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SOME REVIEW QUESTIONS

CHAPTERS 13 14 7 TOPICS Mass Spectrometry, Infrared Spectroscopy H1 Nuclear Magnetic Resonance Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa

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Radicals; Reactions of Alkanes


Aromaticity; Reactions of Benzene

CHAPTER 13
O C C H3 H2 H2 C H2 C O

C C H3 H2

C H3

O C C H3 H2

H2 C

C C H3 H2

H2 C O

C H3

O C C H3 H2

H2 C

C C H3 H2

H2 C O

C H3

CHAPTER 13 You start by taking a sample from each of the unlabeled containers and then recording an IR spectrum for each. The four IR spectra are recorded below. As the company IR specialist, you then are able to clearly and correctly determine the identity of the compound in each of the four unlabeled containers. The packing slip that accompanied the containers shows that the four organic compounds that were in the shipment are:
H2 C COOH

H2 C OH

II
O C H2

COOH

III

IV

CHAPTER 7 Draw the three resonance forms of the conjugate base whose structure is shown below.

. .

CHAPTER 7 Record the structures of the products from the following reaction. Use the mechanism to account for their formation.

r HC C +B C C 2 H 2 2 H H

CHAPTER 7 Complete the following equation by drawing the structures of all products.

+C H l

CHAPTER 12

Q22 Give the product(s) of each of the following reactions (disregarding stereoisomers)
heat

(a)

H2C C C C CH3 + H H2 H2

NBS
peroxide

CHAPTER 12

Q22 Give the structures of all of the mono-substituted product(s) of the following reaction (disregarding stereoisomers)

(b)

C H 3
u do v it n r a a i

l + C 2

CHAPTER 14 The mass spectrum of Compound A shows a molecular ion at 113 amu and the IR spectrum has characteristic absorptions at 2270 and 1735 cm-1. The H1 NMR spectrum is recorded below. Determine the structure of Compound A.

CHAPTER 14 (a) Based on the mass spectral data and the IR data, what functional groups are present in Compound A?

CHAPTER 14 (b) How many types of non-equivalent protons are there in Compound A?

CHAPTER 14 (c) What is the structure of Compound A?

CHAPTER 15 What is aromaticity? There is a p orbital on each carbon that is perpendicular to the plane of the ring carbon which results in an overlapping of conjugated p atomic orbitals around the ring.

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ENERGY

6* 4* 5*

The six electrons of benzene fill the three bonding molecular orbitals (MO). The two electrons in 1 are lower in energy and this extra stabilization is the resonance energy of benzene. In benzene and in other compounds that are said to be aromatic, the highest occupied molecular orbitals (HOMO) are completely filled with electrons.

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The Hckel theory concludes that a molecule is aromatic only if the molecule
has a monocyclic system of conjugation (the ring must have a cloud of electrons above and below the plane of the molecule). is planar (every atom in the ring must have a p-orbital and each p-orbital must overlap with the p-orbitals on either side of it).

has (4n+2) electrons (ie only molecules that have 2, 6, 10, 14, 18... electrons can be aromatic)

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CHAPTER 15 (a) What is the hybridization of the nitrogen in sulfathiozole?


.. S:

:N

sulfathiozole

(b) Assuming that the sulfur is sp2-hybridized, how many -electrons are there in the sulfathiozole ring?

(c) Would you expect sulfathiozole to exhibit aromatic character or not?

CHAPTER 15

What product would you expect from the following Diels-Alder reaction?

CHAPTER 15 Electrophilic addition to an aromatic occurs in three (3) steps. Show the steps in the mechanism for the electrophilic aromatic substitution reaction given below:
Br + Br2 FeBr3

STEP 1

Br + Br2 FeBr3

STEP 2

STEP 2

CHAPTER 15

What product would you expect from the following Diels-Alder reaction?

O H3C + H3C H C C H
2

C H