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Interpretation:
The products obtained in each of the given reaction is to be determined.
Concept introduction:
A Diels Ander reaction is one between a conjugate diene and a reactant containing a double bond (dienophile) to form a product. The product is called adduct.
Diels Ander reactions are highly stereospecific. The configuration of the dienophile is retained in the product, and the reaction is a syn addition reaction.
The dienes react with dienophiles in cis forms rather than trans forms.
Endo and exo referto the orientation of the dienophile and its electron-withdrawing group when it reacts with a diene in a Diels Ander reaction.
Endo is favored in the transition state of aDiels Ander reaction because it has a lower energy.
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Chapter 13 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
- Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH 1844 Li NH3 ND3 C=C—CH3 NH3arrow_forwardPractice Problem 12.42b Predict the product and draw a mechanism for the following reaction: NABH, MEOH 12.42b Draw the major organic product.arrow_forwardProvide the necessary reagents to accomplish the desired organic reactions. Please number the steps and note that some reactions will require more than one step. (a) (b) Me Br OMe NH Me ÓTs OMearrow_forward
- Predict the major products of the following reactions, including stereochemistry where appropriate. (a) potassium tert-butoxide + methyl iodide (b) sodium methoxide + tert-butyl iodidearrow_forward3) Propose suitable reagent(s) to accomplish the following transformations. (a) (b) Br N OH orarrow_forwardIdentify the reagents you would use to achieve of the following transformation. Identify these reactions as SN1 or Sn2. (a) (b) (c) (d)arrow_forward
- 15.37 Write mechanisms that account for the products of the following reactions: (a) (b) 15.37 Write mechanisms that account for the products of the following reactions: (a) OH HA (-H₂O) HA (b)arrow_forwardPredict the products for the following reaction (1,2- and 1,4- addition) and propose a mechanism that explains the formation of each product. (1) (2) HCI + (3) (4)arrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (3) OH OH trans-1,2-cyclohexanediol (racemic) Submit Answer (c) ethylene oxide OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: "OH (a) CH₂O¯Na+, CH3OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 Retry Entire Group OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 8 more group attempts remaining (2) (g) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Nextarrow_forward
- (c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: OH (c) ethylene oxide (a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH + (9) H₂ SO4 (anhydrous) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate) PBr3 (PCC) (h) NaOH (N-bromosuccinimide) Previous Nextarrow_forward(a) 9.28 Show how you might synthesize the following compounds from a haloalkane and a nucleophile. CN (b) CN (c) (d) SH SHarrow_forward
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