Interpretation:
For each of the following reaction the route that could reasonably be expected from the starting material to the product is to be provided.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
The condensation reactions in carbonyl, the enolate or enol of a carbonyl group of one compound reacts with the carbonyl group of another compound. The two main types of condensation are Claisen and aldol condensation.
Claisen condensation entails the formation of keto esters through carbon–carbon bond formation.
The Claisen condensation is the carbon–carbon bond formation reaction and is important for the preparation of
In Claisen condensation, the ester of one molecule is added to the carbonyl carbon of another molecule and the formation of
When one ester molecule has no alpha hydrogen, crossed Claisen condensation occurs.
Aldol condensation involves the reaction of enolate of an
An aldol reaction takes place by acid catalysis, and direct dehydration of
A
A chemical reaction that is catalyzed by an base is called base catalyzed reaction.
Aldol reaction is preferred in basic condition over acidic condition as after the aldol condensation, acid catalysis promotes the reaction further.
A carbon–carbon bond formation occurs through aldol condensation reaction.
An aldol reaction takes place in a protic solvent with a base.
Dehydration of aldol addition product leads to the formation of conjugated
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Chapter 19 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Provide 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_forwardShow reagents to bring about each conversion. (c) Br (d) (b) (а) (e) (f) H.arrow_forwardFor each compound below, propose an efficient synthesis using diethyl malonate as a starting material. Provide explanations for each step in the mechanism. (a) (b) `NH2 (c)arrow_forward
- 3) Propose suitable reagent(s) to accomplish the following transformations. (a) (b) Br N OH orarrow_forwardUsing hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) 1,2-dibromohexanearrow_forward4) Aromatic compounds are among the most abundant and versatile in nature. From a synthetic point of view, these compounds, despite their stabilities, are quite useful and can undergo reactions under special conditions and by specific mechanisms, such as the Electrophilic Aromatic Substitution (SAE) and the Nucleophilic Aromatic Substitution (SNAr). Based on this, please answer the following items: (b) How would you prepare the following compounds starting from benzene? Explain the second in a different wayarrow_forward
- 2) Propose suitable reagent(s) to accomplish the following transformations. (a) ف مشن (b) OD گھرarrow_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_forwardPredict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (b) (a) Cl₂ CH₂CH₂OH (a) 1 hv 2 (b) H Br H₂O Na+ SCH3 (c) (d) CI "CH3arrow_forward
- Using 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_forwardSHOW THE STRUCTURES OF THE CARBONYL COMPOUNDS THAT WOULD GIVE THE FOLLOWING ALCOHOLS ON REDUCTION. SHOW ALS0 THE STRUCTURE OF THE PRODUCTS THAT WOULD RESULT BY TREATING THE ALCOHOLS WITH A PERIODINANE AND WITH AQUEOUS ACIDIC CRO 3. (a) (b)arrow_forward(a) Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBR3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.arrow_forward