Organic Chemistry

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Questions 1 - 10
1

What is the IUPAC name of the following compound?

Untitled

3-bromo-2-methylcyclohexene

None of the other answers

1-bromo-2-methyl-2-cycloxene

6-bromo-1-methylcyclohexene

2-bromo-1-methylcyclohexene

Explanation

The numbering of the molecule begins across the double bond and goes in the direction where the lowest numbers for substituents can be achieved. Thus, the methyl group will be on carbon two and the bromine on carbon 3. Substituents are ordered alphabetically. The base molecule is a six-membered ring with one double bond. This is called a cyclohexene.

2

Which of the following substrates would have the fastest reaction rate for an SN1 mechanism?

Explanation

The SN1 mechanism involves the formation of a carbocation intermediate in the rate-determining step. The most stable carbocation will produce the fastest reaction. We can immediately eliminate any answer choices that will produce primary or secondary carbocations, since a tertiary carbocation will be much more stable. When comparing tertiary carbocations, larger and more electronegative substituents will allow for more charge stabilization.

Since the tertiary carbocation formed by the dissociation of iodide from will the be most stable, this substrate will react the fastest.

3

What is the IUPAC name of the following compound?

Untitled

3-bromo-2-methylcyclohexene

None of the other answers

1-bromo-2-methyl-2-cycloxene

6-bromo-1-methylcyclohexene

2-bromo-1-methylcyclohexene

Explanation

The numbering of the molecule begins across the double bond and goes in the direction where the lowest numbers for substituents can be achieved. Thus, the methyl group will be on carbon two and the bromine on carbon 3. Substituents are ordered alphabetically. The base molecule is a six-membered ring with one double bond. This is called a cyclohexene.

4

Which element is present in all organic compounds?

Carbon

Nitrogen

Oxygen

Phosphorous

Explanation

By definition, an organic compound is a compound that contains carbon. Organic chemistry is the study of carbon-containing molecules.

5

Screen shot 2016 01 17 at 12.54.25 pm

What is the product of the reaction given?

Screen shot 2016 01 17 at 12.59.54 pm

Screen shot 2016 01 17 at 1.00.01 pm

Screen shot 2016 01 17 at 1.00.12 pm

Screen shot 2016 01 17 at 1.00.06 pm

Explanation

In the reaction below, a ketone is protonated by a strong acid. This triggers the deprotonation of the weakly acidic hydrogen bonded to the alpha carbon by a bromide ion and formation of an alkene functional group.

Screen shot 2016 01 17 at 1.00.53 pm

6

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.

7

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.

8

What is the IUPAC name for the following compound?

Screen shot 2016 02 17 at 7.32.41 pm

Explanation

The longest carbon chain is carbons long (thus ""), and the lack of double bonds makes it an alkane (thus ""). The highest priority functional group is the carboxylic acid group, and the suffix of the IUPAC name should reflect the highest priority functional group (thus ""). Because the carboxylic acid group is assumed to lie on carbon number there is no need to designate a locand for this functional group. The other substituents of this molecule are the methyl groups on carbons and when numbering the chain from left to right. Thus, the name is .

9

Octagon

Assuming that this molecule is planar, determine whether this molecule is aromatic, and name the number of electrons ( molecular orbitals).

Not aromatic, 8 electrons

Aromatic, 8 electrons

Aromatic, 6 electrons

Non aromatic, 6 electrons

Explanation

There is no p orbital surrounding the Boron atom, so the ring does not have a fully conjugated pi system. In addition, there are 8 electrons, which does not follow Huckel's rule (an aromatic system contains 4n+2 electrons). The pi electrons include the lone pair (not shown, but implicit) on the nitrogen atom, which is why the answers with "6 electrons" are not correct.

10

Ephedrine (shown below) contains what type of amine?

Mcat_problem_set_1

Secondary

Primary

Tertiary

Quaternary

Neutral

Explanation

A secondary amine is an amine (nitrogen atom) that is attached to two carbon-containing groups (alkyl groups or aryl groups). The nitrogen in ephedrine is attached to two alkyl groups, making it a secondary amine.

Primary amines are generally written as . Secondary amines are generally written as . A tertiary amine will be bound to three different R-groups. Quaternary amines require a positive charge on the nitrogen atom to accommodate a fourth R-group.

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