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(a) Draw all five isomers of formula(including stereoisomers).

(b) For each structure, show how many types of would appear in the proton NMR spectrum.

(c) For each structure, show how many types ofwould appear in theNMR spectrum.

(d) If an unknown compound of formulashows three types of and three types of ,can you determine its structure from this information?

Short Answer

Expert verified

(a)There are five isomers of formula , including stereoisomers, these are the following:

(d)If an unknown compound of formula shows three types of and three types of, then the proposed structure will be 1,1-dibromopropane.


Step by step solution

01

Explanation of part (a):

Isomers are molecules that have the same molecular formula but have a different arrangement of the atoms in space. These molecules differ in properties and the arrangement of atoms. Structural and stereoisomerism are two types of isomerism which can be further classified into different subtypes. Including stereoisomers, there are total five isomers of formula , these are:

02

Explanation of part (b):

Proton-NMR is the technique which can help us confirm the structure of organic compounds. Multiplicity in NMR provides the information about the proton neighbors for a particular atom or group of atoms. Number of protons which appear in proton-NMR spectrum of the isomers of molecular formula have been marked a,b,c,d in the following structures:

In structure-3 and 4, there are four types of hydrogen that would give signal in proton-NMR spectrum. Due to presence of chiral center, the adjacent protons of methylene group become diastereotopic which would give different signal in proton-NMR spectrum.

03

Explanation of part (c):

In carbon-NMR spectrum, each peak identifies a carbon atom in a different environment within the molecule. If two or more carbon atoms in a compound have exactly the same environment, then they will be represented by a single line. Number of carbons which appear in carbon-NMR spectrum of the isomers of molecular formula have been marked a,b,c in the following structures:

04

Explanation of part (d):

Three types of hydrogen and three types of carbons can be only one isomer, that is, 1,1-dibromopropane. It has three types of hydrogens that would give different signals of different chemical shifts in proton-NMR spectrum and three types of carbon atoms that would give different signals in carbon-NMR spectrum.

Structure of compound having three types of hydrogen and three types of carbon atoms

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Most popular questions from this chapter

Determine the ratios of the peak areas in the following spectra. Then use this information, together with the chemical shifts, to pair up the compounds with their spectra. Assign the peaks in each spectrum to the protons they represent in the molecular structure.

Possible structures:

  1. Show which carbon atoms correspond with which peaks in the 13CNMR spectrum of butan-2-one (Figure 13-45).
  2. Draw the proton NMR spectrum you would expect for butan-2-one. How well do the proton chemical shifts predict the carbon chemical shifts using the 鈥15 to 20 times as large鈥 rule of thumbs?

Propose mechanisms to show the interchange of protons between ethanol molecules under

  1. Acid catalysis
  2. Base catalysis.

Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown. The proton NMR of 2-methylpropanal shows the two methyl groups as equivalent (one doublet at 未 1.1), yet the product alcohol, a racemic mixture, shows two different 3H doublets, one at 未 0.75 and one around 未 1.0

(a)Draw a Newmann projection of the product along the C1-C2 axis.
(b)Explain why the two methyl groups have different NMR chemical shifts. What is the term applied to protons such as these?

Each of these four structures has molecular formula . Match the structure with its characteristic proton NMR signals. (Not all of the signals are listed in each case.)

(a) Sharpsinglet at未8.0 andtriplet at未4.0

(b) Sharpsinglet at未2.0 andquartet at未4.1

(c) Sharpsinglet at未3.7 andquartet at未2.3

(d) Broadsinglet at未11.5 andtriplet at未2.3

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