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Questions 1 - 10
1

Which of the following compounds can be considered a Lewis base?

Explanation

A Lewis base is a compound that donates a pair of electrons. The only compound shown that possesses an electron pair that can be donated is ammonia. is the Lewis base. and are Lewis acids and are therefore wrong. Neither carbon dioxide nor methane are Lewis bases.

2

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.

3

What is the IUPAC name of the molecule shown?

Img 1324

Methylcyclohexane

Methylcycloheptane

1-Methylcyclohexane

1-Methylcycloheptane

Explanation

The molecule's longest carbon chain has 6 carbons (thus, "hex-"), and the lack of double bonds makes it an alkane (thus "hexane"). The longest chain is a ring structure (thus "cyclohexane"), and the one branching group is a carbon chain consisting of one carbon and no double bonds (a "methyl" group). Because there are no other functional groups on the molecule there is no need to put a number before the location of the methyl group (thus "methylcyclohexane").

4

Img 0640

Identify the main functional groups in the pictured molecule.

Benzene, imine, aldehyde

Benzene, amide, aldehyde

Phenol, amine, ketone

Phenol, imine, ketone

Explanation

Img 0641

1. Benzene

2. Imine

3. Aldehyde

5

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.

6

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 .

7

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.

8

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.

9

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.

10

Which of the following compounds can be considered a Lewis base?

Explanation

A Lewis base is a compound that donates a pair of electrons. The only compound shown that possesses an electron pair that can be donated is ammonia. is the Lewis base. and are Lewis acids and are therefore wrong. Neither carbon dioxide nor methane are Lewis bases.

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