Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 29, Problem 41P
Draw the products formed when cholesterol is treated with each reagent. Indicate the stereochemistry around any stereogenic centers in the product.
a.
b.
c. PCC
d. oleic acid,
e. [1]
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Draw the product formed when phenylacetic acid (C6H5CH2COOH) is treated with each reagent. With some reagents, no reaction occurs.
a. NaHCO3
b. NaOH
c. SOCl2
d. NaCl
e. NH3(1equiv)
f. NH3, ∆
g. CH3OH, H2SO4
h. CH3OH, −OH
i. [1] NaOH; [2] CH3COCl
j. CH3NH2, DCC
k. [1] SOCl2; [2] CH3CH2CH2NH2 (excess)
l. [1] SOCl2; [2] (CH3)2; [2] (CH
3. What product is formed when HO(CH₂) CHO is treated with each reagent?
c. Ag₂O, NH OH
d. Na₂Cr₂O₂, H₂SO4, H₂O
a. NaBH, CH₂OH
b. PCC
400
Draw the product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction
occurs.
a. NaBH4, CH,OH
b. [1] LIAIH4; (2] H20
c. H2, Pd-C
d. PCC
e. NazCr,07, H2SO4, H2O
f. Ag,0, NH,OH
g. [1) CH,MgBr; (2] H2O
h. [1] CęH,Li; [2] H20
i. [1] (CH3),CuLi; (2] H2O
j. [1] HC=CNa; [2] H2O
k. [1] CH;C=CLi; [2] H2O
I. The product in (a), then TBDMS-CI, imidazole
Chapter 29 Solutions
Organic Chemistry (6th Edition)
Ch. 29.2 - Problem 31.1
One component of jojoba oil is a wax...Ch. 29.3 - Problem 31.2
How would you expect the melting...Ch. 29.3 - Problem 31.3
Draw the products formed when...Ch. 29.3 - Problem 31.4
The main fatty acid component of the...Ch. 29.3 - Prob. 5PCh. 29.7 - Problem 31.10
Locate the isoprene units in each...Ch. 29.7 - Problem 31.11
Locate the isoprene units in...Ch. 29.7 - Problem 31.12
Write a stepwise mechanism for the...Ch. 29.7 - Prob. 14PCh. 29.8 - Prob. 15P
Ch. 29.8 - Prob. 16PCh. 29.8 - Prob. 17PCh. 29 - 31.17 Locate the isoprene units in each...Ch. 29 - Prob. 25PCh. 29 - Locate the isoprene units in each compound. a. e....Ch. 29 - 31.27 Classify each terpene and terpenoid in...Ch. 29 - Prob. 33PCh. 29 - Draw three-dimensional structures f or each...Ch. 29 - Prob. 37PCh. 29 - Prob. 38PCh. 29 - Prob. 39PCh. 29 - Prob. 40PCh. 29 - 31.38 Draw the products formed when cholesterol is...Ch. 29 - 31.39 Draw a stepwise mechanism for the following...Ch. 29 - 31.40 Draw a stepwise mechanism for the following...Ch. 29 - Prob. 44P
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