Chapter 17: Q42E (page 567)
What Grignard reagent and what carbonyl compound might you startwith to prepare the following alcohols?
(a)
(b)
(c)
(d)
(e)
(f)
Short Answer
(a)
(b)

(c)

(d)
(e)
(f)

(a)

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Chapter 17: Q42E (page 567)
What Grignard reagent and what carbonyl compound might you startwith to prepare the following alcohols?
(a)
(b)
(c)
(d)
(e)
(f)
(a)
(b)

(c)

(d)
(e)
(f)

(a)

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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.
Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

Question: What reagent would you use to accomplish each of the following reactions?
(a)

(b)

(c)

Question: Give IUPAC names for the following compounds:






Starting from testosterone (Problem 17-62), how would you prepare the following substances?
a.

b.

c.

d.

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