What alkene should be used to synthesize 3-bromohexane?

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

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

What will be 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:

a. Which is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? b. Which compound would you expect to have the largest heat of hydrogenation? c. Which compound would you expect to have the smallest heat of hydrogenation?

What reagents are needed to synthesize the following alcohols?

Identify each of the following reactions as an oxidation reaction, a reduction reaction, or neither. Cl Cl CH3CH Cl CHCH3 + 2 CH3CHCHCH3 OH CH3CH H CHCH3 + 2O CH3CHCH2

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction. a. CH3CH2C CHCH2CH3 1. O3, 78 C 2. Zn, CH3CO2H CH3 b. CH3CHCH CHCH3 CH3 H2 Pd/C c. CH3 2. (CH3)2S 1. O3, 78 C

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.

Problem 40 in Chapter 5 asked you to d raw the structures for all the alkenes with molecular formula C6H12. Use those structures to answer the following questions: a. Which of the compounds is the most stable? b. Which of the compounds is the least stable?

Draw curved arrows to show the l ow of electrons responsible for the conversion of the following reactants into products.

What reagents are needed to carry out the following syntheses?

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?

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+ .)

Which is more stable?

a. Draw the product or products that would 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. Br 2 in CH 2 Cl 2 7. H2O + H2SO4 2. BH 3 /THF followed by HO- , H 2 O 2 , H 2 O 5. Br2 + H2O 8. CH3OH + H2SO4 3. a peroxyacid 6. H2 + Pd/C b. With which reagents do the two alkenes react to form different products?

The second-order rate constant (in units of M-1 s -1 ) for acid-catalyzed hydration at 25 C is given for each of the following alkenes: CH2 4.95 x 108 8.32 x 108 3.51 x 108 2.15 x 104 3.42 x 104 H3C H C H3C H3C CH3 CH3 C C H3C H CH3 CH3 C C H3C H H CH3 C C H3C H CH3 H C C 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-tril uoropropene when he realized that the labels had fallen off his l asks and he did not know which label belonged to which l ask. 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 l ask containing the most product 1,1,1-tril uoro-2-iodopropane and label the l ask containing the least amount of product 1,1,1- tril uoro- 3- iodopropane. Should he follow his friends advice?

a. Propose a mechanism for the following reaction (show all curved arrows): H2SO4 CH3CH2CH CH2 + CH3OH CH3CH2CHCH3 OCH3 b. Which step is the rate-determining step? e. What is the electrophile in the second step? c. What is the electrophile in the i rst step? f. What is the nucleophile in the second step? d. What is the nucleophile in the i rst step?

Draw the products, including their coni gurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents: a. HBr b. H 2 , Pd/C c. R 2 BH/THF followed by HO , H 2 O 2 , H 2 O d. Br 2 /CH 2 Cl 2

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

Which stereoisomer of 3-hexene forms (3 S ,4 S )-4-bromo-3-hexanol and (3 R ,4 R )-4-bromo-3- hexanol when it reacts with Br 2 and H 2 O?

Propose a mechanism for each of the following reactions: + + Cl a. b. OH

What is the major product of each of the following reactions? CH2Cl2 CH2Cl2

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed. a. cis -2-pentene + HCl f. 1,2-dideuteriocyclohexene + H 2 , Pd/C b. trans -2-pentene + HCl g. 3,3-dimethyl-1-pentene + Br 2 /CH 2 Cl 2 c. 1-ethylcyclohexene + H 2 O + H 2 SO 4 h. 1E2@3,4@dimethyl@3@heptene + H2 , Pd/C d. 2,3-dimethyl-3-hexene + H 2 , Pd/C i. 1Z2@3,4@dimethyl@3@heptene + H2 , Pd/C e. 1,2-dimethylcyclohexene + HCl 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 would be 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 suli de

Which stereoisomer of 3,4-dimethyl-3-hexene forms (3 S ,4 S )-3,4-dimethylhexane and (3 R ,4 R )- 3,4-dimethylhexane when it reacts with H 2 , Pd/C?

a. How many alkenes could you treat with H 2 , Pd/C in order to prepare methylcyclopentane? b. Which of the alkenes is the most stable? c. Which of the alkenes has the smallest heat of hydrogenation?

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 would not be formed?

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

Two chemists at Dupont found that ICH 2 ZnI 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.

What product would be obtained from the reaction of dichlorocarbene with cyclopentene?

What alkene gives the product shown after reaction i rst with ozone and then with dimethyl suli de

Draw the products of the following reactions including their coni gurations:

. a. Propose a mechanism for the following reaction: Br HBr Br + + 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 would you expect to be 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 D 2 O 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 D 2 O?

When ( S )-(+)-1-chloro-2-methylbutane reacts with chlorine, one of the products is ()-1,4-dichloro-2- methylbutane. Does this product have the R or the S coni guration?

Propose a mechanism for the following reaction

What hydrocarbon would form the following products after reaction i rst with ozone and then with dimethyl suli de?

Ozonolysis of an alkene, followed by treatment with dimethyl suli de, forms the following product(s). Identify the alkene in each case. a. O O O O H b. O H O O O + H

Problem 3P a. How many ? bond orbitals are available for overlap with the vacant p orbital in 1. the isobutyl cation? 2. the n-butyl cation? 3. the sec-butyl cation? b. Which of the carbocations in part a is most stable?

List the following carbocations in each set in order from most stable to least stable:

Will the structure of the transition state in the following reaction coordinate diagrams be more similar to the structure of the reactants or to the structure of the products?

What is the major product obtained from the reaction of \(H B r\) with each of the following? Equation Transcription: Text Transcription: HBr

Problem 18P Which is more highly regioselective, reaction of an alkene with BH3 or with 9-BBN?

Problem 19P What would be the major product obtained from hydroboration–oxidation of the following alkenes? a. 2-methyl-2-butene b. 1-methylcyclohexene

What products are formed when the following compound react with ozone and then with dimethyl sulfide?

Problem 30P a. What alkene would give only a ketone with three carbons as a product of oxidative cleavage? b. What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage?

Problem 31P What aspect of the structure of the alkene does ozonolysis not tell you?

Problem 46P What stereoisomers are obtained from hydroboration–oxidation of the following compounds? a. cyclohexene c. cis-2-butene b. 1-ethylcyclohexene d. (Z)-3,4-dimethyl-3-hexene

Problem 47P The reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.

Problem 49P What stereoisomers are obtained from the following reactions? a. trans-2-butene + HBr d. cis-3-hexene + HBr b. (Z)-3-methyl-2-pentene + HBr e. cis-2-pentene + Br2 c. (E)-3-methyl-2-pentene + HBr f. 1-hexene + Br2

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

Problem 61P What will be the major product of the reaction of 2-methyl-2-butene with each of the following reagents? a. HBrb. HIc. Cl2/CH2Cl2d. O3, ?78 °C, followed by (CH3)2Se. H2/Pdf. MCPBA (a peroxyacid)g. H2O + H2SO4h. Br2/CH2Cl2i. Br2/H2Oj. Br2/CH3OHk. BH3/THF, followed by H2O2, HO-, H2O

Give two names for each of the following:

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

Problem 73P 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+.)

Which is more stable?

Propose a mechanism for each of the following reactions:

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

Problem 86P Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed. a. cis-2-pentene + HCl f. 1,2-dideuteriocyclohexene + H2, Pd/C b. trans-2-pentene + HCl g. 3,3-dimethyl-1-pentene + Br2/CH2Cl2 c. 1-ethylcyclohexene + H2O + H2SO4 h. (E)-3,4-dimethyl-3-heptene + H2, Pd/C d. 2,3-dimethyl-3-hexene + H2, Pd/C i. (Z)-3,4-dimethyl-3-heptene + H2, Pd/C e. 1,2-dimethylcyclohexene + HCl j. 1-chloro-2-ethylcyclohexene + H2, Pd/C

Problem 97P What product would be obtained from the reaction of dichlorocarbene with cyclopentene?

a. Dichlorocarbene can be generated by heating chloroform with \(\mathrm{HO}^{-}\). Propose a mechanism for the reaction. b. Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction. Equation Transcription: Text Transcription: HO^-

What alkene gives the product shown after reaction i rst with ozone and then with dimethyl sulfide

What would be the major product obtained from the addition of \(H B r\) to each of the following compounds? Equation Transcription: Text Transcription: HBr

What alkene should be used to synthesize each of the following alkyl bromides?

To which compound is the addition of \(H B r\) more highly regioselective? Equation Transcription: Text Transcription: HBr

What would be the product of the preceding reaction if \(H B r\) were used in place of \(B r_{2}\)? Equation Transcription: Text Transcription: HBr Br_2

Problem 21P a. How does the first step in the reaction of propene with Br2 differ from the first step in the reaction of propene with HBr? b. To understand why Br- attacks a carbon of the bromonium ion rather than the positively charged bromine, draw the product that would be obtained if Br- did attack bromine.

Problem 22P Why are Na+ and K+ unable to form covalent bonds?

Problem 34P What alkene would you start with if you wanted to synthesize a. Pentane? b. ethylcyclopentane?

Problem 35P How many different alkenes can be hydrogenated to form a. butane? b. 3-methylpentane? c. hexane?

Problem 36P The same alkane is obtained from the catalytic hydrogenation of both alkene A and alkene B. The heat of hydrogenation of alkene A is 29.8 kcal/mol, and the heat of hydro-genation of alkene B is 31.4 kcal/mol. Which alkene is more stable?

Problem 50P When Br2 adds to a cis alkene that has different substituents attached to each of the two sp2 carbons, such as cis-2-heptene, identical amounts of the two threo enantiomers are obtained even though Br- is more likely to attack the less sterically hindered carbon of the bromonium ion. Explain why identical amounts of the two enantiomers are obtained.

Problem 51P a. What products would be obtained from the addition of Br2 to cyclohexene if H2O were added to the reaction mixture? b. Propose a mechanism for the reaction.

What stereoisomers would you expect to obtain from each of the following reactions?

Problem 63P a. Which is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? b. Which compound would you expect to have the largest heat of hydrogenation? c. Which compound would you expect to have the smallest heat of hydrogenation?

Identify each of the following reactions as an oxidation reaction, a reduction reaction, or neither.

What reagents are needed to synthesize the following alcohols?

Problem 75P a. Draw the product or products that would 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 b. With which reagents do the two alkenes react to form different products?

The second-order rate constant (in units of \(M^{-1} s^{-1}\)) for acid-catalyzed hydration at \(25^{\circ} \mathrm{C}\) 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: \(3.51 \times 10^{-8}\).) 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? Equation Transcription: ° Text Transcription: M^-1 s^-1 25 degree C 3.51 times 10^-8

Which compound has the greater dipole moment?

Problem 87P 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 would be the major product of the reaction of each of the following with \(H B r\)? Equation Transcription: Text Transcription: HBr

For each compound, show the products obtained from ozonolysis, followed by treatment 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 would you expect to be hydrated more rapidly?

Problem 9P The pKa of a protonated alcohol is about -2.5, and the pKa of an alcohol is about 15. Therefore, as long as the pH of the solution is greater than _______ and less than _______, more than 50% of 2-propanol (the product of the reaction on page 247) will be in its neutral, nonprotonated form.

Problem 10P Answer the following questions about the mechanism for the acid-catalyzed hydration of an alkene: a. How many transition states are there? b. How many intermediates are there? c. Which step in the forward direction has the smallest rate constant?

What is the major product obtained from the acid-catalyzed hydration of each of the following alkenes?

Each of the following reactions has two nucleophiles that could add to the intermediate fromed by the reaction of the alkene with an electrophile. What will be the major product of each reaction?

What is the product of the addition of \(I-C 1 \text { to } 1\)-butene? (Hint: Chlorine is more electronegative than iodine [Table \(1.3\) ].) Equation Transcription: Text Transcription: I-C1 to 1 1.3

What minimum percent of naproxen is obtained as the \(S\) enantiomer in the synthesis shown in the preceding box? Equation Transcription: Text Transcription: S

Problem 55P a. What would be the product of the reaction of fumarate and H2O if an acid were used as a catalyst instead of fumarase? ________________ b. What would be the product of the reaction of maleate and H2O if an acid were used as a catalyst instead of fumarase?

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

Problem 67P 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.

Problem 68P Problem 40 in Chapter 5 asked you to draw the structures for all the alkenes with molecular formula C6H12. Use those structures to answer the following questions: a. Which of the compounds is the most stable? b. Which of the compounds is the least stable? Reference: Problem 40: a. Draw the condensed structures and give the systematic names for all the alkenes with molecular formula C6H12, ignoring stereoisomers. (Hint: There are 13.) b. Which of the compounds have E and Z isomers?

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

Problem 79P 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 friend’s advice?

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

Problem 90P 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?

Problem 91P a. How many alkenes could you treat with H2, Pd/C in order to prepare methylcyclopentane? b. Which of the alkenes is the most stable? c. Which of the alkenes has the smallest heat of hydrogenation?

Problem 25P What would be the major product obtained from the reaction of Br2 with 1-butene if the reaction were carried out in a. Dichloromethane? b. Water? c. ethyl alcohol? d. methyl alcohol?

a. Which of the following compounds is the most stable? b. Which is the least stable? c. Which has the smallest heat of hydrogenation?

Problem 38P Rank the following compounds in order from most stable to least stable: trans-3-hexene, cis-3-hexene, cis-2,5-dimethyl-3-hexene, cis-3,4-dimethyl-3-hexene

Problem 39P What characteristics must the reactant of a stereospecific reaction have?

Problem 53P a. What is the major product obtained from the reaction of propene and Br2 plus excess Cl- ? b. Indicate the relative amounts of the stereoisomers that are obtained.

Problem 92P 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. (Z)-2,3-dichloro-2-butene + H2, Pd/C j. (E)-2,3-dichloro-2-butene + H2, Pd/C k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C l. (E)-3,4-dimethyl-3-hexene + H2, Pd/C

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 \(D_{2} O\) 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 \(D_{2} O\)? Equation Transcription: Text Transcription: D_2 O

Problem 104P What stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl2?

Problem 1P Draw the mechanism for the reaction of cyclohexene with HCl.

Problem 2P a. How many ? bond orbitals are available for overlap with the vacant p orbital in the methyl cation? b. Which is more stable, a methyl cation or an ethyl cation? Why?

a. What is the major product of each of the following reactions? b. What do all the reactions have in common? c. How do all the reactions differ?

How could the following compounds be prepared, using an alkene as one of the starting materials?

Propose a mechanism for the following reaction (remember to use curved arrows to show the movement of electrons from the nucleophile to the electrophile):

Propose a mechanism for the following reaction:

Problem 27P Draw the structures for the following compounds: a. 2-propyloxirane c. 2,2,3,3-tetramethyloxirane b. cyclohexene oxide d. 2,3-epoxy-2-methylpentane

What alkene would you treat with a peroxyacid in order to obtain each of the following epoxides?

Problem 40P a. Is the reaction of 2-butene with HBr regioselective? b. Is it stereoselective? c. Is it stereospecific? d. Is the reaction of 1-butene with HBr regioselective? e. Is it stereoselective? f. Is it stereospecific?

What stereoisomers are obtained from each of the following reactions?

a. What alkene is required to synthesize each of the following compounds? b. What other epoxide would be formed?

Explain why \(3\)-methylcyclohexene should not be used as the starting material in Problem \(56 b\). Equation Transcription: Text Transcription: 3 56b

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

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

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?

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

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents: a. HBr b. \(H_2\), Pd/C c. \(R_{2}BH/THF\) followed by \(HO^–\), \(H_{2}O_{2}\), \(H_{2}O\) d. \(Br_{2}/CH_{2}Cl_{2}\)

Which stereoisomer of 3-hexene forms a meso compound when it reacts with \(Br_2\)?

Problem 83P 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?

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

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

Problem 95P Two chemists at Dupont found that ICH2ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.

Propose a mechanism for the following reaction:

What hydrocarbon would form 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.