Organic Chemistry - With Access (Looseleaf) (Custom)
4th Edition
ISBN: 9781259726224
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.77P
Interpretation Introduction
Interpretation:
The structure of the product formed on reaction with
Concept introduction:
The method of spectroscopy is used to identify the structure of the molecule. It is based on the interactions between matter and
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Treatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91(triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and2.60 (septet, 1 H) ppm. What is the structure of V?
Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.
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The 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Identify the ester, explaining how you reach your conclusion.
1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm
13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppm
Chapter 20 Solutions
Organic Chemistry - With Access (Looseleaf) (Custom)
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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- Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardReaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.arrow_forwardAn organic compound B with formula C6H14O has the following: IR Spectroscopy 2974 cm-1, 1080 cm-1 Mass Spectrometry 102 (M+), 87, 73 1H NMR Spectroscopy Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H). Compound B is obtained by the reaction of compound A with NaH followed by CH3CH2Br. The stereochemistry of A is "S" Using this information, deduce a plausible structure for Compound A with correct stereochemistry.arrow_forward
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