EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction
involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of
this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with
diazomethane yields cycloheptanone.
CH2N2, ether
+ N2
Draw the structure of the organic product(s) of the ring expansion of this compound:
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co
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In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.
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- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- When 1,4-dibromobutane was treated with excess ethanamine at propanone, the main product had the molecular formula C6H13N. Deduce the structure of this product by proposing a mechanism for the reaction.arrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain in complete words what this observation tells you about the mechanism of the reaction.arrow_forwardPlease provide a step by step list explaining the mechanism for the reactionsarrow_forward
- Rank the following carboxylic acids derivatives based on their reactivity towards nucleophiles (1-most reactive - 4- least reactive), and describe the structural features you use to detrmine your ranking.arrow_forwardPropose mechanisms and draw reaction-energy diagrams for the following reactions. Pay particular attention to the structures of any transition states and intermediates. Compare the reaction-energy diagrams for the two reactions, and explainthe differences.(a) 2-Bromo-2-methylbutane reacts with sodium methoxide in methanol to give 2-methylbut-2-ene (among other products).(b) 2-Bromo-2-methylbutane reacts in boiling methanol to give 2-methylbut-2-ene (among other products)arrow_forwardAn elimination step is involved in the synthesis of aromatic amino acids. We can also envision this occurring in a laboratory setting with a strong base. Provide a 1 step mechanism for this decarboxylation reaction. Note: under strongly basic conditions, hydroxide is a reasonable leavinggroup.arrow_forward
- When 2,2-dibromo-1-phenylpropane is heated overnight with sodium amide at 150 °C, the major product (after addition of water) is a different foul-smelling compound of formula C9H8. Propose a structure for this product, and give a mechanism to account for its formation.arrow_forwardProvide reagents/conditions to accomplish the following syntheses. Several steps are required in some cases.arrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific. Using the text submission box below, explain what this observation tells you about the mechanism of the reaction.arrow_forward
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