Reactions Types

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Organic Chemistry › Reactions Types

Questions 1 - 10
1

Which of the following sets of bases are listed from most basic to least basic?

Explanation

The correct ranking from most basic to least basic is:

The best bases are negatively charged, and the worst bases are positively charged (acidic). The stronger the base, the weaker (more stable) it's conjugate acid. An alkane is a very stable conjugate acid, which tells us that is the most basic of the set.

We know based on charge alone, that is more basic than but less basic than or .

We know that is more basic because the electronegativity of is less than that of . This means the lone pair of electrons on are held less tightly and more likely to pick up a proton.

2

What is the major product of the following reaction?

Image1

None of these

Explanation

The reaction shown is a Markovnikov addition of a hydracid (HX) across a double bond. According to Markovnikov's rule, the hydrogen gets added to the lesser-substituted carbon in the double bond, and the halide (in this case, ) gets added to the more-substituted carbon. Thus, the correct answer is .

3

Which of the following sets of bases are listed from most basic to least basic?

Explanation

The correct ranking from most basic to least basic is:

The best bases are negatively charged, and the worst bases are positively charged (acidic). The stronger the base, the weaker (more stable) it's conjugate acid. An alkane is a very stable conjugate acid, which tells us that is the most basic of the set.

We know based on charge alone, that is more basic than but less basic than or .

We know that is more basic because the electronegativity of is less than that of . This means the lone pair of electrons on are held less tightly and more likely to pick up a proton.

4

Which of the following reaction conditions favors an E1 reaction mechanism?

Weak base

Strong base

Weak nucleophile

Strong nucleophile

Aprotic solvent

Explanation

E1 reactions occur in two steps. First, the leaving group is removed, yielding a carbocation. Second, a weak base removes a proton from the carbon adjacent to the carbocation carbon. Thus, to favor E1, a protic solvent is desired in order to stabilize the carbocation. Weak bases favor an E1 mechanism.

5

Screen shot 2016 02 21 at 6.39.46 am

Classify the type of reaction given.

Elimination

Rearrangement

Substitution

Addition

Explanation

An elimination reaction occurs when there is a release of atoms in a given compound to produce two or more products. In the reaction given a hydrogen and chloride atom are eliminated from the original compound to form hydrochloric acid and ethylene.

6

Which of the following reaction conditions favors an E1 reaction mechanism?

Weak base

Strong base

Weak nucleophile

Strong nucleophile

Aprotic solvent

Explanation

E1 reactions occur in two steps. First, the leaving group is removed, yielding a carbocation. Second, a weak base removes a proton from the carbon adjacent to the carbocation carbon. Thus, to favor E1, a protic solvent is desired in order to stabilize the carbocation. Weak bases favor an E1 mechanism.

7

Screen shot 2015 11 09 at 2.33.03 pm

Screen shot 2015 11 09 at 2.41.49 pm

II only

I only

I and II

III only

Explanation

Cyanide is a weak base and a good nucleophile, and the solvent is aprotic; therefore, the product is favored. This involves 100% inversion of stereochemistry; therefore II is favored.

8

A compound can be hydrogenated by platinum metal and hydrogen to give . How many rings and double bonds does the original compound have?

The original compound has no triple bonds.

3 double bonds and 2 rings

3 double bonds and 1 ring

4 double bonds and 1 ring

4 double bonds and 2 rings

None of the other answers

Explanation

Hydrogenation of a double bond involves the bond breaking and a hydrogen being added to each carbon of that double bond. You can tell the number of double bonds by taking the number of hydrogens added and dividing it by 2.

6 added hydrogen divided by 2 is 3 double bonds.

A hydrocarbon with zero degrees of unsaturation and carbons has hydrogens. For every two hydrogens less than , there is one degree of unsaturation. After hydrogenation, our final product has no double bonds. After calculation, we see that it has two degrees of unsaturation. This means that it has two rings.

9

Screen shot 2015 11 09 at 2.33.03 pm

Screen shot 2015 11 09 at 2.41.49 pm

II only

I only

I and II

III only

Explanation

Cyanide is a weak base and a good nucleophile, and the solvent is aprotic; therefore, the product is favored. This involves 100% inversion of stereochemistry; therefore II is favored.

10

Screen shot 2016 02 21 at 6.39.46 am

Classify the type of reaction given.

Elimination

Rearrangement

Substitution

Addition

Explanation

An elimination reaction occurs when there is a release of atoms in a given compound to produce two or more products. In the reaction given a hydrogen and chloride atom are eliminated from the original compound to form hydrochloric acid and ethylene.

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