FA23 CHEM 225 Exp9 HANDOUT_E2 Rxn_001 (1)

10. Terpene is a class of naturally occurring molecules, found in many essential oils from plants, that share the same alkene features. All terpenes have a similar 5 carbon unit that includes an alkene thought to be biologically synthesized from the molecule isoprene. All terpenes are biosynthesized from molecules with the good leaving group: pyrophosphate (OPP). Loss of this OPP leads to the formation of a resonance stabilized carbocation. The new carbocation can undergo a nucleophilic attack from a T-bond as seen in acid-catalyzed hydration and hydrohalogenation, forming a new carbocation. This new carbocation can undergo an E1 reaction to form a new alkene. Add the curved arrows of the following reaction. hopp COPP D 5 R-carvone (spearmint oil) - Q Search 40 6 & COPP 1 COPP COPP

The conversion of alcohols into alkyl halides by reaction with hydrogen halides is an example of a Nucleophilic Substitution Reaction. This kind of reaction can proceed by two different mechanisms depending on the structure of alcohol substrates used. Generally, primary alcohols are substituted via SN2 mechanism, while secondary and tertiary alcohols undergo SN1 mechanism. Consider the following reaction given in the picture below and the questions in the picture too.

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 .

Chemistry

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

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?

Chemistry 3. The following sequence generates crystals. The crystals produced are insoluble in organic solvents but freely soluble in water. They have a melting point of 203 °C. There is an instantaneous precipitate formed with silver nitrate solution. Catalytic hydrogenation gives cycloheptane. What is the crystalline compound? Why does it have these unexpected properties? heat 1 equiv Br2 dibromide crystals - HBr tropilidene

1. Predict the product(s) and propose a mechanism of the following nucleophilic substitution reaction. Remember that a mechanism should contain arrows to show movement of electrons, all intermediates and appropriate formal charges. Br + H₂O →

Chemistry Part 5 out of 6 Choose the most appropriate reagent(s) for the conversion of 1-phenylethyl bromide to methyl 1-phenylethyl sulfide. A H₂S C CH₂SH NBS, ROOR CCI4 heat E CH₂SO₂H Br BSg, NaOH reagent(s) DNaSCH3, DMF SCH3

Consider the reaction below to answer the following questions. When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed. Cl. CL CH₂ ( H₂C H C=C H + CHCl3 KOH H₂C--- CH3 H H Write the complete stepwise mechanism for the formation of dichlorocarbene, :CCl₂. Show all intermediate structures and show all electron flow with arrows.

CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*

4. When analyzing a synthesis, it is extremely important to identify functional groups and the reactions that can make them. Fill in the following chart for the functional groups you learned to make this semester. Note that there may be more than one answer, and that X = Cl or Br here. Functional Group Starting Material = alkyne E-alkene (trans) Z-alkene (cis) Å epoxide X two anti halogens on adjacent carbons НО anti halohydrin OH alcohol, most substituted carbon OH alcohol, least substituted carbon halide, most substituted carbon .X halide, least substituted carbon Reagents

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● VIL ? ChemDoodle Ⓡ Qt Sn [F

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.

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Ⓡ <

H NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 2-methyl-2-butanol as the MAJOR product. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.

In SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.

Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in liquid ammonia, followed by 1-bromopropane. The starting hydrocarbon must have no more than five carbons 1) NaNH2, NH3() NaBr + 2) CHзCH2CH2Br

4.) HX is used as a reagent in the reaction below. „NH2 он + HX + :NEN: + A. What functional-group transformation occurs in this reaction?

What would be the first reaction in this synthesis reaction? Friedel-Craft Alkylation Friedel-Craft Acylation Halogenation Oxidation using KMnO4 Sulfonation

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 .

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.

help me please Please fill in the reagents,intermediates, and/or products of the following reactions.     all the reactions shall be covered in Chapter 12-15 from Organic Chemistry, 6th Edition by Marc Loudon and Jim Parise.