxygen or a halogen are often involved in substitution reactions.
Which of the following options correctly describe a catalyst for a particular reaction? Select all that apply.
A catalyst increases the rate of a reaction. A catalyst may be used up in one step and regenerated in another. A catalyst lowers the activation energy for a reaction.
Which of the following statements correctly describe a meso compound? (Select all that apply.)
A meso compound contains two or more stereogenic centers. A meso compound is achiral. A meso compound generally contains a plane of symmetry.
Which of the following statements correctly describe a meso compound?
A meso compound is achiral. A meso compound generally contains a plane of symmetry. A meso compound contains two or more stereogenic centers.
dentify the correct statement(s) concerning stereoisomers. Multiple select question. A pair of stereoisomers have identical IUPAC names except for a prefix like cis or trans. A pair of stereoisomers differ only in their three-dimensional arrangement of atoms. A pair of stereoisomers can have different functional groups.
A pair of stereoisomers have identical IUPAC names except for a prefix like cis or trans. A pair of stereoisomers differ only in their three-dimensional arrangement of atoms.
A meso compound possesses which of the following structural features? (Select all that apply.)
A plane of symmetry Two or more stereogenic centers
Blank 1: catalyst Blank 2: decreasing, lowering, or reducing
A substance that increases the rate of reaction without being used up in the reaction is called a(n) catalystBlank 1Blank 1 catalyst , Correct Unavailable. Such a substance acts by reactantBlank 2Blank 2 reactant , Incorrect Unavailable the activation energy of the reaction so that a greater proportion of the molecules have sufficient energy to react.
What is a tetrahedral stereogenic center? Multiple choice question. A tetrahedral stereogenic center is a carbon atom bonded to four different atoms or groups. A tetrahedral stereogenic center is a carbon atom bonded to four identical atoms. A tetrahedral stereogenic center is a carbon atom bonded to four identical groups.
A tetrahedral stereogenic center is a carbon atom bonded to four different atoms or groups.
Select all the statements that correctly describe the changes occurring in addition reactions.
A π bond is broken in an addition reaction. Compounds with double bonds can undergo addition reactions.
Match each alkyne reaction to the correct outcome.
Addition of one equivalent of electrophile gives matches Choice an alkene product. Addition of two equivalents of electrophile gives matches Choice a saturated product. Two new bonds form matches Choice in reaction with one equivalent of electrophile. Four new bonds form matches Choice in reaction with two equivalents of electrophile.
Which of the following statements correctly describes why alkanes undergo fewer reactions than other classes of organic compounds
Alkanes are the only class of compounds that do not have a functional group.
Which of the following options correctly describe addition reactions of alkynes? Select all that apply.
All atoms of the electrophile are present in the product. Four new bonds are formed when two equivalents of the electrophile react. The addition of one equivalent of electrophile across the triple bond of the alkyne produces an alkene.
Which of the following best describes the carbon-carbon double bond of an alkene? (Select all that apply.)
All bond angles are 120°. Each carbon has a trigonal planar geometry. Each carbon is sp2 hybridized.
How do alcohols differ from alkyl halides with regard to substitution and elimination reactions
An OH group must generally be converted to a good leaving group before undergoing substitution or elimination.
What functional groups are present in the compound shown
Aromatic ring Amide Carboxy
What functional groups are present in the compound shown?
Aromatic ring Amide Carboxy
Which structure shows the correct product for the reduction reaction of the epoxide?
B
Which products will be formed in the reaction shown
B D
Select all of the structures that are chiral.
B E
Acetylene (ethyne) has C-H bond(s) in which carbon is sp hybridized, thus sequential substitution reactions can occur to form new C-C bond(s).
Blank 1: 2 or two Blank 2: 2 or two
The correct name of the alcohol shown in the figure is
Blank 1: 3-methylcyclohexanol
An alkene is a molecule that contains a carbon-carbon bond.
Blank 1: double
In a(n) eliminationBlank 1Blank 1 elimination , Correct Unavailable reaction, elements of the starting material are "lost" and a new multipleBlank 2Blank 2 multiple , Incorrect Unavailable bond is formed.
Blank 1: elimination Blank 2: pi or π
In the chair conformation for cyclohexane, a larger substituent is more stable in the 1Blank 1Blank 1 1 , Incorrect Unavailable position because this position has more space than the 1Blank 2Blank 2 1 , Incorrect Unavailable position.
Blank 1: equatorial Blank 2: axial
The sum of the exponents of the concentration terms in the rate equation is called the orderBlank 1Blank 1 order , Correct Unavailable of the reaction. A reaction that has the rate law rate = k[A][B] follows productBlank 2Blank 2 product , Incorrect Unavailable - reactantBlank 3Blank 3 reactant , Incorrect Unavailable kinetics overall.
Blank 1: order Blank 2: second or 2nd Blank 3: order
The common name of the alcohol shown below is
Blank 1: propyl or n-propyl
A solution forms when one substance called the soluteBlank 1Blank 1 solute , Correct Unavailable dissolves in another substance called the solventBlank 2Blank 2 solvent , Correct Unavailable. These two substances must be able to interact and therefore must have similar types of fBlank 3Blank 3 f , Incorrect Unavailable forces.
Blank 1: solute Blank 2: solvent Blank 3: intermolecular, nonbonding, non-bonding, or inter-molecular
Two compounds that have the same structure but a different three-dimensional arrangement of atoms are called mBlank 1Blank 1 m , Incorrect Unavailable -isomers, while two compounds with the same formula but different connectivities of atoms are called mBlank 2Blank 2 m , Incorrect Unavailable isomers.
Blank 1: stereo Blank 2: constitutional or structural
A reaction involving only one reactant is said to be nBlank 1Blank 1 n , Incorrect Unavailable, while a reaction involving two reactants in the rate-determining step is described as b
Blank 1: unimolecular Blank 2: bimolecular
Select the product of the reaction shown in the figure
C
Which one of the following options does NOT represent a conformer of propane, looking down the C2-C3 bond?
C
Identify all of the molecules that are capable of hydrogen bonding with water.
C D
Arrange the following compounds in order of decreasing solubility in water
C D A B
Which statement(s) about the compound shown (D = deuterium) is/are correct? Select all that apply.
C2 of the molecule has the R configuration. C2 is a stereogenic center, since it has four different groups attached to it.
Which of the following statements correctly describe the relationship between polarizability and boiling point?
CH3Br is more polarizable than CH3Cl, and so CH3Br will have a higher boiling point
Select the statement that correctly describes the interaction of organic compounds with plane-polarized light.
Chiral compounds rotate plane-polarized light while achiral compounds do not.
Match each substituent with the carbon it will attach to when the alkene shown is reacted with an aqueous solution of Cl2.
Cl matches Choice a OH matches Choice b
Which reagent is necessary to bring about the transformation shown
Cl2, CCl4
1° matches Choice Structure B 2° matches Choice Structure C 3° matches Choice Structure A
Classify each carbocation according to its structure.
Which of the molecules shown is most likely to have a melting point and boiling point similar to propane-1-thiol
Compound A
The Newman projections for four conformations of 2-methylpentane, shown as viewed down the C2-C3 bond, are provided. Match each conformation with its expected position on a graph of dihedral angle vs. energy.
Conformer A matches Choice local energy maximum Conformer B matches Choice overall energy minimum (lowest energy) Conformer C matches Choice overall energy maximum (highest energy) Conformer D matches Choice local energy minimum
Cis-1-methyl-4-phenylcyclohexane exists as a equilibrium mixture of two chair conformations, as shown. ΔGo for the conformational change as written is equal to +4.73 kJ/mol. Select all the statements that correctly interpret this data. Multiple select question. Conformer B is present in a greater concentration at equilibrium. Conformer A is more stable than conformer B. The value of Keq for this conformational change (A to B) is < 1. Conformer B is higher in energy than conformer A
Conformer A is more stable than conformer B. The value of Keq for this conformational change (A to B) is < 1. Conformer B is higher in energy than conformer A.
Compounds A and D will have very similar reaction rates. Compound C will react most quickly because it will form the most stable carbocation.
Consider the structures of the alkyl halides shown, and select all the statements that correctly describe the relative reactivity of these compounds in an SN1 reaction.
What is the relationship between the two structures shown?
Constitutional isomers
Predict the product of the SN2 reaction shown.
D
Which of the following options gives the correct structure for the product formed in the reaction shown
D
what product is shown
D
What is the stereochemical relationship between the two compounds shown?
Enantiomers
is prescribed to reduce cardiovascular risk in patients who have already had a heart attack
Eplerenone Inspra
Which of the following statements correctly describe epoxides?
Epoxides contain polar C-O bonds. Epoxides contain a strained three-membered ring. Epoxides are reactive toward strong nucleophiles and hydrogen halides.
What is the common name for the molecule shown below
Ethyl propyl ether
Rank the nucleophiles shown in order of their nucleophilicity in acetone. Order them with the strongest nucleophile on top and the weakest on the bottom.
H2N; HO; F
When an alkane undergoes combustion, what are the products of the reaction?
H2O CO2
Match the reagents listed to the product formed, if the starting material is a terminal alkyne
H2O, H2SO4, HgSO4 matches Choice methyl ketone i) BH3; ii) H2O2, HO- matches Choice aldehyde
CH3 marked "a" matches Choice axial and above the ring H marked "b" matches Choice equatorial and above the ring Cl marked "c" matches Choice equatorial and below the ring OH marked "d" matches Choice axial and below the ring
Identify each marked substituent on the cyclohexane derivative shown according to its orientation.
Which of the following options correctly describe an organic reaction for which the change in entropy is assumed to be small?
If a reaction has ΔHo < 0, the energy of the products is lower than the energy of the reactants. The product is favored if ΔHo < 0.
How are priorities assigned to each group bonded to a tetrahedral stereogenic center
If two atoms attached to a stereogenic center are the same, assign priority based on the atomic number of the atoms bonded to these atoms. If two isotopes are bonded to the stereogenic center, the isotope with the higher mass number has a higher priority. To assign a priority to an atom that is part of a multiple bond, treat the multiple bond as an equivalent number of single bonds.
Which of the following options correctly describe the characteristics of an elimination reaction? Select all that apply.
In an elimination reaction, two σ bonds are broken and one π bond is formed. Hydrogen is often one of the atoms eliminated in this reaction type. Two atoms or groups are eliminated, usually from adjacent atoms in the compound.
What is the common name for the molecule shown
Isopropyl methyl ether
How are lipids defined?
Lipids are biological compounds that are not soluble in water.
methanol matches Choice wood grain alcohol ethanol matches Choice common gasoline additive 2-propanol matches Choice rubbing alcohol/antibacterial ethylene glycol matches Choice used in automotive antifreeze
Match each alcohol below to its common name/use
A matches Choice 2° alcohol B matches Choice 3° alcohol C matches Choice 1° alcohol
Match each alcohol structure to the appropriate classification
Structure A matches Choice cis alkene Structure B matches Choice trans alkene
Match each alkene structure shown to the appropriate isomeric description
CHCl3 matches Choice chloroform CCl4 matches Choice carbon tetrachloride CH2Cl2 matches Choice dichloromethane
Match each alkyl halide with the name it is most commonly known by, particularly in industry.
Conformer A matches Choice more stable Conformer B matches Choice less stable
Match each conformer of 1-chloroethane correctly according to relative stability
A matches Choice Energy of reactants B matches Choice Transition state C matches Choice Intermediate E matches Choice Energy of products
Match each marked point on the accompanying energy diagram with its correct meaning
Energy is absorbed matches Choice when bonds are broken. Energy is released matches Choice when bonds are formed. Bond breaking matches Choice is an endothermic process. Bond formation matches Choice is an exothermic process.
Match each process correctly to the energy change and sign of ΔHo.
Oxidation results in matches Choice an increase in the number of C-Z bonds. Reduction results in matches Choice a decrease in the number of C-Z bonds. An increase in the number of C-H bonds matches Choice represents a reduction process. A decrease in the number of C-H bonds matches Choice represents an oxidation process.
Match each process to the correct description
A matches Choice cis-2-ethylcyclopentanol B matches Choice 3-methylcyclopentanol C matches Choice 1-isopropylcyclobutanol D matches Choice 1-propylcyclobutanol E matches Choice trans-2-ethylcyclopentanol
Match each structure shown to the correct IUPAC name
A peroxide matches Choice structure B A peroxyacid matches Choice structure A
Match each structure to the correct description.
E1 matches Choice A unimolecular elimination E2 matches Choice A bimolecular elimination
Match each term to the appropriate description
Entropy increases. matches Choice A single starting material forms two or more products. Entropy decreases matches Choice An acyclic compound forms a ring.
Match the description of each reaction with the corresponding change in entropy
A matches Choice Aldehyde B matches Choice Ketone C matches Choice Carboxylic acid D matches Choice Amide
Match the general structure of each compound containing a carbonyl group to the correct name for each compound type.
A matches Choice CH3CH2CH2CΞCH B matches Choice HCΞC- i matches Choice 1. BH3 2. H2O2, OH- ii matches Choice CH3CH2CH2Cl iii matches Choice NaH
Match the precursors and reagents with the appropriate retrosynthetic steps in the analysis shown. A
An exothermic reaction matches Choice has a negative value for ΔHo. An endothermic reaction matches Choice has a positive value for ΔHo. If ΔHo is negative matches Choice the reaction releases heat. If ΔHo is positive matches Choice the reaction absorbs heat.
Match the sign of ΔHo for a reaction with the information this gives about the overall energy change.
When R = CH3, both axial and equatorial conformations occur at equilibrium. The ΔGo value for the conformational change from axial to equatorial when R = C(CH3)3 is approximately -21 kJ/mol. The change from equatorial to axial conformation becomes less favorable as the R substituent increases in size.
Monosubstituted cyclohexanes exist as an equilibrium mixture of two chair conformations, as shown. The values of Keq for some cyclohexane derivatives are provided. Select all the statements that correctly reflect this data.
Consider the molecule shown in the diagram below. Match each group attached to the stereogenic center with its appropriate priority (1, 2, 3, or 4).
OH matches Choice Priority 1 CH=CH2 matches Choice Priority 2 CH3 matches Choice Priority 3 H matches Choice Priority 4
Epoxides undergo a ring-opening reaction when attacked by strong nucleophiles
Optically inactive starting materials give optically inactive products. For an unsymmetrical epoxide, the nucleophile attacks the less substituted C atom. This is an SN2 reaction
Select the correct numbering system for the alkane shown
Option A
Select any reagent(s) below that is/are capable of carrying out the transformation shown in the figure
PBr3 HBr
Select ALL the reagents that are commonly used Cr oxidizing agents for organic reactions.
PCC K2Cr2O7 in aqueous acid CrO3 in H2SO4
Match each oxidizing agent with the correct product formed by reaction with a primary alcohol
PCC in CH2Cl2 matches Choice aldehyde CrO3 in aqueous acid matches Choice carboxylic acid
Match each set of reagents to the correct outcome in the reaction sequences shown
Pathway a reagents are matches Choice H2O, H2SO4. Pathway b reagents are matches Choice i) BH3; ii) H2O2, OH-. An achiral product is produced by matches Choice pathway a. A pair of enantiomers is produced by matches Choice pathway b.
Which of the following options correctly describe the products of the reaction shown? Select all that apply.
Products A and B will be formed. The products are enantiomers.
Select all the statements that correctly describe a polar protic solvent
Protic solvents form intermolecular hydrogen bonds. Polar protic solvents solvate both cations and anions well. Polar protic solvents contain an OH or NH bond
Which of the following reactions involve an increase in entropy? Select all that apply.
Reaction 1 Reaction 4
Which of the following reaction schemes will give the desired product
Reaction A Reaction C Reaction D
Which of the following options correctly identify the reagents necessary to complete the reaction sequence shown correctly? Select all that apply.
Reagent a is a strong and sterically hindered base. The product of the first step is an alkene.
Which of the following statements correctly describe the conventions used when writing equations for organic reactions?
Reagents are often shown above the reaction arrow. The symbol Δ is used to indicate heat. Formulas for inorganic by-products of a reaction are often omitted.
What kind of arrow is shown here?
Retrosynthetic analysis arrow
Designate the configuration of the stereogenic center in the structure shown as R or S. Multiple choice question. S R
S
Match the type of substitution reaction to the appropriate description
SN1 reaction matches Choice The rate is doubled when the concentration of the alkyl halide is doubled. SN2 reaction matches Choice The rate is quadrupled when the concentration of both the alkyl halide and nucleophile are doubled.
Which reaction scheme gives the correct mechanism for the SN2 reaction shown
Scheme A
D and F A and D
Select all of the combinations that will produce the target compound by a substitution reaction.
Structure A Structure B
Select all of the structures that are achiral
Enantiomers rotate plane-polarized light to the same extent. Enantiomers rotate plane-polarized light in opposite directions
Select all statements that correctly describe the relationship between optical rotation and the identity of an enantiomer
This species takes part in methylation reactions. This species is soluble in the aqueous environment in the cell. This species is a sulfonium salt.
Select all statements that correctly describe the structure shown
A and B are diastereomers. A and B have the same connectivity. A and B have the same molecular formula.
Select all statements that correctly describe the two alkenes shown
Structure B Structure C
Select all the chair conformations that correctly represent trans-1,3-dibromocyclohexane
Alkyl groups can stabilize a positive charge by induction. Inductive effects operate through σ bonds only.
Select all the statements that correctly describe inductive effects.
6-bromo-3,4-dimethyloctane
Select the correct IUPAC name for the compound shown
The formation of equal amounts of two enantiomeric products from a single chiral starting material
Select the statement that correctly describes racemization.
There is inversion of stereochemistry, which implies backside attack by the nucleophile.
Select the statement that correctly describes the stereochemical outcome of an SN2 reaction.
Which of the illustrated molecules contain tetrahedral stereogenic centers? (Select all that apply.)
Structure A Structure C Structure D
The Newman projections of four conformers of pentane, drawn as viewed down the C2-C3 bond, are shown. Match each conformer with the correct description of the types of strain it exhibits.
Structure A matches Choice maximum torsional and steric strain Structure B matches Choice no torsional strain, no steric strain Structure C matches Choice maximum torsional strain, no steric strain Structure D matches Choice no torsional strain, some steric strain
Match each chair conformation to the correct name in each case. The chair conformation shown is not necessarily the most stable one for each compound.
Structure A matches Choice trans-1,2-dibromocyclohexane Structure B matches Choice cis-1,3-dibromocyclohexane Structure C matches Choice trans-1,4-dibromocyclohexane Structure D matches Choice cis-1,2-dibromocyclohexane
Which of the following does NOT show a chair conformation for cyclohexane?
Structure B
Select all halides that will NOT undergo SN1 or SN2 nucleophilic substitution reactions.
Structure B Structure D
Select the statement that correctly describes the relative stability of the two chair conformations of trans-1-isopropyl-3-methylcyclohexane (shown).
Structure B is more stable than Structure A.
Select the structure that best represents the transition state for the given overall reaction.
Structure C
Match each structure to the correct description of its relationship to compound A
Structure X matches Choice enantiomer of A Structure Y matches Choice diastereomer of A Structure Z matches Choice identical to A
Which of the following factors affect the value of k, the rate constant for a reaction?
Temperature Activation energy
Which one of the following statements is correct when assigning priorities to the substituents on the stereogenic center shown
The -CH2OH group has a higher priority than the alkene group because O has a higher atomic number than C.
Endothermic Reaction matches Choice Transition state resembles the products. Exothermic Reaction matches Choice Transition state resembles the reactants.
The Hammond postulate describes the structure of the transition state as either resembling product or resembling reactants depending on the energetics of the reaction. Match the relationship given by the Hammond postulate.
A matches Choice Energy of starting material(s) B matches Choice energy of transition state C matches Choice Energy of product(s) Difference between A and B matches Choice Activation energy Difference between A and C matches Choice ΔHo of reaction
The energy diagram for a single-step reaction is shown. Match each point on the graph to the correct designation.
Which of the following statements correctly describes the optical activity of a racemic mixture?
The mixture is not optically active because the two enantiomers cause equal but opposite rotations, which therefore cancel.
ethylene; cracking
The most widely produced organic compound is _____, which is prepared from petroleum by a process called _____.
What is the observed rotation of a sample?
The observed rotation is the angle (α) by which a chiral compound rotates plane-polarized light in a polarimeter.
Which of the following statements correctly describe the stereoisomers of the cycloalkane shown? (Select all that apply.)
The pair of cis isomers are diasteromers of either trans isomer. The two cis isomers are enantiomers of each other.
Which of the following options correctly describe the rate equation of a reaction? Select all that apply.
The rate law is related to the mechanism of the reaction. The rate equation reflects the concentrations of reactants that are involved in the rate-determining step. The rate equation for a reaction is determined experimentally.
The rate equation for the reaction between the alkyl halide (CH3)2CHBr and the hydroxide anion -OH is given by the expression rate = k[(CH3)2CHBr]. Why does this rate equation not include the concentration of the -OH anion?
The rate-determining step involves only the compound (CH3)2CHBr.
Which of the following correctly defines the term stereochemistry
The three-dimensional structure of a molecule
Both reactions are exothermic. The first reaction has a lower activation energy than the second.
The two energy diagrams represent two different reaction pathways. Select all the statements that correctly interpret this data.
Blank 1: vinyl, vinyl halides, or vinylic Blank 2: aryl or aromatic
The two organic halides shown do not undergo SN1 or SN2 nucleophilic substitution reactions. These halides are named dBlank 1Blank 1 d , Incorrect Unavailable and dBlank 2Blank 2 d , Incorrect Unavailable halides.
Which of the following statements correctly describe why enantiomers have different prefixes in their IUPAC names?
They are different molecules with the same bond connectivity but each with a different three-dimensional orientation of atoms.
Which of the following statements correctly describes the C atom bearing the OH group in the compound shown? Multiple choice question. This C is a stereogenic center because the 2 CH2 groups on either side of it are not identical. This C is not a stereogenic center because it has only 3 groups bonded to it. This C is not a stereogenic center because it has 2 CH2 groups bonded to it.
This C is a stereogenic center because the 2 CH2 groups on either side of it are not identical.
Which of the following options correctly interpret the equation shown? Select all that apply.
This reaction involves two sequential steps. The product shows no boron atoms because this element is part of an inorganic by-product. Reaction of the starting material with BH3BH3 occurs before H2O2H2O2 is added to the reaction mixture.
Amine ketone Alcohol
What functional groups are present in the compound shown?
sec-butyl fluoride
What is the common name of the alkyl halide shown?
B and D A and C
Which of the following combinations of species may be reacted to form the target compound shown?
The solvent (protic or aprotic) The nucleophile (strong or weak) The leaving group (good or poor) The alkyl halide (methyl, 1°, 2°, or 3°)
Which of the following factors need to be considered when attempting to determine the mechanism of a substitution reaction
The region of the enzyme to which the substrate binds is called the active site. An enzyme lowers the activation energy for a given reaction.
Which of the following options correctly describe an enzyme?
A reactive intermediate is always at a lower energy than the transition state leading to its formation. A transition state is formed before each reactive intermediate in a reaction. A reactive intermediate is formed in one step and used up in the next.
Which of the following options correctly describe the reactive intermediate(s) of a reaction? Select all that apply.
i) OsO4, ii) NaHSO3, H2O KMnO4 in aqueous OH-
Which of the following sets of reagents will result in syn dihydroxylation of an alkene? Select all that apply.
DMSO acetone
Which of the following solvents would favor an SN2 nucleophilic substitution mechanism? Select all that apply.
Hydration and hydroboration-oxidation both add H2O across a triple bond. Hydration and hydroboration-oxidation of internal alkynes both produce ketones.
Which of the following statements correctly describe hydration and hydroboration-oxidation of alkynes? Select all that apply. Multiple select question.
Nucleophiles and bases have a lone pair or π bond. A nucleophile is a Lewis base that attacks electrophiles other than protons.
Which of the following statements correctly describe nucleophiles and bases
Rate = k[(CH3)3CBr]
Which rate law is consistent with the reaction mechanism shown?
Rate = k[CH3CH2Br][CH3O-]
Which rate law is consistent with the reaction mechanism shown?
Rank the following carbocations in order of increasing stability
a c b
Select the structure(s) of the product(s) of the reaction shown
a c
Fatty acids contain _____. Select all that apply.
a long hydrocarbon chain with a COOH group at one end a long hydrocarbon chain that may include one or more C=C double bonds
Place the following compounds in order of increasing strength of their intermolecular forces. Place the compound with the weakest intermolecular forces at the top of the list and the one with the strongest intermolecular forces at the bottom of the list. The compounds have approximately equal molecular masses
a, c, b
Rank the following compounds in order of increasing boiling point. Place the compound with the lowest boiling point at the top of the list and the one with the highest boiling point at the bottom of the list
a, c, b
The Newman projections for four conformers of pentane, drawn as viewed down the C2-C3 bond, are shown. Arrange these conformers in order of increasing stability (least stable at the top of the list to most stable at the bottom).
a, c, d, b
Match each alkyne to the correct description
acetylene matches Choice used to produce a hot flame in welding torches ethynylestradiol matches Choice synthetic analogue of estrogen histrionicotoxin matches Choice toxin secreted by the skin of a South American frog
A meso compound is a(n) ______ compound containing ______ stereogenic centers
achiral, two or more
Match each compound correctly to the product obtained on reaction with H2 and a metal catalyst
aldehyde matches Choice primary alcohol ketone matches Choice secondary alcohol alkene matches Choice alkane
Halohydrin formation proceeds with _____ addition of Cl and OH across the double bond, producing halohydrin _____ in the reaction shown.
anti, C
Leukotrienes contribute to what physiological response
asthmatic response
Select the correct carbonyl form for the enol shown
b
Select the reaction scheme that gives the correct mechanism for the SN1 reaction shown
b
Which of the compounds shown exhibits the strongest intermolecular forces?
b
Which of the following options correctly identifies the product formed in the reaction shown
b
Rank the following alkyl halides by their rate of SN1 reaction. The alkyl halide that will proceed via the fastest rate is on top and slowest is on the bottom
b a c
Arrange the following compounds in order of decreasing reactivity in an
b c a
Select all of the molecules containing an internal alkyne
b e
The Newman projections for four conformers of 2-methylbutane, drawn viewing down the C2-C3 bond, are shown
b, c, d, a
Which conformation of butane (shown) possesses the greatest amount of steric strain
c
Which of the following options gives the correct structure of the product obtained by complete reaction of the alkyne with HBr
c
Arrange the following compounds in order of increasing reactivity in an SN2 reaction (from least reactive at the top of the list to most reactive at the bottom).
c b A
Rank the alkyl halides shown in order of decreasing reactivity in an E1 reaction
c, a, b, d
Arrange the following chair conformations in order of increasing stability (least stable at the top of the list to most stable at the bottom).
c; b; a; d
Match each type of compound with the correct description of its interaction with polarized light.
chiral matches Choice optically active achiral matches Choice optically inactive
elect the correct definition for each term. Instructions chiral molecule chiral molecule drop zone empty. achiral molecule
chiral molecule matches Choice nonsuperimposable upon its mirror image achiral molecule matches Choice can be superimposed on its mirror image
Match each type of isomer with the correct definition
constitutional isomers matches Choice same molecular formula, different connectivity of atoms enantiomers matches Choice nonsuperimposable mirror images diastereomers matches Choice stereoisomers that are not mirror images stereoisomers matches Choice same formula and structure, different 3-D arrangement
The IUPAC name of the compound shown is
cyclopentane, cycloheptene
What is the major product of the reaction shown
d
What product is formed in the reaction shown
d
What would be the steps and reagents involved to convert acetylene into 2-hexyne
d
Which of the options gives the correct product for the reaction shown?
d
The most widely produced organic compound is _____, which is prepared from petroleum by a process called
ethylene; cracking
Stereoisomers are isomers that differ in the connectivitiy of their atoms. True false question.TrueFalse
false
Stereoisomers have ______________ bond connectivity and ___________ three-dimensional orientation of atoms
identical, different
Stereoisomers have ______________ bond connectivity and ___________ three-dimensional orientation of atoms.
identical, different
Match each structure with the correct designation
internal alkyne matches Choice structure A terminal alkyne matches Choice structure B
A fast reaction will have a _____ rate constant k and a _____ activation energy Ea.
large, low
Which of the following statements describe features found in all elimination reactions? (Select all that apply.)
loss of elements from the α and β carbons of the starting material formation of a π bond in the product
Compound A will have a _____ boiling point than compound B because chlorine is _____ polarizable than iodine.
lower, less
The acetylide anion (see illustration) reacts readily as a good _____ and is also a strong _____.
nucleophile, base
A molecule is always chiral if it contains
one tetrahedral stereogenic center
Select all the IUPAC names that are possible for an alkyne with molecular formula C5H8.
pent-1-yne pent-2-yne 3-methylbut-1-yne
The equilibrium shown favors the _____ because _____.
product; a C=O bond is stronger than a C=C bond
A rate law or rate equation expresses the relationship between the _____ of a reaction and the _____ of the reactants.
rate, concentration
For an organic reaction where the entropy change is considered to be small, a reaction that has a positive value for ΔHo favors the _____ at equilibrium. In such a reaction, the bonds in the products are _____ than the bonds in the starting materials.
reactants, weaker
What property of a molecule is most important in determining its odor?
shape
When _____ is/are dissolved in water, spherical droplets called _____ are formed.
soap; micelles
What type of interaction(s) destabilize a cyclohexane chair conformation that has a bulky substituent in an axial position
steric interactions 1,3,-diaxial interactions
Bromide (Br-) is a ______ nucleophile than fluoride (F-) in water because fluoride will make ______ hydrogen bonds to the solvent.
stronger, stronger
Which product(s) is/are formed when the alkene shown is reacted with O3 followed by Zn reduction?
structure A structure B
Which two carbonyl compounds are obtained after complete oxidative cleavage and reduction of the alkene shown
structure A structure C
A chiral molecule and a stereogenic carbon are not the same thing
true
A particular reaction is found to be bimolecular. This means that
two reactants are involved in the rate-determining step
Phosphate, diphosphate, and triphosphate make good leaving groups in biological substitutions because they are
weak, resonance-stabilized bases
Match each combination of ΔGo and Keq with the preferred direction of reaction at equilibrium
ΔGo < 0; Keq > 1 matches Choice Equilibrium favors products. ΔGo > 0; Keq < 1 matches Choice Equilibrium favors reactants.
What type of arrow is used to indicate a retrosynthetic anaylsis
⇒
