Draw eugenol as a line structure. The double bonds of the benzene ring are fairly unreactive unless you use special catalysts. But the double bond on the side group is reactive. Draw the mechanism of eugenol reacting with HBr to form the two possible carbocation intermediates. Put your intermediates into square brackets. Label each carbocation as a methyl carbon or 1°, 2°, or 3°. Then circle a more stable carbocation if one is more stable. Can you guess what the final product is?

Draw eugenol as a line structure. The double bonds of the benzene ring are fairly unreactive unless you use special catalysts. But the double bond on the side group is reactive. Draw the mechanism of eugenol reacting with HBr to form the two possible carbocation intermediates. Put your intermediates into square brackets. Label each carbocation as a methyl carbon or 1°, 2°, or 3°. Then circle a more stable carbocation if one is more stable. Can you guess what the final product is?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 7E: When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2)...

See similar textbooks

Similar questions

Draw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up. a. ZnCl2 + CH3OH b. FeBr3 + Br c. AlCl3 + Cl−
draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocation
The pictured reaction shows an alkyl bromide being converted into an alkene. Choose all reagents that would produce the pictured alkene as the major product. A) NaOH/H2O B) H2O C) tBuOK/tBuOH D) EtONa/EtOH
TRUE OR FALSE I. The reaction of BH3 with 2-methylbut-2-ene results in the attachment of a hydroxyl group, OH, on the third carbon since this carbon is less substituted. II. The reduction of an alkyne using a strong base such as LiNH2 gives an alkane when 2 equivalents of hydrogen gas is added. III. Hydrobromination of an alkene follows anti-Markovnikov’s rule in the presence of a peroxide.
Ignoring E and Z isomers, what two enols are formed when pent-2-yne is treated with H2O, H2SO4, and HgSO4? Draw the ketones formed from these enols after tautomerization.
Choose the one has the highest priority, and the one has the lowest. (Please show why) -CHO -COOH -COCH3 -CONH2
When carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be? Forms more of one enantiomer than another because of steric reasons around the carbonyl Forms more of one enantiomer than another depending on the temperature of the reaction Forms different products depending on the solvent used Forms a racemic mixture of the two possible enantiomers
1. You have an alkyl halide and the product has a thiol group without an alkyl, what is the reagant? 2. What is the reaction of disodium sulfide and Na2S, what is its product? 3. You have a thiol compound that reacts with sodium hydroxide, what do you get? 4. You have an oxyrane reacting with sulfuirc acid and methanol, what do you get? 5. Have an alkene reacting with Br, what do you get?
When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?
When (CH3CH2)3CBr is added to CH3OH at room temperature, the major product is (CH3O)C(CH2CH3)3 and a minor product is CH3CH=C(CH2CH3)2. Propose a mechanism for the product that is formed by the substitution reaction. Use curved arrows to show the movement of electrons.
What are the reagents used to convert 2-butyne to C4H8? What are the products when that C4H8 is mixed with OsO4, and H2O (the formula will be C4H10O2 racemic)? What is the product when C4H8 is mixed with RCO3H, and H2O (the formula will be C4H10O2 meso)?
True or False 1. With alkynes having 2 pi bonds, they have more electron-rich region than alkenes and, thus, are more reactive than alkenes. 2. Hydrobromination of an alkene follows anti-Markovnikov’s rule in the presence of a peroxide. 3. The reaction of BH3 with 2-methylbut-2-ene results in the attachment of a hydroxyl group, OH, on the third carbon since this carbon is less substituted. 4. The reduction of an alkyne using a strong base such as LiNH2 gives an alkane when 2 equivalents of hydrogen gas is added.