CHEM 232 UNIT 3 EXAM QUESTIONS ANSWERED CORRECTLY LATEST UPDATE 2026

CHEM 232 UNIT 3 EXAM QUESTIONS ANSWERED CORRECTLY LATEST UPDATE 2026 Alkoxide - Answers Deprotonated alcohol. increases - Answers Increased beta-branching of an alcohol __________ the pKa. decreases - Answers Increased alpha-branching of an alcohol __________ the pKa. Oxonium - Answers R3O+ Activation - Answers Protonating alcohols to generate oxonium ions to act as great leaving groups, since neutral oxygens are the worst leaving groups and water is the best. Amphoteric - Answers A species that can act as either an acid or a base (ex. alcohols). Sn2 - Answers Methyl and primary alkyl halides can be synthesized into alcohol using the ______ rxn mechanism. Sn1/E1 - Answers Tertiary alkyl halides utilize ________ because a strong base cannot be used. SnAc - Answers Mechanism in which there is a substitution at a carbonyl functional group using NaOH. Acyl - Answers Word that refers to a substitution at a carbonyl. alpha - Answers Nucleophiles are attracted to the partial positive charge on the ______ carbon. pi bond - Answers What is the new LUMO in SnAc rxn? 2 - Answers How many steps are in the SnAc rxn? tetrahedral - Answers SnAc mechanism has an intermediate with _______________ geometry. Nu attacks - Answers Step 1 of SnAc. Regenerate carbonyl bond/LG leaves - Answers Step 2 of SnAc. nucleophile - Answers The HOMO is on the _____________. lone pair in sp3 orbital - Answers Where is the HOMO on a negatively charged oxygen atom? electrophile - Answers The LUMO is on the _____________. carbonyl pi bond - Answers Where is the LUMO on an ester? Sn1/E1 - Answers H2O leaving group at 2º C will always be (Sn1/E1 or Sn2). Dehydration - Answers A ____________ reaction allows us to target E1 over Sn1; utilizes a non-nucleophilic acid to protonate the OH and requires an input of heat bc endothermic. H2O is a fantastic leaving group so it will leave and form a stable alkene. Follows Zaitzev's rule. 3º 2º - Answers For dehydration rxns, list most reactive starting material least reactive. 1º - Answers __º alcohols are too unstable to form carbocations; reverts back to E2 instead of dehydration E1. If no strong base is present, the reaction can be compensated with a very high temperature. Neopentyl alcohol - Answers Similar to a tert-butyl alcohol, but cannot perform Sn1/E1, Sn2, or E2. Must rearrange by way of a concerted alkyl shift. beta-C has too many groups attached to it (4º) even though the alpha-C is only 1º. Still too hindered though. nucleophilic - Answers Acids that are HX in which X = Cl, Br, or I are said to be ____________. Sn1 - Answers Activation of a 2º alcohol requires what kind of reaction? dehydration reaction - Answers An E1 reaction in which an alcohol is turned into an alkene through the creation of a water molecule. The OH group in the base deprotonates the hydroxide group in the alcohol, making it a better leaving group. electrophile - Answers PBr3 is a great electrophile, which drives the activation of alcohols through the use of phosphorus tribromide or phosphorus trichloride. Sn2 - Answers Activation of alcohols using PBr3 or PCl3 occurs through an ______ reaction. Pyridine - Answers What kind of solvent is used in the activation of alcohols using thionyl chloride (SOCl2)? Pyridine - Answers A weak base that is used in the activation of alcohols using thionyl chloride; acts as a base during the acid/base neutralization step that occurs after SnAc. lower - Answers Ethers have ________ melting and boiling points than corresponding alcohols. This is due to the absence of intramolecular hydrogen bonding. inert - Answers Ethers lack protons, making them _______ towards strong bases. cations - Answers In contrast to polar protics that solvate anything that is charged, ethers only solvate _________. Ionophore - Answers A class of membrane transport proteins. Small, hydrophobic molecules that increase membrane permeability to certain ions. An example of an ether in a living system. Monensin A - Answers An ionophore that transports sodium ions across a phospholipid bilayer. Wraps around cations. Willamson Ether Synthesis - Answers An organic reaction involving a methyl or primary unhindered alkyl halide and an alkoxide undergoing an Sn2 rxn that results in the formation of an ether. faster - Answers Intramolecular reactions are (slower/faster) than intermolecular reactions. ring - Answers Intramolecular Williamson Ether Synthesis reactions turn an alkane into a _______. elimination - Answers The input of heat into a reaction promotes ___________. Symmetric Ether Synthesis - Answers A reaction involving 2 alcohols of the same reactivity and beta branching that produces a symmetrical ether. Sn1 - Answers Primary and secondary alcohols undergo _____ when synthesizing an ether. non-nucleophilic acid - Answers Strong acids H2SO4, H3PO4, SO3OH- that all use elimination reactions. nucleophilic acid - Answers HBr, HI, HCl that all use substitution reactions. ether cleavage using a nucleophilic acid - Answers A reaction that involves the use of a nucleophilic acid (HX) to open an ether ring. X attaches to a carbon adjacent to the oxygen and forms a carbocation. The second step involves the substitution of X from excess HX for the water molecule in the ether. ether cleavage using a non-nucleophilic acid - Answers A reaction that involves the use of a non-nucleophilic acid (ex. H2SO4) to open an ether ring. The least substituted group connected to the oxygen acts as the leaving group and forms a carbocation and then an acid/base step neutralizes it. Another product that is formed is when the more substituted group acts as the leaving group. epoxide formation - Answers Intramolecular Willamson Ether Synthesis; a halohydrin is converted to an epoxide. The LG leaves and the proton attached to the oxygen is stolen by an OH nucleophile to form water, causing the 3 sigma bonds to form a triangle with the lone oxygen standing as one of the points. epoxide opening - Answers An SN2 reaction in which a relatively strong nucleophile attacks one of the central carbons in an epoxide and forms a new sigma bond. An acidic workup then occurs and adds a proton to the oxygen. hydride reagent - Answers A reagent that acts as the hydride ion would if it were nucleophilic. EX: LiAlH4 (general form is H-Nu). organometallic reagent - Answers A reagent that contains a carbon-metallic bond; includes Grignard reagents, organolithium reagents, and terminal alkynes. General form is C-Nu). Grignard reagent - Answers An alkyl magnesium halide that is used to make carbon-carbon bonds. General form is RMgX (usually Br). Organolithium reagent - Answers Any organometallic compound having the form R-Li. terminal alkyne - Answers An alkyne in whose molecule there is at least one hydrogen atom bonded to a triply bonded carbon atom. Function of diethyl ether in an LiAl H4 epoxide expansion rxn. - Answers Dissociates Li from Al and allows it to float around in solution. -ane - Answers Suffix when naming an alkane. -ol - Answers Suffix when naming an alcohol. loses - Answers Something that is being oxidized (gains/loses) electrons. takes - Answers Oxidant (receives/donates) electrons. gains - Answers Something that is reduced (gains/loses) electrons. donates - Answers Reductant (donates/receives) electrons.