Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
9th Edition
ISBN: 9781305922198
Author: John E. McMurry
Publisher: CENGAGE L
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Chapter 27.SE, Problem 14MP
Interpretation Introduction
Interpretation:
A mechanistic pathway for the biosynthesis of caryophyllene is to be given.
Concept introduction:
The steps involved in the biosynthesis of caryophyllene are i) Elimination of the diphosphate to yield cyclic carbocation ii) Formation of a bicycle carbocation iii) Deprotonation by base.
To give:
A mechanistic pathway for the biosynthesis of caryophyllene.
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Write the complete common (not IUPAC) name of each molecule below.
Note: if a molecule is one of a pair of enantiomers, be sure you start its name with D- or L- so we know which enantiomer it is.
molecule
Ο
C=O
common name
(not the IUPAC
name)
H
☐
H3N
CH₂OH
0-
C=O
H
NH3
CH₂SH
H3N
☐
☐
X
G
(Part A) Provide structures of the FGI products and missing reagents (dashed box)
1 eq Na* H*
H
-H
B1
B4
R1
H2 (gas)
Lindlar's
catalyst
A1
Br2
MeOH
H2 (gas)
Lindlar's
catalyst
MeO.
OMe
C6H1402
B2
B3
A1
Product carbons' origins
Draw a box around product
C's that came from A1.
Draw a dashed box around
product C's that came from B1.
Classify each of the amino acids below.
Note for advanced students: none of these amino acids are found in normal proteins.
X
CH2
H3N-CH-COOH3N-CH-COO-
H3N-CH-COO
CH2
CH3-C-CH3
CH2
NH3
N
NH
(Choose one) ▼
(Choose one)
S
CH2
OH
(Choose one) ▼
+
H3N-CH-COO¯
CH2
H3N CH COO H3N-CH-COO
CH2
오오
CH
CH3
CH2
+
O
C
CH3
O=
O_
(Choose one)
(Choose one) ▼
(Choose one)
G
Chapter 27 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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