FA23 CHEM 225 Exp9 HANDOUT_E2 Rxn_001 (1)

Reaction of propene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Name these two alkyl bromides.

[Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2.

Show a possible stepwise synthesis of 2, 3-dichloropentane starting with ethanol and propanol as the only sources of carbon atoms and any other inorganic reagents, solvents and laboratory equipment. Name the type of reaction that is occurring in each step of the synthesis.

Only one of the chlorine atoms in the molecule, 3,4-dichloronitrobenzene, will undergo nucleophilic substitution. Indicate which position will react and provide the expected product for the given reaction using reaction intermediates (resonance structures).

Functional groups such as alkynes react the same in complex molecules as they do in simpler structures. The following example  of alkyne reaction  were taken from syntheses carried out in the research group of E. J. Corey at Harvard University. You can assume that the reactions listed involve only the alkyne, not any of the functional groups present in the molecules. Draw the expected products for the following reaction .

1. You are planning to carry out a reaction between butyne CH3CH₂C=CH, and sodium methoxide, CH3ONa. You also need to choose an appropriate solvent for the reaction. Would H₂O be an appropriate solvent? Explain your rationale.

i need help drawing the product

Show how you would synthesize each compound from benzene, toluene, or phenol using the following reactions: Reactions 1. Halogenation 2. Nitration 3. Sulfonation 4. Friedel-Crafts acylation 5. Friedel-Crafts alkylation 6. Oxidation of methyl group 7. Reduction of nitro group • Choose the starting material from the drop-down list • Enter the number(s) of the desired reactions in the order that you wish to use them without commas between • If a reaction is used more than once, enter its number each time you wish to use it Compound 1: 5-chloro-2-methylbenzenesulfonic acid Starting material: toluene Reaction(s): 31 Compound 2: m-bromobenzoic acid Starting material: [benzene Reaction(s): Submit Answer Try Another Version 1 item attempt remaining

19. Write a series of equations to illustrate the synthesis of 3-pentanone from an alkene (you must choose the correct alkene compound to begin your series of reactions). Include the names and structures of all reactants and products. (3T/I, 3C)

A lab technician planned to synthesize 2-bromopentane using 2-pentanol, heat, and HBr. However, the labtechnician did not have HBr in the lab. What other reagent(s) can the technician use to synthesize 2-bromopentane using 2-pentanol as the starting material?

4. Synthesize the following compound. You may use benzene, acetylene, ethanol and any inorganic reagents. O₂N

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI H₂N OH • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. Sn [F

10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH3 Br CH3

Select the reagent that you would use to convert an alkene to a Markovnikov (more substituted) alcohol without possibility of carbocation rearrangement. o H2SO4, H2O OBH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4 o OsO4, TBHP, H2O

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI + H₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. OH • Do not include counter-ions, e.g., Na+, I¯, in your answer. • In cases where there is more than one answer, just draw one.

Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product (2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a significant product of this synthesis.

Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. 0 OH CI + H₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. In cases where there is more than one answer, just draw one. A ChemDoodle Activate Windows

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Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CH3OH H3C CI • • • • You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I", in your answer. In cases where there is more than one answer, just draw one.

4. Dissolvable sutures are often used in medicine and dentistry so that additional surgeries don't need to be done to remove the stitches. Two examples of dissolvable sutures are: fart CH2 -CH2 Dexon® and -CH2 -CH2 -CH2 CH, -CH2 PDS® Using the organic chemistry you have learned so far, propose a mechanism for how they dissolve.

3 9 $ 4 R H₂C B % 5 1. Aqueous ethanol HBr CH₁ 2. OH a Proton transfer d E1 Elimination. f = SN1 Nucleophilic substitution b Lewis acid/base. e E2 Elimination g= SN2 Nucleophilic substitution c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a- g for your answers. 1. 2. Submit Answer Retry Entire Group 9 more group attempts remaining Previous Next> Save and Exit Cengage Learning Cengage Technical Support O 8:15 AM 6/20/2022 PrtScn PgDn F5 F6 T B CH₂ Nà Nha ^ 6 Y H N & 7 [Review Topics] H₂C U 8 M CH₂ NH₂ K [References] H₂C 73°F Sunny Home ( 9 O L End 0 G F10 P PgUp 4x F12 □

Draw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <

All of the following are anti-addition reactions with alkenes EXCEPT? 1. MCPBA, 2. H3O+ All reactions result in anti-addition Br₂ H₂, Pt

The Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?

The following can undergo 1,2- or 1,4-addition reactions. Predict the major organic product from each reaction. 1. (CH;CH),CuLi 1. LIAIH, 2. H* 2. H20, H* S' K* 1. CH,M9CI 2. HО, н H20