Question 1

The positively polarized carbon atom of a carbonyl group acts as:

Accepted Answer

A)  an electrophile and a Lewis base. 
B)  a nucleophile and a Lewis base. 
C)  an electrophile and a Lewis acid. 
D)  a nucleophile and a Lewis acid. 
E)  both a Lewis acid and a Lewis base. 
A)  an electrophile and a Lewis base. 
B)  a nucleophile and a Lewis base. 
C)  an electrophile and a Lewis acid. 
D)  a nucleophile and a Lewis acid. 
E)  both a Lewis acid and a Lewis base.

Question 2

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 3

What reagents can be used to convert 1-hexyne into 2-hexanone?

Accepted Answer

A)  1. Sia2BH; 2. H2O2, NaOH 
B)  Hg2+, H2SO4, H2O 
C)  1. O3; 2. (CH3)2S 
D)  1. CH3MgBr; 2. CO2 
E)  1. H2, Ni; 2. Na2Cr2O7, H2SO4 
A)  1. Sia2BH; 2. H2O2, NaOH 
B)  Hg2+, H2SO4, H2O 
C)  1. O3; 2. (CH3)2S 
D)  1. CH3MgBr; 2. CO2 
E)  1. H2, Ni; 2. Na2Cr2O7, H2SO4

Question 4

Which series of reactions described below, if any, will result in the formation of 2-methylpentan-3-one starting with 1-propanol?

Accepted Answer

A)  1. (CH3)2CHMgBr/ diethyl ether 2. dilute H3O+
3) PCC 
B)  1. Na2Cr2O7/H2SO4 and heat 2. SOCl2
3) 2 (CH3)2CHMgBr/ diethyl ether
4) H3O+ 
C)  1. Na2Cr2O7/H2SO4 and heat 2. (CH3)2CHMgBr/ diethyl ether
3) dilute H3O+
4) LiAlH4 
D)  1. PCC 2. (CH3)2CHLi/ diethyl ether
3) dilute H3O+
4) Na2Cr2O7/H2SO4 and heat 
E)  none of the above 
A)  1. (CH3)2CHMgBr/ diethyl ether 2. dilute H3O+
3) PCC 
B)  1. Na2Cr2O7/H2SO4 and heat 2. SOCl2
3) 2 (CH3)2CHMgBr/ diethyl ether
4) H3O+ 
C)  1. Na2Cr2O7/H2SO4 and heat 2. (CH3)2CHMgBr/ diethyl ether
3) dilute H3O+
4) LiAlH4 
D)  1. PCC 2. (CH3)2CHLi/ diethyl ether
3) dilute H3O+
4) Na2Cr2O7/H2SO4 and heat 
E)  none of the above

Question 5

What is the correct IUPAC name for the following compound?

Accepted Answer

A)  2-oxocyclohex-3-ene carbaldehyde 
B)  5-formylcyclohex-2-enone 
C)  2-formylcyclohex-5-enone 
D)  3-oxocyclohex-4-enal 
A)  2-oxocyclohex-3-ene carbaldehyde 
B)  5-formylcyclohex-2-enone 
C)  2-formylcyclohex-5-enone 
D)  3-oxocyclohex-4-enal

Question 6

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 7

Which of the following describes a synthesis of an aldehyde?

Accepted Answer

A)  hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst 
B)  reaction of a primary alcohol with Na2Cr2O7 
C)  reaction of a ketone with ozone 
D)  treatment of an alkene with Sia2BH 
E)  none of the above 
A)  hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst 
B)  reaction of a primary alcohol with Na2Cr2O7 
C)  reaction of a ketone with ozone 
D)  treatment of an alkene with Sia2BH 
E)  none of the above

Question 8

Provide the necessary reagents to complete the following transformation.

Accepted Answer

The answer of Provide the necessary reagents to complete the...

Question 9

Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.

Accepted Answer

1. CH₃CH₂CH₂C

Question 10

Name the compound generated when 1-methylcyclohexene is subjected to O3 followed by dimethyl sulfide.

Accepted Answer

Question 11

When H2NCH2CH2CH2CH2COCH3 is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C6H11N. Provide the structure of this product.

Accepted Answer

Question 12

Provide the major organic product which results in the reaction shown below.

Accepted Answer

The answer of Provide the major organic product which results...

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 14

What organic compound is generated when PhCOCl is treated with (CH3CH2CH2)2CuLi?

Accepted Answer

Question 15

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH3COCH2CH3, H2CO, Cl3CCHO, and CH3CH2CHO.

Accepted Answer

CH₃COCH₂CH₃ <

Question 16

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents:
1. n-BuLi 
2. (CH3)3CCH2CH2CH2I
 3. HgCl2, H3O+?

Accepted Answer

Question 17

Provide the structure of cyclohexanone oxime.

Accepted Answer

The answer of Provide the structure of cyclohexanone oxime....

Question 18

The strongest absorptions in the UV spectra of aldehydes and ketones are ones which result from ________ electronic transitions.

Accepted Answer

A)  σ to σ* 
B)  σ to π* 
C)  n to π* 
D)  π to π* 
E)  π to σ* 
A)  σ to σ* 
B)  σ to π* 
C)  n to π* 
D)  π to π* 
E)  π to σ*

Question 19

Trioxane is a cyclic trimer of formaldehyde that can be converted to formaldehyde upon heating. Show this reaction.

Accepted Answer

The answer of Trioxane is a cyclic trimer of formaldehyde...

Question 20

Provide the structure of the major organic product which results when benzaldehyde reacts with hydroxylamine in the presence of acid.

Accepted Answer

The answer of Provide the structure of the major organic...

Exam 18: Ketones and Aldehydes

The positively polarized carbon atom of a carbonyl group acts as:

Provide the major organic product of the reaction shown below.

What reagents can be used to convert 1-hexyne into 2-hexanone?

Which series of reactions described below, if any, will result in the formation of 2-methylpentan-3-one starting with 1-propanol?

What is the correct IUPAC name for the following compound?

Provide the major organic product of the reaction shown below.

Which of the following describes a synthesis of an aldehyde?

Provide the necessary reagents to complete the following transformation.

Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.

Name the compound generated when 1-methylcyclohexene is subjected to O3 followed by dimethyl sulfide.

When H2NCH2CH2CH2CH2COCH3 is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C6H11N. Provide the structure of this product.

Provide the major organic product which results in the reaction shown below.

Provide the major organic product of the following reaction.

What organic compound is generated when PhCOCl is treated with (CH3CH2CH2)2CuLi?

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH3COCH2CH3, H2CO, Cl3CCHO, and CH3CH2CHO.

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents: 1. n-BuLi 2. (CH3)3CCH2CH2CH2I 3. HgCl2, H3O+?

Provide the structure of cyclohexanone oxime.

The strongest absorptions in the UV spectra of aldehydes and ketones are ones which result from ________ electronic transitions.

Trioxane is a cyclic trimer of formaldehyde that can be converted to formaldehyde upon heating. Show this reaction.

Provide the structure of the major organic product which results when benzaldehyde reacts with hydroxylamine in the presence of acid.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Name the compound generated when 1-methylcyclohexene is subjected to O₃ followed by dimethyl sulfide.

When H₂NCH₂CH₂CH₂CH₂COCH₃ is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C₆H₁₁N. Provide the structure of this product.

What organic compound is generated when PhCOCl is treated with (CH₃CH₂CH₂)₂CuLi?

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH₃COCH₂CH₃, H₂CO, Cl₃CCHO, and CH₃CH₂CHO.

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents: 1. n-BuLi 2. (CH₃)₃CCH₂CH₂CH₂I 3. HgCl₂, H₃O⁺?