ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Textbook Question
Chapter 18, Problem 44P
Suggest a reasonable mechanism for each of the following reactions:
(a)
(b)
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(a)
(b)
(c)
Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw
the starting material(s), key reagent and a full reaction mechanism including an
explanation of the observed geometry.
Which of the following (B) and (C) will favour the enol form? Briefly explain your
reasoning.
Predict the product(s) and provide a mechanism for each of the following
transformations:
(i)
(ii)
OMe
OMe
Base
OEt
NaOEt
Propose suitable reagents to accomplish the following transformations.
Explain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.
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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- Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forward5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forward(c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forward
- Propose a synthesis for each of the following compounds. (a) OH (b) (c)arrow_forwardPropose a reasonable synthesis for each of the following compounds from the indicated starting materials and any other reagents.arrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forward
- Each of the following can be prepared by an intramolecular aldol condensation of a diketone. Apply retrosynthetic analysis to deduce the structure of the diketone in each case.arrow_forwardWhen compound (7) is subjected to reaction (5) a different compound (9) with a formula of C9H18O2 is obtained. Draw the chemical structure of the product (9) and provide a detailed mechanism for its formationarrow_forward(c) Consider the antiallergy medication loratadine (Claritin) shown below: Loratadine (Claritin) The reaction to form the portion of the molecule in the red circle is used in the synthesis of loratadine and many other pharmaceutical agents. (i) Propose a suitable starting material and reagents to form the portion of the molecule in the red circle. (ii) Clearly outline the mechanism by which the reaction takes place. In your answer, show how the intermediate ion is stabilized.arrow_forward
- Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardCan you help me answer 5.35arrow_forwardPredict the major organic product of each of the following reactions or provide the reagent needed to complete each transformation.arrow_forward
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