Organic Chemistry Ch. 8 study guide
Draw a structure for the transition state of the following reaction. Include correct partial charges
Section: 8.7
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail
Section: 8.7
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.7
Provide the structure of the major organic product of the reaction below.
Section: 8.7
Complete the following reaction and provide a detailed, step-by-step mechanism for the process.
Section: 8.8
Provide the major organic product of the reaction below.
Section: 8.15
Provide the structure of the product which results when the alkene below is treated with O3 followed by (CH3)2S.
Section: 8.15
β-Ocimene is a natural product with a pleasant odor. Based on the information below, deduce the structure of β-ocimene.
Section: 8.15
When isobutylene [CH2C(CH3)2] is treated with BF3, polyisobutylene is formed. Provide a step-by-step mechanism for this polymerization reaction.
Section: 8.16
Complete the following reaction and provide a detailed, step-by-step mechanism for the process.
Section: 8.3
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.3
Draw the major regioisomeric product generated in the reaction below.
Section: 8.3
Provide the major organic product of the reaction below.
Section: 8.3
Provide the structure of the major organic product of the reaction below.
Section: 8.3
When 3,6-dimethylcyclohexene is reacted with dry gaseous HBr, one of the products is 1-bromo-1,4-dimethylcyclohexane. Provide a detailed step-by-step mechanism to explain the formation of this product
Section: 8.3
When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of the following structures are formed during the mechanism? A) B) C) D) H∙
Section: 8.3
Complete the following reaction and provide a detailed, step-by-step mechanism for the process
Section: 8.4
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.4
Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.4
Provide the structure of the major organic product of the reaction below.
Section: 8.4
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail
Section: 8.5
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.5
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.6
Provide the structure of the major organic product of the reaction below.
Section: 8.6
Complete the following reaction by filling in the appropriate reagents.
Section: 8.7
Complete the following reaction by filling in the necessary reagents.
Answer: Section: 8.15
Provide the reagents necessary to complete the following transformation.
Answer: 1. Br2, hν 2. H2O, Δ or 1. Br2, hν 2. NaOCH3, CH3OH 3. H3O+ or Hg(OAc)2, H2O; NaBH4 Section: 8.4
Provide the reagents necessary to complete the following transformation.
Answer: 1. Br2, hν 2. NaOCH3, CH3OH 3. CH2I2, Zn(Cu) Section: 8.11
Provide the reagents necessary to complete the following transformation.
Answer: 1. NaOCH3, CH3OH 2. MCPBA or CH3CO3H 3. H3O+ or -OH Section: 8.13
Provide the reagents necessary to complete the following transformation.
Answer: 1. NaOCH3, CH3OH 2. OsO4, H2O2 or cold, dilute KMnO4, -OH Section:8.14
Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol.
Answer: 1. conc. H2SO4 2. H3O+ or Hg(OAc)2, H2O followed by NaBH4 or 1. PBr3 2. NaOCH3, CH3OH 2. H3O+ or Hg(OAc)2, H2O followed by NaBH4 Section: 8.6
Give the structure of the alkene which would yield the following products upon ozonolysis-reduction. CH3COCH3 + CH3CH2CHO
Answer: (CH3)2CCHCH2CH3 Section: 8.15
What alkene, which contains no oxygen atoms and a single CC, will give CH3CO(CH2)4CHO upon treatment with OsO4 followed by cleavage with periodic acid?
Answer: 1-methylcyclohexene Section: 8.15
Name the major alcohol product which results when 3,3-dimethylbut-1-ene is treated with dilute acid.
Answer: 2,3-dimethyl-2-butanol Section: 8.4
Name the major product which results when HBr is added to 3-ethyl-3-hexene.
Answer: 3-bromo-3-ethylhexane Section: 8.3
________ is the use of an optically active reagent or catalyst to convert an optically inactive starting material into an optically active product. A) Asymmetric induction B) Racemization C) Optical reduction D) Meso effection E) Chiralization
Answer: A Section: 8.10
Which of the following steps would successfully complete the following reaction? A) I only B) II & III C) I & IV D) I, II, & IV
Answer: A Section: 8.12
A reaction of an unknown alkene with MCPBA in dichloromethane followed by work-up with H2O/H+ yielded, as the major product, a racemic mixture of (2S, 3S) and (2R, 3R)-3-methylpentan-2,3-diol. What is the specific structure of the alkene used in the reaction? A) (Z)-3-methylpent-2-ene B) (E)-3-methylpent- 2-ene C) 2-methylpent-2-ene D) 2,3-dimethylbut-2-ene E) none of the above
Answer: A Section: 8.13
An unknown compound with empirical formula C3H5 was treated with Br2/CCl4. The bromine solution went from orangish/red to clear immediately at room temperature. Upon treatment with O3 followed by work-up with dimethylsulfide the following products were identified. From the information provided what is/are the most likely structure(s) for this unknown compound.
Answer: A Section: 8.15
What is the expected product of the following reaction?
Answer: A Section: 8.17
When an alkene is subjected to treatment with Hg(OAc)2 in alcohol followed by reaction with NaBH4, what new class of compound is formed? A) ether B) epoxide C) alkane D) syn diol E) alkyne
Answer: A Section: 8.6
Provide the reagents necessary to complete the following transformation. A) 1. BH3∙THF 2. H2O2, HO- B) H2O, H2SO4 C) OsO4, H2O2 D) CH3CO3H E) 1. CH3CO3H 2. H+, H2O
Answer: A Section: 8.7
Addition of Br2 to (E)-hex-3-ene produces ________. A) a meso dibromide B) a mixture of enantiomeric dibromides which is optically active C) a mixture of enantiomeric dibromides which is optically inactive D) (Z)-3,4-dibromo-3-hexene E) (E)-3,4-dibromo-3-hexene
Answer: A Section: 8.8
What olefin metathesis products result when 1-hexene is treated with Grubbs catalyst? What provides the thermodynamic driving force for this reaction?
Answer: A mixture of (E)- and (Z)-5-decene products results. The thermodynamic driving force is the removal of the volatile ethylene by-product. Section: 8.17
Which of the following additions to alkenes occur(s) specifically in an anti fashion? A) hydroboration-oxidation B) addition of Br2 C) addition of H2 D) addition of H2O in dilute acid E) both A and B
Answer: B Diff: 1 Section: 8.8
Treatment of cyclopentene with peroxybenzoic acid ________. A) results in oxidative cleavage of the ring to produce an acyclic compound B) yields a meso epoxide C) yields an equimolar mixture of enantiomeric epoxides D) gives the same product as treatment of cyclopentene with OsO4 E) none of the above
Answer: B Section: 8.12
Predict the major product of the following reaction.
Answer: B Section: 8.3
Provide the reagents necessary to complete the following transformation. A) 1. BH3∙THF 2. H2O2, HO- B) H2O, H2SO4 C) OsO4, H2O2 D) CH3CO3H E) 1. CH3CO3H 2. H+, H2O
Answer: B Section: 8.4
Which of the following intermediates is thought to occur in the mechanism by which alkenes are hydrated in the presence of acid? A) carbanion B) carbocation C) free radical D) carbene E) alkyne
Answer: B Section: 8.4
What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration sequence? A) Markovnikov addition of H2O wherein skeletal rearrangement is promoted B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented C) anti-Markovnikov addition of H2O wherein skeletal rearrangement is promoted D) anti-Markovnikov addition of H2O wherein skeletal rearrangement is prevented E) syn-hydroxylation
Answer: B Section: 8.5
Both (E)- and (Z)-hex-3-ene can be subjected to a hydroboration-oxidation sequence. How are the products from these two reactions related to each other? A) The (E)- and (Z)-isomers generate the same products but in differing amounts. B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts. C) The products of the two isomers are related as constitutional isomers. D) The products of the two isomers are related as diastereomers. E) The products of the two isomers are not structurally related
Answer: B Section: 8.7
Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?
Answer: B Section:8.8
Provide the reagents necessary to complete the following transformation. A) 1. BH3∙THF 2. H2O2, HO- B) H2O, H2SO4 C) OsO4, H2O2 D) CH3CO3H E) 1. CH3CO3H 2. H+, H2O
Answer: C Section: 8.14
How many moles of carbon dioxide are generated when one mole of the compound shown is treated with warm, concentrated KMnO4? A) 1 B) 2 C) 3 D) 4 E) 8
Answer: C Section: 8.15
HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide serve in this reaction? A) nucleophile B) electrophile C) radical chain initiator D) acid catalyst E) solvent
Answer: C Section: 8.3
Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement? A) water + dilute acid B) water + concentrated acid C) oxymercuration-demercuration D) hydroboration-oxidation E) none of the above
Answer: C Section: 8.5
Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H2 reacts with the humulene to produce a monocyclic hydrocarbon of formula C15H30. What is the molecular formula of humulene?
Answer: C15H24 Section: 8.10
Give the structure of the alkene which would yield the following products upon ozonolysis-reduction. CH3CH2CH2CH2CHO + CH2O
Answer: CH3CH2CH2CH2CHCH2 Section: 8.15
Both (E)- and (Z)-hex-3-ene can be treated with D2 in the presence of a platinum catalyst. How are the products from these two reactions related to each other? A) The (E)- and (Z)-isomers generate the same products but in differing amounts. B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts. C) The products of the two isomers are related as constitutional isomers. D) The products of the two isomers are related as diastereomers. E) The products of the two isomers are related as enantiomers.
Answer: D Section: 8.10
What is the major product of the following reaction?
Answer: D Section: 8.4
Provide the reagents necessary to complete the following transformation. A) 1. BH3∙THF 2. H2O2, HO- B) H2O, H2SO4 C) OsO4, H2O2 D) CH3CO3H E) 1. CH3CO3H 2. H+, H2O
Answer: E Section: 8.13
Which of the following compounds is (are) appropriate to promote the cationic polymerization of isobutylene? A) H2SO4 B) BF3 C) ROOR D) NaOH E) both H2SO4 and BF3
Answer: E Section: 8.16
Acid catalyzed hydration (H2SO4/water/△) of an unknown compound (A)with a chemical formula C6H12, yielded a racemic mixture of product C6H13OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)? A) compound 1 only B) compounds 2 and 3 C) compound 2 only D) compounds 1 and 3 E) none of the above
Answer: E Section: 8.4
Treatment of 2-methylpropene with which of the following reaction conditions results in an anti-Markovnikov addition product? A) dry gaseous HBr with peroxides present B) BH3-THF, followed by alkaline H2O2 C) aqueous Hg(OAc)2, followed by alkaline NaBH4 D) dilute H2SO4 and heat E) both A and B
Answer: E Section: 8.7
Which of the following additions to alkenes occur(s) specifically in an syn fashion? A) dihydroxylation using OsO4, H2O2 B) addition of H2 C) hydroboration D) addition of HCl E) A, B, and C
Answer: E Section: 8.14
Ozonolysis-reduction of an unknown alkene gives equal amounts of CH3CH2CHO and CH3CH2CH2CHO. Name the unknown alkene.
Answer: Either (E)- or (Z)-3-heptene Section: 8.15
The following reaction is known to proceed by a free radical chain mechanism. Suggest a reasonable, step-by-step mechanism for this reaction. CH3CHCH2 + CHCl3 CH3CH2CH2CCl3
Answer: ROOR → 2 RO∙ RO∙ + HCCl3 → ROH + ∙CCl3 Cl3C∙ + CH2CHCH3 → Cl3CCH2CH3 Cl3CCH2CH3 + HCCl3 → Cl3CCH2CH2CH3 + ∙CCl3 Section: 8.3
Why can methyl acrylate (H2CCHCO2CH3) be polymerized through anionic polymerization?
Answer: The intermediate carbanion and the transition state leading to it are stabilized by the electron-withdrawing capacity of the carbonyl group. Section: 8.16
Based on the relative stabilities of the intermediates involved, explain the basis for Markovinkov's rule in the addition of hydrogen halides to alkenes.
Answer: The rate-determining step in this reaction is the production of a carbocation intermediate. Since this step is endothermic, Hammond's postulate allows one to gauge the relative stabilities of the transition states by comparing the relative stabilities of the carbocation intermediates. The reaction pathway which produces the more substituted carbocation will thus occur more rapidly. Section: 8.3
Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.
Answer: The reaction proceeds via the addition of Br∙ to the alkene. Two competing pathways are possible, but the transition state leading to the more substituted alkyl radical is lower in energy. This process ultimately makes the addition anti-Markovnikov in nature. Section: 8.3
What cyclic products results when 1,8-nonadiene is treated with Grubbs catalyst?
Answer: cycloheptene Section: 8.17
The mechanism for the acid-catalyzed hydration of alkenes is simply the reverse of the mechanism by which alcohols are dehydrated using concentrated acid. This is an illustration of the principle of ________.
Answer: microscopic reversibility Section: 8.4
Name the compound PhCO3H and give its most common use as a reagent.
Answer: peroxybenzoic acid; an oxidizing agent which converts alkenes to epoxides Section: 8.12
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.10
Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.10
Complete the following reaction by filling in the necessary reagents.
Section: 8.11
Draw the Lewis structure of dibromocarbene.
Section: 8.11
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.11
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.12
Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail
Section: 8.12
Provide the major organic product of the reaction below.
Section: 8.12
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.13
Provide a detailed, step-by-step mechanism for the reaction shown below.
Section: 8.13
Provide the major organic product of the reaction below.
Section: 8.13
Provide the structure of the major organic product of the reaction below.
Section: 8.13
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.14
Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.14
Provide the major organic product of the following reaction.
Section: 8.14
Provide the major organic product of the reaction below.
Section: 8.14
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.15
Predict the structure of the products resulting from the reaction between limonene, a natural terpene found in citrus fruit, and ozone, followed by work up with dimethyl sulfide.
Section: 8.15
Provide the major organic product of the following reaction.
Section: 8.15
Consider how the ICl bond is polarized and predict the product which results when this mixed halogen adds to 1-methylcyclohexene.
Section: 8.8
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail
Section: 8.8
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.8
Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.8
Provide a detailed, step-by-step mechanism for the reaction shown below.
Section: 8.8
Provide the major organic product of the reaction below
Section: 8.8
Complete the following reaction by providing a structure of the expected product. Be sure to indicate all relevant stereochemistry
Section: 8.9
Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.
Section: 8.9
Predict the product of the following reaction. Include any relevant stereochemistry.
Section: 8.9
Provide the structure of the major organic product of the reaction below
Section: 8.9
