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Chapter 20, Problem 20.67P
Interpretation Introduction

Interpretation: The synthesis of the given alcohol from benzene is to be predicted.

Concept introduction: The reaction of alkene with alkyl halide in the presence of lewis acid results in the formation nucleophilic product.

Grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether. The reaction of Grignard reagent with an aldehyde/ketone followed by the hydrolysis yields an alcohol.

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Chapter 20 Solutions

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card

Ch. 20 - Prob. 20.11PCh. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 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 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Problem 20.21 Draw the product of each reaction. ...Ch. 20 - Problem 20.22 Draw the products (including...Ch. 20 - Problem 20.23 What Grignard reagent and carbonyl...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 - Problem 20.28 What ester and Grignard reagent are...Ch. 20 - Prob. 20.29PCh. 20 - Problem 20.30 What reagent is needed to convert ...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Problem 20.34 Draw the product when each compound...Ch. 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 - 20.39 Draw the product formed when is treated...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.41PCh. 20 - 20.42 Draw the products or each reduction...Ch. 20 - Prob. 20.43PCh. 20 - 20.44 Draw all stereoisomers formed in each...Ch. 20 - Prob. 20.45PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.48PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.50PCh. 20 - 20.51 Draw a stepwise mechanism for the following...Ch. 20 - 20.52 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.53PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - 20.57 What ester and Grignard reagent are needed...Ch. 20 - 20.58 What organolithium reagent and carbonyl...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.60PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - 20.62 Synthesize each compound from cyclohexanol...Ch. 20 - 20.63 Convert propan-2-ol into each compound....Ch. 20 - 20.64 Convert benzene into each compound. You may...Ch. 20 - 20.65 Design a synthesis of each compound from...Ch. 20 - 20.66 Synthesize each compound from the given...Ch. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 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 - 20.74 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.75PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.81P
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