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Chapter 13: Q.12P (page 671)

Draw a splitting tree, similar to Figures 13-32 and 13-33, for proton Hc in styrene. What is the chemical shift of proton Hc?

Short Answer

Expert verified

Answer

The splitting tree is:

The signal Hc is split ( Jac =11HZ) by coupling with Haand further split( Jbc =2HZ) by coupling with Hb .

Step by step solution

01

Styrene

The phenomenon of splitting of a single peak into various peaks is known as slitting of signals. Non-equivalent protons on adjacent carbon atoms give rise to splitting of signals. The chemical formula of styrene is C8H8 and its structure is shown below.

Structure of styrene

02

Explanation

The chemical shift (δ) of proton Hc in styrene is 3.2ppm and the splitting tree for proton is shown below.

Splitting tree

The signal Hc is split ( Jac =11HZ) by coupling with Haand further split( Jbc =2HZ) by coupling with Hb .

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Most popular questions from this chapter

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 at1.1), yet the product alcohol, a racemic mixture, shows two differentdoublets, one at0.75 and one around1.0.

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

Determine the number of different kinds of protons in each compounds

  1. 1-bromopropane (b) 2-bromopropane
  2. 2,2-dimethylpropane (d) 2,2-dimethylpentane
  3. (e) 1-chloro-4-methylbenzene (f) 1-chloro-2-methylbenzene

A laboratory student was converting cyclohexanol to cyclohexyl bromide by using one equivalent of sodium bromide in a large excess of concentrated sulfuric acid. The major product she recovered was not cyclohexyl bromide, but a compound of formula C6H10that gave the following 13CNMR spectrum:

  1. Propose a structure for this product.
  2. Assign the peaks in the 13CNMR spectrum to the carbon atoms in the structure.
  3. Suggest modifications in the reaction to obtain a better yield of cyclohexyl bromide.

Question:Using a 60-MHz spectrometer, a chemist observes the following absorption: doublet, J = 7 Hz, at 4.00

(a) What would the chemical shift () be in the 500-MHz spectrum?

(b) What would the splitting value J be in the 500-MHz spectrum?

(c) How many hertz from the TMS peak is this absorption in the 60-MHz spectrum? In the 500-MHz spectrum?

A compound(C10H1202)whose spectrum is shown here was isolated from a reaction mixture containing 2-phenylethanol and acetic acid.

  1. Propose a structure for this compound.
  2. Assign peaks to show which protons give rise to which signals in the spectrum.
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