Interpretation:
Given that terminal
Concept introduction:
Addition of bromine to alkynes occurs through the formation of a cyclic bromonium ion intermediate. Water being nucleophilic, if present will attack the bromonium ion to yield an enol. The enol will then tautomerize to a
To propose:
A mechanism for the reaction in which ethynylbenzene reacts with bromine and water to yield a bromoketone is to be proposed. Further to state to what reaction of alkenes this reaction resembles.
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Chapter 9 Solutions
Organic Chemistry
- Can the following alkanes (A and B) be synthesized from the same alkene via a hydrogenation reaction? If this is possible, explain your rationale for why and draw the required alkene. If this is not possible, explain your rationale for why and draw the alkenes required to make each product. Clearly label which alkene would provide which alkane product. CI H3C Is it possible? YES or NO CH3 H3C- H- Rationale: H;C- CH2CH3 CI CH2CH3 A В Alkene(s) Structures:arrow_forwardМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3arrow_forwardThe nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.arrow_forward
- [References] Draw the alkene structure that produced the following compounds in a ozonolysis reaction as specified. 1. O3 C7H12 2. (CH3)2Sarrow_forwardGIve Introduction to Alkyne Reactions ?arrow_forwardState what alkene or alkyne (with only carbons and hydrogens) and what other reactants you should use to most effectively synthesize the following in the fewest number of steps and with the highest yield. H;C-CH,- C CH3arrow_forward
- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardThe addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically favored. What would be the product for the reaction above? Hint: Think of the self-ionization of water and the polarity of the carbonyl group.arrow_forward1) Predict the product(s) of the following alkene addition reactions. Be sure to show stereochemistry where applicable and draw out all stereoisomers formed in the reaction. HNO3 H2SO4 Br2 FeBr3 sO3 CI, AICI3 H2SO,arrow_forward
- When 4-penten-2-one is reacted with aqueous NaBH4 (sodium borohydride), the major substrate product will contain the following functional groups: alcohol only. alkene only. ketone only. alkene & alcohol. alkene & ketone, since no reaction occurs under these conditions.arrow_forwardWhich represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondarrow_forwardAlkyl halides undergo elimination reactions to produce alkenes by the reacting with strong bases as shown in the following reaction (see image). In general, compounds where the halogen is axial (axial position) are much more reactive than those in which they are in the equatorial position. Taking the above into account: a. Which of the following compounds would give a faster elimination reaction: cis-1-bromo-2-tert-butylcyclohexane or trans-1-bromo-2-tert-butylcyclohexane? Draw the corresponding structures and clearly explain the choice.arrow_forward
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