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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Galactose, a constituent of the disaccharide lactose found in dairy products, is metabolized by a pathway that includes the isomerization of UDP-galactose to UDP-glucose, where UDP = uridylyl diphosphate. The enzyme responsible for the transformation uses as cofactor. Propose a mechanism.

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.
Question:Which of the eight alcohols that you identified in Problem 17-38 react with in aqueous acid? Show the products you would expect from each reaction
Question: Give IUPAC names for the following compounds:






The NMR spectrum shown is that of 3-methyl-3-buten-1-ol. Assign
all the observed resonance peaks to specific protons, and account for
the splitting patterns.

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