Chapter 13: Q 46. (page 523)
Question: Tell how IR spectroscopy could be used to determine when each reaction is complete.
Short Answer
Answer
The change in functional groups of the starting material of the product helps in predicting the product.
Chapter 13: Q 46. (page 523)
Question: Tell how IR spectroscopy could be used to determine when each reaction is complete.
Answer
The change in functional groups of the starting material of the product helps in predicting the product.
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Get started for freeQuestion:(a) What mass spectral fragments are formed by α cleavage of butan-2-ol, ?
(b) What fragments are formed by dehydration of butan-2-ol?
Question: Reaction of tert-butyl pentyl ether with HBr forms 1-bromopentane and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150–3000, 3000–2850, and 1650 cm-1. Propose a structure for B and draw a stepwise mechanism that accounts for its formation.
Question:Primary (1°) alcohols often show a peak in their mass spectra at m/z= 31. Suggest a structure for this fragment.
Question: Reaction of BrCH2CH2CH2CH2NH2 with NaH forms compound W, which gives the IR and mass spectra shown below. Propose a structure for W and draw a stepwise mechanism that accounts for its formation.
Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.
a. Identify the structures of A and B.
b. Draw a mechanism for the conversion of citronellol to isopulegone.
c. Draw a mechanism for the conversion of isopulegone to B.
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