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Questions 1 - 10
1

What is the IUPAC name for the following compound?

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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 .

2

Identify the given organic functional group.

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Aldehyde

Carboxylic acid

Acid anhydride

Ketone

Ester

Explanation

Aldehydes are carbonyls with one R-group and one hydrogen attached to the carbonyl carbon.

3

Ephedrine (shown below) contains what type of amine?

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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.

4

Identify the given organic functional group.

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Aldehyde

Carboxylic acid

Acid anhydride

Ketone

Ester

Explanation

Aldehydes are carbonyls with one R-group and one hydrogen attached to the carbonyl carbon.

5

This molecule contains a carbonyl functional group. One substituent of the carbonyl carbon is a hydrogen. What is this molecule?

Aldehyde

Ketone

Acid

Amino acid

Explanation

A carbonyl functional group takes the form of . This leaves the carbonyl carbon to form two remaining bonds with various substituents. If one of these substituents is a hydrogen, the molecule is an aldehyde (the carbonyl group is at the end of the carbon chain). If neither substituent is a hydrogen, the molecule is a ketone (the carbonyl group is not at the end of the carbon chain).

An acid contains the carboxylic acid functional group, which takes the form of . Carbonyl groups do not contain the .

Amino acids contain the carboxylic acid functional group () and an amine functional group (). The description in the question does not fit this molecule.

6

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.

7

What is the major product of the following reaction?

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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 .

8

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.

9

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.

10

Which statement is not true regarding stereoisomers?

Corresponding stereoisomers have the same biological properties

Corresponding stereoisomers have the similar physical properties except for the rotation of light

Corresponding stereoisomers have the same molecular formulas

Diastereomers are easier to separate than enantiomers

Explanation

Corresponding stereoisomers differ in biological properties. The inversion of just one stereocenter on a large, complex molecule can alter the biological properties of the entire molecule. All other statements are true.

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