(a)
To determine: The mechanism for the given reaction and type of mechanism it follows.
Interpretation: The mechanism for the given reaction and type of mechanism it follows is to be identified.
Concept introduction: In an addition reaction, atoms are added in a compound that has a double and a triple bond.
In an elimination reaction, a substituent is removed from the compound and this removal of a substituent leads to the formation of a bond.
(b)
To determine: The mechanism of the given reaction.
Interpretation: The information that
Concept introduction: Steps for correct mechanism are shown below.
- The atoms that contain double bond or those containing cations act as electrophiles.
- The atoms with lone pair act as nucleophiles.
- Identify the electrophiles site in the given compound.
- Draw the arrow starting from the correct site and ending at the correct site.
Want to see the full answer?
Check out a sample textbook solutionChapter 14 Solutions
Organic Chemistry (9th Edition)
- Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. Show all required reagents and all molecules synthesized along the way.arrow_forwardWhen warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forward
- What happens to the rate of the following SN2 reaction when the 3-iodopentane is doubled and the NaCN is tripled?arrow_forwardDraw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1 ° alkyl halide.arrow_forwardExplain why the ortho-substituted 2-nitrophenol in 30-40% yield and the para-substituted 4-nitrophenol in 15% yield have different boiling points and in doing so, explain which isomer has the higher boiling point and which one has the lower boiling point?arrow_forward
- What is the major product of the reaction of 1 mol of propyne with each of the following reagents? a. HBr (1 mol) e. aqueous H2SO4, HgSO4 h. H2/Lindlar catalyst b. HBr (2 mol) f. R2BH in THF followed by i. sodium amide c. Br2 (1 mol)/CH2Cl2 H2O2/HO-/H2O j. the product of part i followed by d. Br2 (2 mol)/CH2Cl2 g. excess H2, Pd/C 1-chloropropanearrow_forwardFill in the appropriate reagents for the following reaction:arrow_forwardWhat is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction? What is the product obtained when product A reacted with ethyl acetate in the same basic solution?arrow_forward
- (S)-CH3CH(N3)CH2CH2CH3 can be synthesized by an SN2 reaction. Draw the structures of the alkyl chloride and nucleophile that will give this compound in highest yield.arrow_forwardThe biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C—C bonds in a single reaction mixture. a. Draw a stepwise mechanism for the following reaction.b. Show how X can be converted to 16,17-dehydroprogesterone.arrow_forwardWhat is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning