Question 1

4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HCl (gas) in diethyl ether at 5^oC. What is the main product formed? A) I B) II C) III D) IV

Accepted Answer

The reaction involves acid-catalyzed dehydration of the alcohol, resulting in the formation of a carbocation intermediate. This intermediate can then undergo two pathways: (I) protonation at the hydroxyl group followed by loss of a water molecule to give a secondary carbocation, which then undergoes hydride shift and subsequent deprotonation to yield the major product as shown in option B. (II) Alternatively, the carbocation can undergo a methyl shift to give a tertiary carbocation that undergoes deprotonation to give a minor product (option A). The other two options (C and D) involve unlikely rearrangements and are not observed under normal reaction conditions.

Question 2

Arrange the compounds in the order of increasing acidity (least first).&#10; &#10;A) III, I, II, IV&#10;B) I, III, IV, II&#10;C) II, III, I, IV&#10;D) II, I, III, IV

Accepted Answer

To determine acidity we look at the stability of the conjugate base. The more stable the conjugate base, the more acidic the compound.

II (methane) has no acidic hydrogen atoms and therefore it is not acidic.

III (ethanol) has a less stable conjugate base than I because it has a greater tendency to donate its proton due to the electron-donating nature of the ethyl group.

I (acetic acid) has a more stable conjugate base than III because it has a greater tendency to keep its proton due to the electron-withdrawing nature of the carbonyl group.

IV (acetone) has the most stable conjugate base due to the resonance stabilization provided by the carbonyl group. Therefore, it is the most acidic.

So the order is: II, III, I, IV

Question 3

2-(1-hydroxyprop-2-yl) cyclopentanol reacts with a mixture of potassium dichromate in concentrated sulfuric acid at room temperature. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)

A)I
B)II
C)III
D)IV

Accepted Answer

2-(1-hydroxyprop-2-yl) cyclopentanol undergoes oxidation with potassium dichromate in concentrated sulfuric acid to form product IV, which is 2-cyclopentylidene-1-hydroxypropan-1-one. This is because the secondary alcohol functional group is oxidized to a ketone functional group under these conditions.

Question 4

Which are the best conditions for the preparation of 1-chloro-2-methylpropane starting from 2-methyl-1-propanol?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Option B involves the use of concentrated hydrochloric acid as the reagent and zinc chloride as the catalyst. This is the most commonly used method for the preparation of 1-chloro-2-methylpropane from 2-methyl-1-propanol as it gives a high yield of the desired product. Option A uses acyl chloride as the reagent, which is not suitable for this preparation. Option C uses sodium hypochlorite as the reagent, which is not effective for the preparation of this compound. Option D uses sulphuric acid, which can cause the formation of unwanted by-products.

Question 5

Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate the hydrophobic surface of the non-polar part of the molecules)&#10; &#10;A) II, III, I, IV&#10;B) I, II, III, IV&#10;C) IV, II, III, I&#10;D) II, IV, III, I

Accepted Answer

Compound I has a very polar functional group (carboxylic acid) that can easily interact with water molecules via hydrogen bonding, making it the most soluble compound. Compound II has a hydrophobic non-polar ring that reduces its solubility in water. Compound III has a more polar functional group (amide) than II, making it more soluble than II but less soluble than I. Compound IV has a very long hydrophobic alkyl chain, which greatly reduces its solubility in water, making it the least soluble compound. Therefore, the order of increasing solubility in water is I > III > II > IV, and the best choice is B.

Question 6

Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate the hydrophobic surface of the non-polar part of the molecules)&#10; &#10;A) III, IV, II, I&#10;B) II, III, IV, I&#10;C) IV, III, II, I&#10;D) III, IV, I, II

Accepted Answer

The solubility of organic compounds in water depends on their ability to form hydrogen bonds with water molecules. Compounds with polar groups such as OH, NH, and COOH are soluble in water due to the formation of hydrogen bonds with water molecules. On the other hand, compounds with nonpolar groups such as alkyl chains are insoluble in water. To estimate the hydrophobicity of the non-polar part of the molecules, we can look at the length of the alkyl chains and the presence of functional groups that can interact with water molecules.

III has a shorter alkyl chain compared to IV, and it also has a polar amide functional group that can interact with water molecules, so it is the most soluble in water. IV has a longer alkyl chain and no polar functional groups, so it is less soluble than III. II has a shorter alkyl chain compared to IV, but it has no polar functional groups, so it is less soluble than III and IV. I has a longer alkyl chain than IV, and it also has a nonpolar aromatic ring that can interact with water molecules through pi-stacking, so it is the least soluble in water among the four compounds.

Therefore, the correct order of increasing solubility in water is IV, III, II, I, and the best choice is C.

Question 7

4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HBr (gas) in dioxane under pressure at 125^oC. What is the main product formed? A) I B) II C) III D) IV

Accepted Answer

The answer of 4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HBr (gas) in dioxane...

Question 8

Which of the molecules are primary alcohols?&#10; &#10;A) III, II&#10;B) IV, I&#10;C) II, III&#10;D) I, II

Accepted Answer

The answer of Which of the molecules are primary alcohols?&#10;...

Question 9

Which is the product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The product of the given reaction is III, which is sulfuric acid (H2SO4). It is formed by the reaction of sulfur trioxide (SO3) with water (H2O). Option A, Iodine (I2), is not involved in the given reaction. Option B, Hydrogen gas (H2), is not formed in the given reaction. Option D, Iron (III) oxide (Fe2O3), is also not formed in the given reaction.

Question 10

2-(1-hydroxyprop-2-yl) cyclopentanol reacts with a mixture of potassium dichromate in concentrated sulfuric acid at room temperature. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)

A)I
B)II
C)III
D)IV

Accepted Answer

The given compound can undergo oxidation on the hydroxyl group and/or the isopropyl group. Pyridinium chlorochromate (PCC) is a mild oxidizing agent that selectively oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. In this case, the hydroxyl group is a primary alcohol so it will be oxidized to an aldehyde. The isopropyl group does not undergo oxidation with PCC.
 
Therefore, the product formed will be III, 2-(1-formylprop-2-yl) cyclopentanol.

Question 11

Which reagents do not perform the following conversion?&#10; &#10;A) I, II&#10;B) II, III&#10;C) II, IV&#10;D) I, III

Accepted Answer

The answer of Which reagents do not perform the following...

Question 12

Which alcohol will form the most stable carbocation when treated with a strong mineral acid?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which alcohol will form the most stable...

Question 13

Which is the product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the product of the following...

Question 14

Which is the major product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

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The answer of Which is the major product of the...

Question 15

Arrange the compounds in the order of increasing solubility in water (least soluble first).&#10; &#10;A) I, III, II, IV&#10;B) III, I, IV, II&#10;C) I, IV, II, III&#10;D) IV, I, III, II

Accepted Answer

The answer of Arrange the compounds in the order of...

Question 16

Arrange the following in order of increasing rate of reactivity with HCl (least first).&#10; &#10;A) I, II, IV, III&#10;B) II, I, III, IV&#10;C) IV, III, I, II&#10;D) III, II, IV, I

Accepted Answer

The answer of Arrange the following in order of increasing...

Question 17

Which molecules are secondary alcohols?&#10; &#10;A) I, III&#10;B) II, III&#10;C) III, IV&#10;D) I, IV

Accepted Answer

The answer of Which molecules are secondary alcohols?&#10; &#10;A) I,...

Question 18

Which is the IUPAC name for the following structure?&#10; &#10;A) cyclohexenol&#10;B) 3-cyclohexen-1-ol&#10;C) 1-cyclohexen-4-ol&#10;D) 4-cyclohexenol

Accepted Answer

The answer of Which is the IUPAC name for the...

Question 19

The alcohol shown below reacts with thionyl chloride in pyridine. Which organic product is formed?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of The alcohol shown below reacts with thionyl...

Question 20

Which is the best method for making the following conversion?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

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The answer of Which is the best method for making...

Question 21

Arrange the compounds in the order of increasing acidity (least acidic first).&#10; &#10;A) II, III, IV, I&#10;B) I, III, IV, II&#10;C) III, IV, II, I&#10;D) IV, II, III, I

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The answer of Arrange the compounds in the order of...

Question 22

The major product of the following reaction is,&#10;

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The answer of The major product of the following reaction...

Question 23

Arrange the compounds in the order of increasing boiling point (lowest first).&#10; &#10;A) II, I, III, IV&#10;B) I, IV, II, III&#10;C) IV, I, III, II&#10;D) I, IV, III, II

Accepted Answer

The answer of Arrange the compounds in the order of...

Question 24

Arrange the compounds in the order of increasing acidity (least first).&#10; &#10;A) II, I, III, IV&#10;B) I, IV, II, III&#10;C) III, II, I, IV&#10;D) II, I, IV, III

Accepted Answer

The answer of Arrange the compounds in the order of...

Question 25

Classify the following reaction:&#10; &#10;A) oxidation&#10;B) reduction&#10;C) neither&#10;D) both

Accepted Answer

The answer of Classify the following reaction:&#10; &#10;A) oxidation&#10;B) reduction&#10;C)...

Question 26

The alkene shown below reacts with meta-chloroperbenzoic acid (MCPBA) in tetrahydrofuran. Which of the four formulas correctly describe the reaction products?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of The alkene shown below reacts with meta-chloroperbenzoic...

Question 27

The major product of the following reaction is,&#10;

Accepted Answer

The answer of The major product of the following reaction...

Question 28

Which is the major product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the major product of the...

Question 29

Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the major product from the...

Question 30

The reagent needed to complete the following reaction is,&#10;

Accepted Answer

The answer of The reagent needed to complete the following...

Question 31

The reagent needed to complete the following reaction is,&#10;

Accepted Answer

The answer of The reagent needed to complete the following...

Question 32

Which is the major product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the major product of the...

Question 33

Classify the following transformation of a disulfide to two sulfides. How can that transformation be brought about?&#10; &#10;A) oxidation&#10;B) reduction&#10;C) neither&#10;D) both

Accepted Answer

The answer of Classify the following transformation of a disulfide...

Question 34

Which is the major product of the following reaction?&#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the major product of the...

Question 35

Arrange the following in order of increasing ability to hydrogen bond (lowest first).&#10; &#10;A) I, II, III, IV&#10;B) III, I, IV, II&#10;C) II, IV, I, III&#10;D) I, IV, II, III

Accepted Answer

The answer of Arrange the following in order of increasing...

Question 36

The major product of the following reaction is,&#10;

Accepted Answer

The answer of The major product of the following reaction...

Question 37

Arrange the compounds in the order of increasing acidity (least acidic first).&#10; &#10;A) II, IV, I, III&#10;B) III, IV, I, II&#10;C) IV, III, II, I&#10;D) I, III, IV, II

Accepted Answer

The answer of Arrange the compounds in the order of...

Question 38

Which is the major product of the following reaction?&#10; &#10;A) 2-mercapto-2-methyl-3-pentanol&#10;B) 3-mercapto-2-methyl-2-pentanol&#10;C) 2-methyl-2,3-pentanediol&#10;D) 4-methyl-3,4-pentanediol

Accepted Answer

The answer of Which is the major product of the...

Question 39

Which is the product of the following reaction?&#10; &#10; &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

The answer of Which is the product of the following...

Question 40

Which structures have the correct IUPAC name?

I: cis-1,2-dimethoxycyclohexane II: R-2-methoxy-1-propanol

III: 2-methoxypropane IV: trans-1,3-cyclohexanediol

A) I, II
B) III, IV
C) II, III
D) I, IV

Accepted Answer

The answer of Which structures have the correct IUPAC name?&#10;...

Question 41

The strongest acid in the following list is water.&#10;

Accepted Answer

The answer of The strongest acid in the following list...

Question 42

The major product of the following reaction is,&#10;

Accepted Answer

The answer of The major product of the following reaction...

Question 43

The following compounds are listed in decreasing boiling point order (highest first).&#10;

Accepted Answer

The answer of The following compounds are listed in decreasing...

Question 44

The following compounds are listed in decreasing order of solubility in water (highest first).&#10;

Accepted Answer

The answer of The following compounds are listed in decreasing...

Question 45

The following compound is named 1-chloro-2,2-dimethyl-4-pentanol.&#10;

Accepted Answer

The answer of The following compound is named 1-chloro-2,2-dimethyl-4-pentanol.&#10; ...

Question 46

The major product of the reaction of 3-methyl-2-butanol with hot, concentrated sulfuric acid is 3-methyl-1-butene.

Accepted Answer

The answer of The major product of the reaction of...

Question 47

The starting material needed to complete the following reaction is,&#10;

Accepted Answer

The answer of The starting material needed to complete the...

Question 48

The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,&#10;

Accepted Answer

The answer of The reaction arrows (curved arrows) required to...

Question 49

The following compounds are listed in increasing order of solubility in water (lowest first).&#10;

Accepted Answer

The answer of The following compounds are listed in increasing...

Question 50

The starting material needed to complete the following reaction is,&#10;

Accepted Answer

The answer of The starting material needed to complete the...

Question 51

The reagent needed to complete the following reaction is,&#10;

Accepted Answer

The answer of The reagent needed to complete the following...

Question 52

The major product of the reaction of 1-propanol with PCC is propanoic acid.

Accepted Answer

The answer of The major product of the reaction of...

Question 53

The product of the reaction of methanol with sodium metal is sodium methoxide.

Accepted Answer

The answer of The product of the reaction of methanol...

Question 54

The following compounds are listed in decreasing boiling point order (highest first).&#10;

Accepted Answer

The answer of The following compounds are listed in decreasing...

Question 55

The following compound is named 2,6-dimethyl-1,4-cyclohexanediol.&#10;

Accepted Answer

The answer of The following compound is named 2,6-dimethyl-1,4-cyclohexanediol.&#10; ...

Deck 8: Alcohols, Ethers, and Thiols