(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (I) 3-decyne; (II) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H2O Compound X 100 - MS-IW-5644 80- 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, deduce which of following structures corresponds to X: Br Br Br HO Br IV I H II III Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity

(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (I) 3-decyne; (II) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H2O Compound X 100 - MS-IW-5644 80- 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, deduce which of following structures corresponds to X: Br Br Br HO Br IV I H II III Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single
hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from
this alkyne.
(I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration
product.
(b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown.
Br2, H20
Compound X
100 -
MS-IW-5644
80
60
40 -
20 -
20
40
60
80
100
120
140
160
180
200
220
m/z
Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X:
Br
Br
HO,
IV
V
I
II
II
Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the
mass spectrum.
12
Relative Intensity

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