Chapter 17: Q38E (page 567)
Draw and name the eight isomeric alcohols with the formula C5H12O
Short Answer
Isomers followed as:

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Chapter 17: Q38E (page 567)
Draw and name the eight isomeric alcohols with the formula C5H12O
Isomers followed as:

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Draw structures corresponding to the following IUPAC names:
Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

Question: Predict the products of the following reactions:
(a)

(b)

(c)

A compound of unknown structure gave the following spectroscopic data:
Mass spectrum:
IR:
NMR: 1.4 (2H, quartet, J=7Hz); 1.2 (6H, singlet); 1.0 (1H, singlet); 0.9 (3H, triplet, J=7Hz)
NMR: 74, 35, 27, 25
(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.
(b) How many protons (H) does the compound contain?
(c) What functional group(s) does the compound contain?
(d) How many carbons does the compound contain?
(e) What is the molecular formula of the compound?
(f) What is the structure of the compound?
(g) Assign peaks in the molecule’s NMR spectrum corresponding to specific protons.
What alcohols would give the following products on oxidation?
(a)

(b)

(c)

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