ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 18, Problem 32P
Each of the following reaction has been reported in the chemical literature and gives a single organic product in good yield. What is the principal product in each reaction?
(a)
(b)
(c)
(d)
(e)
(f)
(g)
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Provide the reagents and solvents (where appropriate) needed to bring about the following
transformations.
(a)
CI
(b)
The reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent.
Identify compounds A, B, C, and D and give their names.
By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur?
By what mechanism does the reaction of A with strong base to form B occur?
Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.
Compound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product
(compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which
has molecular formula C7H160. Draw the structures of compounds A, B, and C.
Chapter 18 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.3 - Prob. 3PCh. 18.4 - Prob. 4PCh. 18.4 - Prob. 5PCh. 18.6 - Prob. 6PCh. 18.7 - Prob. 7PCh. 18.7 - Prob. 8PCh. 18.7 - Prob. 9PCh. 18.8 - Prob. 10P
Ch. 18.8 - Prob. 11PCh. 18.8 - Prob. 12PCh. 18.9 - Prob. 13PCh. 18.10 - Prob. 14PCh. 18.10 - Prob. 15PCh. 18.11 - Problem 18.16 The product of the following...Ch. 18.11 - Prob. 17PCh. 18.12 - Problem 18.18 What other combination of ylide and...Ch. 18.12 - Prob. 19PCh. 18.12 - Prob. 20PCh. 18.12 - Prob. 21PCh. 18.13 - Prob. 22PCh. 18 - (a) Write structural formulas and provide IUPAC...Ch. 18 - Each of the following aldehydes and ketones is...Ch. 18 - The African dwarf crocodile secretes a volatile...Ch. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Prob. 29PCh. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - Each of the following reaction has been reported...Ch. 18 - Prob. 33PCh. 18 - On standing in 17O-labeled water, both...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - The OH groups at C-4 and C-6 of methyl ...Ch. 18 - Prob. 38PCh. 18 - Prob. 39PCh. 18 - The sex attractant of the female winter moth has...Ch. 18 - Prob. 41PCh. 18 - Prob. 42PCh. 18 - Prob. 43PCh. 18 - Suggest a reasonable mechanism for each of the...Ch. 18 - Prob. 45PCh. 18 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Prob. 49PCh. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Prob. 52DSPCh. 18 - Prob. 53DSPCh. 18 - Prob. 54DSPCh. 18 - Prob. 55DSPCh. 18 - Prob. 56DSPCh. 18 - Prob. 57DSPCh. 18 - Prob. 58DSP
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