Get answer: Draw the products of the following reactions. If the products can exist as

Show how each of the following compounds can be synthesized from an alkene:

Explain why 3-methylcyclohexene should not be used as the starting material in Problem 52b.

What is the major product of each of the following reactions?

Which electrophilic addition reactions a. form a carbocation intermediate? c. form a three-membered ring intermediate? b. form no intermediate? d. form a five-membered ring intermediate?

Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

Give two names for each of the following:

What reagents are needed to synthesize the following alcohols?

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

Draw curved arrows to show the flow of electrons responsible for the conversion of the following reactants into products:

What reagents are needed to carry out the following syntheses?

a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement. b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)

What is the major product of each of the following reactions?

Using any alkene and any other reagents, how would you prepare the following compounds?

Which is more stable?

a. Use curved arrows to show the flow of electrons that occurs in each step of the following mechanism. b. Draw a reaction coordinate diagram for the reaction. (Hint: An alkyl halide is more stable than an alkene.)

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed. 1. HCl 4. Br2 in CH2Cl2 7. H2O + H2SO4 2. BH3/THF, followed by HO-, H2O2, H2O 5. Br2 + H2O 8. CH3OH + H2SO4 3. a peroxyacid 6. H2 + Pd/C

1-Methylcyclohexene forms two products when it reacts with bromine in methanol. a. Draw the mechanism for the formation of the products. b. Describe their stereochemical relationshipthat is, are they enantiomers or diastereomers?

The second-order rate constant (in units of M- 1s - 1) for acid-catalyzed hydration at 25 C is given for each of the following alkenes:a. Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 * 10 - 8.) b. Why does (Z)-2-butene react faster than (E)-2-butene? c. Why does 2-methyl-2-butene react faster than (Z)-2-butene? d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?

Which compound has the greater dipole moment?

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

A student was about to turn in the products he had obtained from the reaction of HI with 3,3,3-trifluoropropene when he realized that the labels had fallen off his flasks and he did not know which label belonged to which flask. His friend reminded him of the rule that says the electrophile adds to the sp2 carbon bonded to the most hydrogens. In other words, he should label the flask containing the most product 1,1,1-trifluoro-2-iodopropane and label the flask containing the least amount of product 1,1,1-trifluoro-3-iodopropane. Should he follow his friends advice?

a. Propose a mechanism for the following reaction (show all curved arrows):b. Which step is the rate-determining step? c. What is the electrophile in the first step? d. What is the nucleophile in the first step? e. What is the electrophile in the second step? f. What is the nucleophile in the second step?

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents: a. HBr b. H2, Pd/C c. R2BH/THF, followed by HO, H2O2, H2O d. Br2/CH2Cl2

Which stereoisomer of 3-hexene forms a meso compound when it reacts with Br2?

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?

Propose a mechanism for each of the following reactions:

What is the major product of each of the following reactions?

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed. a. cis-2-pentene + HCl b. trans-2-pentene + HCl c. 1-ethylcyclohexene + H2O + H2SO4 d. 2,3-dimethyl-3-hexene + H2, Pd/C e. 1,2-dimethylcyclohexene + HCl f. 1,2-dideuteriocyclohexene + H2, Pd/C g. 3,3-dimethyl-1-pentene + Br2/CH2Cl2 h. 1E2@3,4@dimethyl@3@heptene + H2, Pd/C i. 1Z2@3,4@dimethyl@3@heptene + H2, Pd/C j. 1@chloro@2@ethylcyclohexene + H2, Pd/C

a. What product is obtained from the reaction of HCl with 1-butene? With 2-butene? b. Which of the two reactions has the greater free energy of activation? c. Which compound reacts more rapidly with HCl: (Z)-2-butene or (E)-2-butene?

What is the major product of the reaction of each of the following with HBr?

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide

Which stereoisomer of 3,4-dimethyl-3-hexene forms (3S,4S)-3,4-dimethylhexane and (3R,4R)-3,4-dimethylhexane when it reacts with H2, Pd/C?

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed. a. cis@2@pentene + Br2>CH2Cl2 b. trans@2@pentene + Br2>CH2Cl2 c. 1@butene + HCl d. methylcyclohexene + HBr e. trans@3@hexene + Br2>CH2Cl2 f. cis@3@hexene + Br2>CH2Cl2 g. 3,3@dimethyl@1@pentene + HBr h. cis@2@butene + HBr i. 1Z2@2,3@dichloro@2@butene + H2, Pd/C j. 1E2@2,3@dichloro@2@butene + H2, Pd/C k. 1Z2@3,4@dimethyl@3@hexene + H2, Pd/C l. 1E2@3,4@dimethyl@3@hexene + H2, Pd/C

Of the possible products shown for the following reaction, are there any that will not be formed?

A, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2 over Pd>C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration>oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C6H10O2. Provide structures for AF.

The reaction of an alkene with diazomethane forms a cyclopropane ring. Propose a mechanism for the reaction. (Hint: It is a concerted reaction.)

Two chemists at Dupont found that ICH2ZnI is better than diazomethane at converting a CC bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the SimmonsSmith reaction in their honor.

a. Dichlorocarbene can be generated by heating chloroform with HO- . Propose a mechanism for the reaction. + HO chloroform dichlorocarbene CHCl3 + H2O  Cl2C + Cl b. Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction. Cl2C sodium trichloroacetate

What product is obtained from the reaction of dichlorocarbene with cyclopentene?

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

Draw the products of the following reactions, including their configurations:

a. Propose a mechanism for the following reaction:b. Is the initially formed carbocation primary, secondary, or tertiary? c. Is the rearranged carbocation primary, secondary, or tertiary? d. Why does the rearrangement occur?

Which compound is hydrated more rapidly?

When the following compound is hydrated in the presence of acid, the unreacted alkene is found to have retained the deuterium atoms. What does this tell you about the mechanism for hydration?

When fumarate reacts with D2O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D2O?

What stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl2?

Propose a mechanism for the following reaction:

What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.