Organic Chemistry 2 Chapter 19 ALL Questions (all 19.1 and 19.2 D Quiz 1/1)

B. a hemiacetal

A compound with an OH and OR group attached to the same carbon is known as A. an acetal B. a hemiacetal C. a hydrate D. a vicinal hydrate E. none of these

C. III

A compound with formula C5H10O shows only two singlets, in its 1H NMR spectrum. Which one of the following is a possible structure for the compound? A. I B. IV C. III D. II E. V

A. I

Compound A on ozonolysis yields the following two products. What is the structure of compound A? (1. O3 2. (CH3)2S A. I B. II C. III D. IV

C. acetone

Name the aldehyde or ketone that is found in nail polish remover. A. diethyl ether B. ethanol C. acetone D. formaldehyde E. 2-butanone

E. 2-hexanone

Predict the product for the following reaction (2-hexanol, Na2Cr2O7, H2SO4, H2O) A. hexanoic acid B. 1-hexanol C. 2-chlorohexane D. hexanal E. 2-hexanone

E. II

Predict the product for the following reaction sequence. ((CH3CH2)2NH, H2SO4) A. IV B. I C. V D. III E. II

A. III

Predict the product for the following reaction. (AlCl3) A. III B. II C. V D. I E. IV

C. (R)-6-bromo-2-heptanone

What is the IUPAC name for the following compound? A. (R)-2-bromo-6-heptanone B. (R)-6-bromo-2-heptanal C. (R)-6-bromo-2-heptanone D. (S)-6-bromo-2-heptanone E. (S)-6-bromo-2-heptanal

C. hexanal

Predict the product for the following reaction. (1-hexanol, 1. DMSO, (COCl)2 2. Et3N) A. 1-hexanol B. 2-hexanone C. hexanal D. 2-chlorohexane E. hexanoic acid

E. V

Predict the product for the following reaction. (1. excess O3 2. (CH3)2S) A. 1 B. III C. IV D. II E. V

B. 2-hexanone

Predict the product for the following reaction. (2-hexanol, PCC, CH2Cl2) A. hexanoic acid B. 2-hexanone C. 1-hexanol D. hexanal E. 2-chlorohexane

B. III

Predict the product of the following reaction sequence. (NaCN, HCN, 1. LiALH4 2. H2O) A. I B. III C. II D. IV E. V

D. CH3CH2MgBr/ether

Provide the reagents necessary for the following conversion. A. 1. H3O+ 2. CH3CH2MgBr/ether B. 1. CH3CH2MgBr/ether 2. H3O+, heat C. 1. NaBH4/CH3OH 2. CH3CH2MgBr D. CH3CH2MgBr/ether

A. 1. NH2NH2/H+ 2. KOH/H2O/heat

Provide the reagents necessary to carry out the following conversion. A. 1. NH2NH2/H+ 2. KOH/H2O/heat B. NaBH4/CH3OH C. 1. LiAlH4 2. H2O D. H2/Ni

C. V

Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid. A. I B. II C. V D. IV E. III

C. Ph3P=CHCH2CH2CH3

Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction. A. Ph3P=CH2 B. Ph3P=CHCH2(CH3)2 C. Ph3P=CHCH2CH2CH3 D. Ph3P=CHCH2CH3 E. Ph3P=CH(CH2CH3)2

E. I > III > II > IV > V

Rank the compounds in decreasing order (most to least) of reactivity towards a nucleophilic addition reaction. A. III > I > V > IV > II B. V > IV> II >III> I C. I > II > III > IV > V D. II > IV > V > III > I E. I > III > II > IV > V

C. 2,2-dimethyl-3-pentanone

The 13 C NMR spectrum of a compound with formula C7H14O shows five signals. Which one of the following is a possible structure for this compound? A. 2-heptanone B. 3-heptanone C. 2,2-dimethyl-3-pentanone D. 2,4-dimethyl-3-pentanone E. none of these

B. III

Predict the product for the following reaction. (excess CH3CH2OH, H2SO4) A. IV B. III C. II D. I E. V

E. 3-phenylpropanal

What is the IUPAC name for the following compound? A. 4-benzylbutanal B. 4-phenylbutanal C. 2-benzylethanal D. 3-benzylpropanal E. 3-phenylpropanal

E. II

What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal? A. III B. V C. IV D. I E. II

C. a hydrate

A compound with two OH groups attached to the same carbon is known as A. an acetal B. a hemiacetal C. a hydrate D. a vicinal hydrate E. none of these

B. 3-methyloctanal

Predict the product for the following reaction (3-methyl-1-octanol, PPC, CH2Cl2) A. 3-methyloctanone B. 3-methyloctanal C. 2-methyloctanone D. 2-methyloctanal E. 2-methyloctanoic acid

A. II

Predict the product for the following reaction sequence. (PCC, (CH3)2NH, H2SO4) A. II B. III C. I D. IV E. V

D. IV

Predict the product for the following reaction sequence. (Ph3P, CH3CH2CH2CH2Li, ether, CH3CCH2CH3) A. III B. I C. V D. IV E. II

C. IV

Predict the product for the following reaction. (+NH, CrO3, Cl-, CH2Cl2) A. V B. I C. IV D. II E. III

E. 3-methyloctanal

Predict the product for the following reaction. (3-methyl-1-octanol, 1. DMSO, (COCl)2 2. Et3N) A. 2-methyloctanol B. 2-methyloctanone C. 2-methyloctanoic acid D. 3-methyloctanone E. 3-methyloctanal

A. 3-methyloctanal

Predict the product for the following reaction. (3-methyl-1-octanol, DMP, CH2Cl2) A. 3-methyloctanal B. 2-methyloctanone C. 2-methyloctanal D. 3-methyloctanone E. 2-methyloctanoic acid

C. IV

Predict the product for the following reaction. (H2O/H2SO4, HgSO4) A. I B. II C. IV D. V E. III

A. I

Predict the product for the following reaction. (H2SO4) A. I B. II C. III D. V E. IV

D. IV

Predict the product for the following reaction. (NH2OH, H2SO4) A. II B. V C. I D. IV E. III

D. IV

Predict the product for the following reaction. (Na2Cr2O7, H2SO4, H2O) A. V B. III C. II D. IV E. I

B. II

Predict the product for the following reaction. (PCC, excess, CH2Cl2) A. V B. II C. IV D. I E. III

A. I

Predict the product for the following reaction. (excess 1. NH2NH2/H+ 2. KOH/H2O/heat) A. I B. III C. II D. V E. IV

C. III

Predict the product for the following reaction. (excess CH3CH2OH, H2SO4) A. I B. II C. III D. IV E. none of these

A. I

Predict the product for the following reaction. (excess H2O, H2SO4) A. I B. II C. III D. IV E. none of these

D. I

Predict the product for the following reaction. (excess, 1. NH2NH2/H+ 2. KOH/H2O/heat) A. III B. II C. IV D. I E. V

B. II

Predict the product of the following reaction sequence. (NaCN, HCN) A. I B. II C. III D. IV E.V

D. III

Predict the product of the following reaction. (CH3COOH) A. I B. IV C. II D. III

A. II

Predict the product of the following reaction. (CH3COOH) A. II B. I C. III D. V E. IV

D. IV

Predict the product of the following reaction. (NH2OH, H2SO4) A. V B. II C. I D. IV E. III

E. II

Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst. A. V B. I C. III D. IV E. II

A. III

Predict the products for the following reaction. (H3O+, heat) A. I B. III C. V D. II E. IV

A. 3-methylhexane

Provide the product for the following reaction. (1. NH2NH2/H+ 2. KOH/H2O/heat) A. 3-methylhexane B. 3-methyl-4-hexanol C. 3-methyl-4-hexene D. 4-methyl-2-hexene E. 3-methyl-3-hexene

B. V

Provide the product of the following reaction. (propanol, H2SO4, Raney, Ni) A. III B. V C. I D. II E. IV

E. B & C

The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at 9.2 ppm. Which one of the following is a possible structure for the product? A. 2-methyl-3-hexanone B. 2-methylhexanal C. 2,2-dimethylpentanal D. 2,2-dimethyl-3-pentanone E. B & C

C. 7-methyl-4-octane

What is the IUPAC name for the following compound? A. 1,1-dimethyl-4-heptanone B. isobutyl propyl ketone C. 7-methyl-4-octane D. 2-methyl-5-heptanone E. 6-isopropyl-4-octane

B. 2,5-dimethylhexanal

What is the IUPAC name for the following compound? A. 2,5-dimethyl-6-hexanal B. 2,5-dimethylhexanal C. 1,4-dimethylpentanal D. 1,4-dimethylhexanal E. none of these

B. 4,4-dimethylcycloheptanone

What is the IUPAC name for the following compound? A. 5,5-dimethyl-2-heptanone B. 4,4-dimethylcycloheptanone C. 1,1-dimethyl-4-cycloheptanone D. 5,5-dimethylcycloheptanone E. 3,3-dimethylcycloheptanone

C. 4-(1-methylcyclohexyl)-2-butanone

What is the IUPAC name for the following compound? A. 5-cyclohexyl-2-hexanone B. 5-cyclohexyl-2-hexanal C. 4-(1-methylcyclohexyl)-2-butanone D. 5-(1-methylcyclohexyl)-2-pentanone E. 5-cyclohexyl-5-methyl-2-pentanone

D. H > t-butyl > phenyl > methyl

What is the correct order of the migration rate for the following groups in the Baeyer-Villiger oxidation reaction? A. methyl > t-butyl > phenyl > H B. phenyl > methyl > t-butyl > H C. H > phenyl > methyl > t-butyl D. H > t-butyl > phenyl > methyl E. phenyl > t- butyl > methyl > H

C. III

What is the structure for 5-hydroxy-2-phenyl-3-hexanone? A. I B. V C. III D. II E. IV

A. I

What would be the product of the following reaction? (1. LiAlH4 2. H2O) A. I B. IV C. III D. II E. V

E. I

What would be the product of the following reaction? (NaBH4/CH3OH) A. II B. IV C. V D. III E. I

C. 2-pentanone and 1-bromopropane/PPh3

Which of the following is the best choice to prepare the following alkene using the Wittig reaction? A. ethanal and 2-bromopentane/PPh3 B. propanal and 2-bromopentane/PPh3 C. 2-pentanone and 1-bromopropane/PPh3 D. 2-pentanone and 2-bromopropane/PPh3 E. butanal and 2-bromopentane/PPh3

B. a proton transfer followed by a nucleophilic attack

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under acidic conditions? A. proton transfer is not required B. a nucleophilic attack followed by a proton transfer C. a proton transfer followed by a nucleophilic attack D. nucleophilic attack is the only step

A. a nucleophilic attack followed by a proton transfer

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under basic conditions? A. a nucleophilic attack followed by a proton transfer B. proton transfer is not required C. nucleophilic attack is the only step D. a proton transfer followed by a nucleophilic attack