Section II. Structure and Mechanism 1. a Sometimes "Polyene" cyclization reactions can be catalyzed by a transition metal. Provide a mechanism for the reaction below. PdLn Me Me MeCN, EtN Me Me
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- 1. Which of the following statements about ethylene (CH2-CH2) molecule is/are false? Both carbons are sp² hybridized. The C=C bond length is shorter than the C-C length in ethane. It has a total of two pi bonds. The entire molecule has a planar geometry. а. b. с. d. 2. Which of the following statements regarding the El mechanism is/are false? Reactions by the El mechanism are unimolecular in the rate-determining step. b. а. Reactions by the El mechanism are generally first order. Reactions by the El mechanism usually occur in one step. Reactions by the El mechanism are multi-step reactions. с. d.reactions. Be sure to show any significant stereochemical details. (a) I. Nall. CS 2. CH,I 3. heat (b) 1. BULI, LICI 2.MeCu(CN)LI (c) CH, Zn-Cu CH,l,, ether (d) CH,CO,H LOET (e) Br Zn, THO.Which of the following compound is expected to burn with sooty flame but classified as aliphatic alkyl halide? O a. CH3CH2CH(CI)CH3 O b. CGH5CH2CH,CI O c. 2-Chloro-2-methylpropane O d. Chlorobenzene
- Meeka X me X OWLv2 | Online teaching X ment/takeCovalentActivity.do?locator-assignment-take&takeAssignmentSessi AGP [Review Topics] [References] Draw a structural formula for the major organic product of the following reaction: CH₂Cl₂ -CH=CHCH3 + Br₂ sited Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. . Do not show stereochemistry in other cases. If enantiomers are formed, just draw one. & SP Ⓒ- 1 30 - IF 11:00 PMCumene -> i. Butyl chloride ii. Dimethyl amine iii. H2, Pt Provide the bond-line structures for the major organic products obtained in each stepIIIC) trans-cyclooctene can be synthesized from cis-cyclooctene with UV light (hv).I Use orbital line diagram to show electronic excitation and arrow-pushing to show how this reaction can occur photochemically. hy
- Q1. Give the structure(s) of the major organic produc(s) of A-H, Show stereochemistry if appropriate. Hz. Pd/C KMnO4. H0. B 1. BH, C 2. NoOH, H,02 C2. CH,OH D HCI E KI, H;PO, KMno HO". G H.2. Clz in CCI4 adds to alkene with the anti-stereochemistry by chloronium ion mechanism. Write a mechanism to account for the formation of a mixture of cis and trans isomers in the following reaction. Ph CI Ph Cl, in CCI, Ph CI + H. CI CIH8. Organic chemistry Text answers and (descriptive structures and / or reaction mechanisms). Explain the chemistry of the carbonyl group (direct addition of nucleophiles and addition with elimination)
- ILkane ring? 15. Discuss the aspects of conformation and stereochemistry that would have considered for complete description of the structure of molecules having the general in these molecules? H. (CH2) H. 16. Predict the preferred conformation of the isomeric (Z- and E-) 3-penten-2-ones, A, R = CH3. How would you expect the conformational picture to change as R becomes progressively larger? Fig the RCCH=CHCH3 V. 17. Figures 17A and 17B (p. 183) show energy as a function of rotation for a series of 2- substituted acetaldehydes, with 0= 0° in the syn conformation and 0 = 180 in the anti conformation. The calculations were done using the PM3 method. Figure 17A IS for a vacuum, whereas Fig. 17B is for a solvent cavity with a dielectric constant of 4.7. structure A. How would the size of the (CH,), bridge affect conformational cquilibriad. e. (Z) (H3C)2N. OCH3 CN[References] Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of…