Organic Chemistry II: Chapter 12

In organic chemistry, all reducing agents provide the equivalent of _____ _____ atom(s) to the reaction. a) 2 hydrogen b) 2 oxygen: Reducing agents supply hydrogen, not oxygen. c) 1 oxygen: Reducing agents supply hydrogen, not oxygen. d) 1 hydrogen: Reducing agents supply the equivalent of 2 hydrogen atoms, not 1.

a) 2 hydrogen Reasons: 2 oxygen: Reducing agents supply hydrogen, not oxygen. 1 oxygen: Reducing agents supply hydrogen, not oxygen. 1 hydrogen: Reducing agents supply the equivalent of 2 hydrogen atoms, not 1.

Select all that apply Which of the following options correctly describe the oxidation of primary alcohols? a) A carboxylic acid can be produced by oxidation of a primary alcohol. b) Primary alcohols require different oxidizing conditions than secondary alcohols. c) During oxidation, a primary alcohol will rearrange to produce a more substituted oxidation product. d) Harsher oxidizing conditions will produce a ketone from a primary alcohol. e) Mild oxidizing conditions will result in an aldehyde product.

a) A carboxylic acid can be produced by oxidation of a primary alcohol. e) Mild oxidizing conditions will result in an aldehyde product.

Why can a palladium (Pd) catalyst not be used to reduce an alkyne to an alkene? a) Both π bonds will be reduced. b) The C-C σ bond will react instead of the π bond. c) The alkyne will decompose. d) Pd is unreactive toward triple bonds.

a) Both π bonds will be reduced.

Both KMnO4 and OsO4 are used to effect syn dihydroxylation of an alkene. Match each reagent with the reaction conditions under which it is used. a) KnO4 b) OsO4 i) followed by aqueous NaHSO3 ii) in aqueous OH-

a) KnO4 -- ii) in aqueous OH- b) OsO4 -- i) followed by aqueous NaHSO3 i) followed by aqueous NaHSO3 ii) in aqueous OH-

Select all that apply Which of the following may be components of the Lindlar catalyst? a) Pb(OAc)2 b) quinoline c) Na/NH3 d) Pd/CaCO3 e) Pt

a) Pb(OAc)2 b) quinoline d) Pd/CaCO3

Select all that apply The Lindlar catalyst is composed of Pd on a CaCO3 support. The metal is "poisoned" or made less reactive toward π bonds by the addition of _____ and _____. a) Pb(OAc)2 b) quinoline c) charcoal d) CuCl2

a) Pb(OAc)2 "lead (II) acetate" b) quinoline

Select all that apply Which of the following steps are involved in anti dihydroxylation of an alkene? a) Reaction of an alkene with peroxyacid b) Nucleophilic attack on an epoxide c) Oxidation with H2O2 d) Reaction of an alkene with O3

a) Reaction of an alkene with peroxyacid b) Nucleophilic attack on an epoxide

Select all that apply Which of the following options correctly describe the oxidation of secondary alcohols? a) Secondary alcohols can be oxidized by any Cr(VI) oxidizing agent. b) Secondary alcohols are only oxidized under basic conditions. c) Secondary alcohols are oxidized to form ketones. d) PCC does not oxidize secondary alcohols because it is less reactive than other oxidizing agents.

a) Secondary alcohols can be oxidized by any Cr(VI) oxidizing agent. c) Secondary alcohols are oxidized to form ketones.

Select all that apply Which of the following options correctly describe the addition of H2 to an alkene? a) The product of this reaction is an alkane. b) This reaction is a reduction reaction. c) One hydrogen atom is added to each carbon atom of the double bond. d) Both hydrogen atoms are added to the same carbon of the double bond. e) The reaction involves addition of H- and H+ to the carbon atoms.

a) The product of this reaction is an alkane. b) This reaction is a reduction reaction. c) One hydrogen atom is added to each carbon atom of the double bond.

Select all that apply Which of the following options correctly describe a dihydroxylation reaction? a) The product of this reaction may be called a glycol. b) The product of this reaction is an epoxide. c) This type of reaction always results in syn addition of the OH groups. d) A dihydroxylation reaction is also called a hydration reaction. e) In this reaction an alkene is converted to a diol.

a) The product of this reaction may be called a glycol. e) In this reaction an alkene is converted to a diol.

Select all that apply Which of the following classes of compounds can be produced by oxidation of a primary alcohol? a) aldehyde b) acid anhydride c) ester d) ketone e) carboxylic acid

a) aldehyde e) carboxylic acid

Match each compound correctly to the product obtained on reaction with H2 and a metal catalyst. a) aldehyde b) ketone c) alkene i) alkane ii) primary alcohol iii) secondary alcohol

a) aldehyde -- ii) primary alcohol b) ketone -- iii) secondary alcohol c) alkene -- i) alkane

Oxidation of a secondary alcohol produces a(n) _____. a) ketone b) tertiary alcohol c) carboxylic acid d) aldehyde

a) ketone

Match each type of alkyne to the product(s) produced by oxidative cleavage, a) terminal alkyne b) internal alkyne c) ethyne i) one carboxylic acid and CO2 ii) two carboxylic acids iii) CO2 only

a) terminal alkyne -- i) one carboxylic acid and CO2 b) internal alkyne -- ii) two carboxylic acids c) ethyne -- iii) CO2 only

Reduction of an alkyne with H2 and a Pd catalyst will always produce a(n) _______ as the product because the catalyst is highly reactive toward ______ bonds.

alkane; pi

Select all that apply Which of the following functional groups can be reduced by reaction with metal hydride reagents such as LiAlH4? a) Alcohols b) Alkyl halides c) Epoxides d) Alkanes

b) Alkyl halides c) Epoxides

Select all that apply Which products could be produced by oxidative cleavage of an alkyne? a) ketones b) CO2 c) aldehydes d) carboxylic acids

b) CO2 d) carboxylic acids

Click and drag on elements in order Place the steps involved in catalytic hydrogenation in the correct sequence, starting with the first step at the top of the list. a) The pi bond of the alkene complexes with the metal. b) H2 adsorbs to the catalyst surface. c) Two H2 atoms are transferred sequentially to the pi bond. d) The alkane is released from the catalyst surface.

b) H2 adsorbs to the catalyst surface. a) The pi bond of the alkene complexes with the metal. c) Two H2 atoms are transferred sequentially to the pi bond. d) The alkane is released from the catalyst surface.

Select all that apply Which of the following functional groups can be reduced by reaction with H2 and a metal catalyst? a) alcohol b) aldehyde c) ketone d) alkene e) alkyne

b) aldehyde c) ketone d) alkene e) alkyne

Select all that apply Which of the following types of compounds can be produced by oxidation of an alcohol? a) ether b) aldehyde c) alkyl halide d) carboxylic acid e) ketone

b) aldehyde d) carboxylic acid e) ketone

Oxidative cleavage of an alkene breaks both the σ and the π bonds of the double bond to form two new compounds, each of which contains a(n) _____ group. a) hydroxyl b) carbonyl c) ether d) sulfide

b) carbonyl

Anti dihydroxylation involves two steps, first the formation of a(n) _____ followed by _____ attack under either acidic or basic conditions. a) diol, electrophilic b) epoxide, nucleophilic c) diol, nucleophilic d) epoxide, electrophilic

b) epoxide, nucleophilic

Select all that apply Which of the following sets of reagents will result in syn dihydroxylation of an alkene? a) CrO3 in aqueous acid b) i) OsO4, ii) NaHSO3, H2O c) NaBH4 in CH3OH d) i) mCPBA, ii) OH- e) KMnO4 in aqueous OH-

b) i) OsO4, ii) NaHSO3, H2O e) KMnO4 in aqueous OH-

Reaction of an alkene with H2 to form an alkane is an example of a(n) _____ reaction because there is a(n) _____ in the number of C-H bonds. a) oxidation, increase b) reduction, increase c) oxidation, decrease d) reduction, decrease

b) reduction, increase

Reaction of an alkene with H2 to form an alkane is an example of a(n) _____ reaction because there is a(n) _____ in the number of C-H bonds. a) oxidation, increase b) reduction, increase c) reduction, decrease d) oxidation, decrease

b) reduction, increase

Epoxidation results in syn addition to an alkene. The stereochemistry of the alkene is therefore ______ in the final product. a) inverted b) retained

b) retained

Epoxidation is a reaction in which _____ oxygen atom(s) is/are added across a _____ bond to form an epoxide. a) 1, triple b) 2, double c) 1, double d) 2, triple

c) 1, double

Select all that apply Which of the following options correctly describe an epoxidation reaction? a) The oxygen atom of the epoxide is part of a 5-membered ring system. b) An epoxide is formed when an alkene is reacted with O3. c) An alkene is reacted with a peroxyacid to give an epoxide. d) An oxygen atom is added to each carbon of a double bond in this type of reaction. e) A single oxygen atom is added across the double bond of an alkene in this type of reaction.

c) An alkene is reacted with a peroxyacid to give an epoxide. e) A single oxygen atom is added across the double bond of an alkene in this type of reaction.

Select all that apply Which of the following options correctly describe the mechanism of hydrogenation of an alkene in the presence of a metal catalyst? a) The H atoms are transferred from the catalyst to the alkene in a single step. b) The H2 molecule is cleaved to form two H atoms, which can react with the alkene. c) H2 molecules are adsorbed onto the surface of the catalyst. d) The catalyst complexes to the π bond of the alkene. e) The catalyst, the alkene, and the H2 must be in the same phase for the reaction to occur.

c) H2 molecules are adsorbed onto the surface of the catalyst. b) The H2 molecule is cleaved to form two H atoms, which can react with the alkene. d) The catalyst complexes to the π bond of the alkene.

Select all that apply Which of the following compounds could be produced by reacting an alkene with O3 followed by either Zn or CH3SCH3? a) Carboxylic acid b) Alcohol c) Ketone d) Aldehyde

c) Ketone d) Aldehyde

A dihydroxylation reaction is one in which two _____ groups are added to adjacent carbon atoms of a C=C double bond. The product of the reaction is called a(n) _____. a) OH, 1,3-diol b) C=O, 1,2-diol c) OH, 1,2-diol d) C=O, 1,3-diol

c) OH, 1,2-diol

Select all that apply Which of the following options correctly describe the relationship between the geometry of the starting alkene and the stereochemistry of the epoxide that it forms? a) A trans alkene undergoes anti addition, whereas a cis alkene undergoes syn addition when forming an epoxide. b) A cis alkene will give rise to a trans epoxide, whereas a trans alkene gives rise to a cis epoxide. c) The substituents in a cis alkene will still be cis in the epoxide. d) The geometry of the alkene is retained in the epoxide due to syn addition.

c) The substituents in a cis alkene will still be cis in the epoxide. d) The geometry of the alkene is retained in the epoxide due to syn addition.

Organic oxidation often results in the replacement of C-H bonds with C-O bonds. Alcohols already contain a C-O bond, so oxidation of these compounds gives a product that contains a(n) _____ functional group. a) alkene b) ester c) carbonyl d) carboxyl

c) carbonyl

Which reagent will facilitate anti addition of H2 across a triple bond to give a trans alkene? a) aqueous NH4Cl b) H2 on Pt c) NaBH4 d) Na in liquid NH3

d) Na in liquid NH3

Which of the following options correctly describe all reducing agents in organic chemistry? a) They bond to oxygen, thus reducing the number of C-O bonds in the compound. b) They provide a source of H2 in the reaction. c) They provide a source of electrons for electron transfer. d) They provide the equivalent of 2 H atoms to the reaction.

d) They provide the equivalent of 2 H atoms to the reaction.

Reduction of an alkyne with Na metal in liquid NH3 results in _____ addition of the elements of H2 across the triple bond and a _____ alkene is produced. a) anti, cis b) syn, trans c) syn, cis d) anti, trans

d) anti, trans

Certain compounds containing ______ C-X σ bonds may be reduced with reagents such as LiAlH4 in a nucleophilic ______ reaction. a) polar, addition b) nonpolar, substitution c) nonpolar, addition d) polar, substitution

d) polar, substitution