ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
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Chapter 12, Problem 49PP
Interpretation Introduction
Interpretation: The reduction or oxidation processes that are occurring in the reaction are to be determined.
Concept introduction: The term oxidation means loss of electrons and reduction means a gain of electrons. The entity which gets oxidized attains a positive charge on the atom and reduced gets a negative charge on the atom.
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2.) Draw 1 isomer of the compounds in item no. 3, and state the type of isomerism.
Example: 2-hydroxy-pentanal
OH
Structure:
Isomer:
OH
Type of isomerism: Functional Isomerism
3.) Predict the product of the following chemical reactions and state where the product (waste) should the
waste should be disposed:
Example:
OH
1. NaBH, ethanol
2. HO
CH,CH,CH,CH
CH;CH,CH,CH
H
Butanal
1-Butanol
Waste: G704 (Non-halogenated organic solvents)
1. NaBH,, ethanol
a.) Cyclohexanecarbaldehyde 2. H,O"
b.) Sodium Flouride + 3-iodo-3-methylpentane
(hint: substitution or elimination?)
c.) Benzoic acid + Phenol
РСС
d.) 3-pentanol
H>CrO4
e.) Cyclohexylmethanol
5. Ribose's structure is
ОН
HO
ОН ОН
a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring.
b) What is the name of the resulting functional group?
c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create
this functional group is typically not thermodynamically favored, why does most ribose in
water exist as a 5-membered ring? A few word answer is fine.
d) AG°for this reaction is about - 5 kJ/mol. Assuming that you start with a 1 mM solution of
ribose in water, what is the approximate concentration at equilibrium of (i) the linear form?
(ii) The cyclic form? (A good answer should be correct within 20%, e.g. it is fine to
approximate 9 mM as 10 mM, but it is not okay to approximate 0.1 mM as 1 mM.)
e) This reaction creates a new stereocenter. Please indicate it with a *.
f) Consider the starting point for synthesis of purines like ATP, which is PRPP
(pheseboribosylevOrhesehate)
НО НО
LOLOH
HO
ОН
HO
OH
Pyrophosphate…
4. Complete each of the following reactions by drawing the structures of the organic products.
a)
b)
c)
H₁₂O'
beat
B
H.SO
heat
6
Chapter 12 Solutions
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
Ch. 12.1 - Prob. 1LTSCh. 12.1 - Prob. 1PTSCh. 12.1 - Prob. 2ATSCh. 12.1 - Prob. 3CCCh. 12.2 - Prob. 4CCCh. 12.3 - Prob. 8CCCh. 12.3 - Prob. 9CCCh. 12.4 - Prob. 3LTSCh. 12.4 - Prob. 10PTSCh. 12.4 - Prob. 11ATS
Ch. 12.4 - Prob. 4LTSCh. 12.4 - Prob. 12PTSCh. 12.4 - Prob. 13ATSCh. 12.6 - Prob. 14CCCh. 12.6 - Prob. 5LTSCh. 12.6 - Prob. 15PTSCh. 12.6 - Prob. 16PTSCh. 12.7 - Prob. 18CCCh. 12.9 - Prob. 6LTSCh. 12.9 - Prob. 19PTSCh. 12.9 - Prob. 20ATSCh. 12.9 - Prob. 21CCCh. 12.10 - Prob. 7LTSCh. 12.10 - Prob. 22PTSCh. 12.10 - Prob. 23ATSCh. 12.13 - Prob. 8LTSCh. 12.13 - Prob. 24PTSCh. 12.13 - Prob. 25ATSCh. 12.13 - Prob. 26CCCh. 12.13 - Prob. 9LTSCh. 12.13 - Prob. 27PTSCh. 12.13 - Prob. 28ATSCh. 12 - Prob. 29PPCh. 12 - Prob. 30PPCh. 12 - Prob. 31PPCh. 12 - Prob. 32PPCh. 12 - Prob. 33PPCh. 12 - Prob. 34PPCh. 12 - Prob. 35PPCh. 12 - Prob. 36PPCh. 12 - Prob. 37PPCh. 12 - Prob. 38PPCh. 12 - Prob. 39PPCh. 12 - Prob. 40PPCh. 12 - Prob. 41PPCh. 12 - Prob. 42PPCh. 12 - Prob. 43PPCh. 12 - Prob. 44PPCh. 12 - Prob. 45PPCh. 12 - Prob. 46PPCh. 12 - Prob. 47PPCh. 12 - Prob. 48PPCh. 12 - Prob. 49PPCh. 12 - Prob. 50PPCh. 12 - Prob. 51PPCh. 12 - Prob. 52PPCh. 12 - Prob. 53ASPCh. 12 - Prob. 54ASPCh. 12 - Prob. 55ASPCh. 12 - Prob. 62IPCh. 12 - Prob. 64IPCh. 12 - Prob. 65IPCh. 12 - Prob. 66IPCh. 12 - Prob. 67IPCh. 12 - Prob. 68IPCh. 12 - Prob. 69IPCh. 12 - Prob. 74IP
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